I first met Jamie Clayton when a friend of mine, who I had previously known to be something of a connoisseur of beautiful women of the traditional variety, announced he was dating a "super-cool," "totally fucking hot" transsexual. The fiery-haired, freckled Ms. Clayton came out in this space on August 28, 2008, after we met at a trendy Union Square diner. On a recent Thursday afternoon, we met there again for lunch.

"Oh my God, everything changed after the article," she said, between bites of an egg-white omelet with a side of fruit. The story spread across the blogosphere, recalled Ms. Clayton, now 32, beginning with a post on Gawker and proceeding into more esoteric Internet cul-de-sacs. All of the sudden, a transgender community she didn't know existed was embracing her as a role model.

"I was getting emails from all over the world," she said. Australia, London, Asia especially. Transgender ladies wrote to express gratitude for her courage. Men communicated their desire for a piece of her. She was invited to go on The Tyra Banks Show. CBS News' Logo Channel did a segment on her.

Ms. Clayton got new head shots. The photographer was also an acting coach. After two months of classes, and after running into Laverne Cox, a transsexual gal who had produced a reality show with P. Diddy and seen Ms. Clayton on Tyra, she was cast on a reality-show pilot for VH1 called TRANSform Me, a makeover show featuring three transsexual fashion professionals coming to the aid of XX women. "I thought that you were stealth," Ms. Cox had said. Meaning undercover. Not anymore!

VH1 ORDERED EIGHT episodes of TRANSform Me, which debuted in February. The network told her it was the best-reviewed reality show the network had put out. "The show is breaking new ground by presenting transgendered women as fierce and fabulous-if a little superficial," Village Voice columnist Michael Musto told ABCNews.com.

The transgender community largely agreed. The most exhaustive analyses came from the disciples of the ever-evolving New Feminist movement. "The three leads give cis women makeovers while relating these women's experiences to their transition," began the critique on Feministing.com. ("Cis," from the Latin prefix meaning "to be on the same side," is a term in women's studies departments across academia to describe women who were born with a vagina.) The author, Jos, opined that TRANSform Me was nevertheless a net-positive, commendable for its overriding message that "a physical makeover is really just one part of changing how someone sees themselves."

In the comments section, there ensued a theoretical catfight of sorts: The transgender's rightful place in the pantheon of female oppression? Discuss!

"Being cis and female can mean being born just to be killed ... being raped for the rest of your life ... being sold into marriage with some old misogynistic dude who's itching to get your [sic] pregnant at the first sign of menstruation," noted one commenter on March 19, 2010.

"I would eat shit every day for 10 years to have your cisgender body," responded another.

It was gibberish to Ms. Clayton, who had never before heard the term "cis," though she'd gotten a taste of p.c. when VH1 subjected the trio to a GLAAD media training session in which they were informed that the word "tranny" is not kosher.

Jamie thinks it's fine if used in a positive way, as in "that tranny is fierce." 

"It's getting better but people are still uncomfortable," she said. "You say the word 'transgender' or 'transsexual' and people sort of go, 'Oh, don't talk about that.'" 

And yet! In January, President Obama tapped Amanda Simpson as senior technical adviser in the Commerce Department's Bureau of Industry and Security, making her the first openly transgender cabinet appointee. In April, The New York Times' City Room blog introduced Answers About Transgender Issues, a three-part series in which one Dr. Laura Erickson-Schroth hoped to create a "resource guide for transgender and other gender-variant people."

Ms. Clayton was hounded by fans while on line for a latte at the local Starbucks while visiting her mother in Seattle. Outside a coffee shoe in the East Village, a bunch of gay boys ID'd Her Fierceness and began chanting, "Work it bitch! Work it bitch! You're beautiful, bitch."

Ms. Clayton's surgery (six hours, $16,000) took place at her family vacation place outside Tucson, fortuitously home to Dr. Toby Meltzer's world-renowned clinic. "She's become a spokesperson for so many other girls like her," her sister Toni said proudly.

She does have some concern her sister will end up in a dumpster, or like the trans-woman she recently read about who was found dismembered in a park in Queens. According to one academic study, 48 percent of transgender folks are victims of assault, including rape. "We're like the last group of people that sort of really need to be accepted," Ms. Clayton said.

SEVERAL CASTING DIRECTORS, however, have told her she's not transsexual enough. In June, Ms. Clayton was a guest on Qtalk. A man in the audience asked if she dated gay men. "I think that transgender people are constantly sort of sexualized because what we're doing has to do with our genitals and so people sexualize that," she said, "but it really has nothing to do with sex."

I asked her if she had had many orgasms lately. "Yes, I have," she said, with a blush and a hearty laugh. "A lot of women, whether they're transgender or not, go through a period of learning how their body works and let's just say that I know how mine works and that it does. Thank you, Dr. Meltzer. I'll leave it at that."

O.K., then! But what of romantic love?  "I'm newly single," Ms. Clayton said. Her most recent relationship, with an actor named Joey Almanza, began in May of last year and ended in February. "He was great. He was amazing. I mean, we were totally in love with each other."

Mr. Almanza, 27, an actor, first laid eyes on Ms. Clayton at a dinner party at Lucky Cheng's in the East Village. At the time, he was DJing at Mavra, which shares a hallway with the drag club. "They're not supposed to come over to the other side, but Jamie and this other girl sort of got a pass because they were pretty, the other ones were freak shows," Mr. Almanza said over the phone. "So we would meet up in the hallway and do shots and kiss."

"In the bathroom with your feet in the drawers," Ms. Clayton gushed. "It's just that sort of chemical physical attraction that you have,"

Mr. Almanza said that while they were dating, some friends, girls especially, were curious about Jamie's "mechanics." A girl he used to hook up with texted "Post or Pre?" after seeing him with his new squeeze at a party. I asked him if he was surprised at his attraction to a transsexual woman.

"It didn't feel like she was one," Mr. Almanza said. "Maybe a little smaller," he allowed. A friend had asked him how he dealt with "the equipment." "The equipment wasn't there. She was just a normal girl. As far as alarms that go off as a guy, they don't go off."

He speculated that Ms. Clayton was unique in this way. "I've never been attracted to any others; I don't think there are any others like her."

But shortly after TRANSform Me aired, Ms. Clayton realized Joey wasn't the "end-all, be-all." 

Her friend Michelle has assumed the role of de facto assistant, screening her emails and updating her Web site, jamieclayton.net. Rae emailed in March on behalf of the Translating Identity Conference (TIC) at the University of Vermont. Ms. Clayton is slated to be the keynote speaker this fall.

My friend Ryan, whose nine-month-long relationship with Jamie was her first after going under the knife, says he thinks Ms. Clayton has "helped us make baby steps, culturally, and has definitely made the world safer for transgender women."

editorial@observer.com

“Dear Vahram,” began the inquiry. “I am looking for a new tailor and was wondering whether you can make a suit along the following lines: Single breasted, 1 button; Conservative, but reasonably shaped with suppressed waste; Soft shoulders with limited padding and a bit of roping; High armholes; High notch lapel collar; 4 working sleeve buttonholes; full canvas lining; hand stitched lapels; and waist adjusters on the pants.”

What passes between man and tailor is traditionally sacred, and Mr. Mateosian would only allow that the author of this missive—one of a number offered as evidence of a curious shift he’s observed in the city’s fashionable men—appeared to be in his 30s and lived in New York. He might have made a note of the fellow’s profession had there been anything out of the ordinary about his request.

“I received the two pairs of pants tonight. Everything looks good, but I have one change I’d like to make,” reads another piece of forwarded correspondence, this one dispatched at 10:33 p.m. on a Tuesday in mid-January by a dandy by the name of Jon. “I’d like them a bit more tapered in the lower leg (from knee to ankle). Currently the ankle measures at 9 1/4 (18 1/2 total), which swallows up my shoes a little (I wear a 8 1/2 - 9 shoe). What ankle measurement would you suggest?”

Open since 1965, Mr. Ned is one of most popular custom tailors in New York, running at a clip of about 40 suits a week, but Vahram said he only began getting these kinds of highly specific sartorial instructions about two years ago. “It’s become almost normal,” he said. “I get emails like these every day.”

But whatever does it mean?!

From the confines of a swivel chair behind the desk tucked into corner of his no-frills mini-factory, the tailor shrugged his broad shoulders. “It makes my job easier,” he said.

RECESSION OR NO, the bespoke suit, once a special privilege of the very rich (it typically costs $2,000 plus three fitting sessions), has gained a toehold among the upper-middle class. A sort of Men’s Warehouse of made-to-measure suits called My.Suit just opened up two stores in town, offering suits for $495 a pop! (In this case, “made-to-measure” means you hope the factory will interpret the measurements properly and you’ll like what you see when it comes back from Indonesia. It’s not a custom suit, but it’s close enough to keep the promise of the bespoke renaissance alive.)

Mr. Ned is something different. Vahram is perhaps best known for outfitting the director Wes Anderson, but the bulk of his clientele is still bankers and, to a lesser extent, lawyers, as was the case in 1964, when his father, Nuran—who went by Ned—began selling suits door-to-door in the evenings, after putting in a day’s work as a fabric cutter. Nuran eventually built his name as Wall Street’s best-kept secret. Quality custom tailoring, at affordable prices—shhhh! Affordable for Ned means $850—about what it costs for a decent suit at Brooks Brothers—for a two-piece cut of the cloth he keeps in stock. It is true that Mr. Mateosian’s handiwork is now reaching far beyond the world of finance, but he’s hoping the unprecedented shift in the way his clients talk is reflective of an enthusiasm that will result in a more significant return. Still, it’s nice to see new faces: architects, bar mitzvah, the children’s musician Dan Zanes! 

SLIDESHOW: Inside the Mr. Ned Atelier >

The saxophone player Jason Marshall, 26, a rising star who cites Miles Davis as a style influence, began getting his suits from Mr. Ned about a year ago, partly because of admiring P. Diddy’s former valet, Fonzworth Bentley. “There’s definitely been a movement towards taking a more serious interest in your appearance,” Mr. Marshall said. He sees it in the other musicians he plays with, many of whom he’s referred to Mr. Ned. “The thing about dressing up and looking sharp before you leave the house … It’s hard to be a jerk in a custom-made suit.”

(Clearly, Mr. Marshall has not been watching Mad Men. His sentiment is nice, but it’s pure nonsense.)
Michael Goody, a 33-year-old finance man, gave Mr. Ned a shot after an article about his services to Mr. Anderson pricked his nostalgia. “I grew up watching my father argue with his tailor,” he said. Mr. Goody recently got a purple tweed blazer made as an homage to one his grandfather wore. 

Ridiculous (or completely awesome) as a purple tweed might sound, Mr. Goody couldn’t care less. The trends may have helped fan the sails, but the anchor of family tradition keeps him from feeling crazy when staring at mensstyleforum.com past bedtime. Even his wife makes little jokes about his sexuality, but Mr. Goody is comfortable with his passion for wide-lapeled coats with one button—and, yes, a reasonably suppressed waistline—to accommodate his breadth.   

MR. MATEOSIAN MAKES suits for these young turkeys, but he doesn’t live in the city they exist to conquer. Instead, he resides in rather leafy Bergen County, N.J., not far from where he grew up, with his wife, whom he met in high school, and their two dogs. On weekends he plays in a soccer league on a team consisting mainly of men who are, like him, of Armenian descent.

Custom tailoring already had begun inch-worming its way out of the province of old boys and prodigal sons to the high ground of hipness when Nuran handed Vahram the business 10 years ago. It was right around that time that NBA power forward Charles Oakley became a customer, ordering 100 different flamboyant varietals in three years alone. Mr. Oakley turned the sports world into a four-button snow cone, with a steady stream of assists to Mr. Ned’s business. 

“Rest assured,” Vahram assures new clients on the Mr. Ned Web site. “I personally have over 15 years experience in making custom made clothing.” He bares little resemblance to the impeccably attired Jeeves-type characters that swish about the lush carpets in the back rooms of Paul Stuart and Jay Kos. Also: There is no carpet on which to swish.

It’s a simple space, four walls that look like they haven’t been painted since the business started, utterly devoid of polished mahogany moldings or sumptuous leathers chairs. The sweatshop in the back adds a different kind of flavor. The front is all piles of fabric. The Spartan surroundings confer an intoxicating aura upon the wooden pedestal facing a giant mirror and the plentiful bounty beyond, including 20 different blue varietals and enough patterns to make a man keenly aware of the power of his own vanity.

It’s an exhausting business. Nuran, 76, now spends as much time as possible fishing at his vacation place on the North Fork.

“Men’s suits don’t ever change, really,” he said. “It’s either one button or two buttons, double-breasted, single-breasted, one vent or two vents.”

Nuran was being modest. He knows all too well that a custom tailor’s real challenge lies in the fabric between the buttons and the vents. But tailoring, to his mind, was the province of the poor and uneducated. “I never thought my son would choose to be a tailor,” he said.
In college, Vahram studied business, but soccer was his passion. After a few years futzing around in real estate, he asked his dad if he could give Mr. Ned a shot. He liked being in the shop and learning the craft. It wasn’t until a year or two later when he discovered the intense emotion that a nice-fitting suit can bring about in a man. 

The younger Mr. Mateosian wound up putting a ton of miles on his Dodge Caravan to accommodate Mr. Oakley’s latest whim. Now Vahram drives a Mercedes S500, 40 minutes each way to and from the city. “I don’t have kids, so I spend it on me and my wife,” he said. “I love it. I love the car. I absolutely love it.”

He also loves seeing the transformation that takes place when a certain kind of man puts on the suit made for his precise measurements. But Vahram is not that man, nor was his father. He was brought up with a culture strong enough to withstand the tides of fashion that currently has droves of metrosexuals feeling betrayed by their hair gels and Equinox membership cards and frantically trying to find that traditional yet more tailored look. Therein lies a legitimate problem: Not all shapes and sizes can be found on the racks, and it’s not easy to fashion a ill-fitting suit into one that fits like a glove.  

Vahram now believes that Mr. Anderson’s 2001 movie, The Royal Tenenbaums, manifested a new frontier in men’s fashion. He says that when the director told him what he wanted, he spoke frankly, as Vahram always does. “I told him I didn’t think it was going to work,” he said. “But when he put it on—he proved me wrong. I love it when that happens.”

SLIDESHOW: Inside the Mr. Ned Atelier >

editorial@observer.com

Mr. Paris, 72, knows his way around a piece.

“Toupee, hair piece, hair graft, whatever name they come up with next to call it,” he said from the confines of a beautiful leather chair behind a large, expensive-looking mahogany desk. “They’re all selling the same thing.”

Name a male public figure with a suspicious hairline, and chances are Mr. Paris has measured his scalp from all four sides: Burt Reynolds, Charlie Sheen (it was for a movie—before Mr. Sheen started wearing a toupee in real life). Not, however, Peter Orszag, the 41-year-old director of the Office of Management and Budget, whose surprising prowess with the female gender has brought attention to the furry suitcase balanced on the top of his head.

“He looks ridiculous!” Mr. Paris cried, when I pulled up the gotcha! photo gallery published on the Huffington Post. “If he ever gets stranded on an island, he better be careful. After awhile, eagles are gonna start circling that thing.”

Despite Rogaine, Propecia, Monasta and plugs, the rug trade is busier than ever, with the non-surgical hair-enhancement market clocking in at about $500 million a year. New York City, sometimes referred to within the biz as the Big Toupee, accounts for one-fifth of that pie. Mr. Paris said his shop has done over a million for two years running, with a client base of about 4,200—though that’s including his lady clients.

If you suspect a little something is going on, it probably is. Google it. Ben Affleck, Matthew McConaughey. Ding. Ding. What’s Ashton Kutcher hiding under that exquisitely tousled but eternally swept forward mop?

“John Travolta, my God, he looks like Bela Lugosi with that crown on his head,” Mr. Paris quipped.

How does the big show go down with that thing on?

“It’s the first question men ask when they come in here,” Mr. Paris said. “They say, ‘Can I sleep in it?’ What they mean is, ‘Can I fuck in it?’” Dammit, man, you can swim in it!

Mr. Orszag appears to be a fan of a certain bonding (“medical adhesive” is the preferred description) technique. “It’s just not right,” Mr. Paris said. “There isn’t a person living who doesn’t want to put something on and never take it off. But all I can say is that it’s like wearing the same underwear for a month. First of all, they bond it in a perimeter, and when you shower, because you can’t take it off and it’s bonded, the soap residue, the soap stuff goes through the lace and gets trapped by the bonding that’s all the way around.” Add perspiration to the mix: “You’ll smell like third base after the third week. Excuse the expression. It’s a sanitary situation.”

Mr. Paris prefers the clip. “Look how simple it would be to take on and take off just by doing this.” He unsnapped and set his own ever-so-delicate hair Frisbee on his desk. Amazing. “The secret to the most natural-looking hair system: If you can’t read a newspaper through it—that’s how thin it should be.

With mass-manufactured wigs, you wind up looking like the Fonz. “You’re like, ‘Whoa, what happened? That’s way too much hair.’ So you tell the guy to thin it out. He tells his barber, ‘Please thin it out.’ Now you’ve made long hairs and short hairs. You’re fine if you’re in a controlled atmosphere, but when you go out into the wind, the long ones blow up and you don’t feel it. The short ones come up. The short ones act like the support beams on a house. So you go into a restaurant with your wife and you say, ‘Order me a drink while I go to the toilet and see what the wind did to me.’ So now your whole world revolves around how much hair spray you’ve got to use the next day.” Also, nobody’s hair is one solid color, and so you need highlights, low lights to make it look natural. “Half of these idiots, it’s like trying to wear somebody else’s eyeglasses or dentures because they buy them ready-made and not custom-made.”

BEFORE HE OPENED up his own shop, Mr. Paris used to go around on behalf of the House of Revlon educating women on how to wear their wigs, what makeup to use, etc. Before that, he was an award-winning hairdresser. The other day, one of his secretaries found a Polaroid showing a 19-year-old Joey Paris holding a trophy: first prize out of all the barbers in Brooklyn.

“It was not a manly profession,” he said.

Mr. Paris grew up Joseph Guarnera in Bensonhurst. His mother worked in a coat factory. Dad was a butcher. Didn’t talk to his son for two years after his decision to take up the shears instead of the knife. “There were more gays who evolved to be hairdressers in those days than straight people. Now it’s whoever, whatever you want to be whether you’re gay or straight, shirt and tie, collars and cuffs. It doesn’t matter.”

Joey didn’t graduate high school. Nowadays, he listens to his surgeon clients whine when he’s carving out a mold: “‘I went to school for eight years and you’re cutting paper dolls and charging me $3,600 for a hairpiece.’”

Mr. Paris’ passion might have something to do with his suffering alopecia areata, which means spotted baldness—as opposed to totalis, which means you’re screwed—since age 14. The doctors told him it was stress.

At the International Beauty Show, an executive from Clairol offered him a job, on the condition that he change his name. He traveled around to various department stores across the country teaching the beauty technicians how to hide a wig. “Betty White. Marlo Thomas. Miss Sweden. They would get a celebrity to draw the women into the store. “

Soon Glendy Company, a wig wholesaler, came a-sniffin’, with the promise of a Thunderbird and fancy hotels.

“I would go around teaching people who would open up franchises and wanted to know how to cut and style wigs; I would educate them. I then finally said, ‘Why am I educating them?’”

He opened his own salon on Queens Boulevard, and soon expanded into Newark and surrounding areas. After several years, he ceased with the women’s wigs, opening a salon across from Bloomingdale’s in 1972.

At that time, he was also breaking into the motion picture union. “I was doing Naked City. There was only one woman on the set. So I would do her in like a half-hour, and meanwhile I would do nothing all day long. So I would get these young actors coming in wearing hairpieces and I’d say, ‘My God. You’ve got enough hair in there for three people. Let me cut it down.’”

In the late ’70s, he was working for the House of Revlon and doing Perry Como specials. “Once I got into the union, Mr. Sinatra asked me to do his last movie, which was called The First Deadly Sin. So I get there and I’m doing Faye Dunaway’s hair, and he walks in with an entourage and says, ‘What are you doing with her, Joe? You’re with me. Hire somebody else to take care of her.’ I said, ‘Yes, sir.’ The first day of the movie, he said, ‘Joe, I’m tired of spraying my head with the powder. I had the hair transplants. I want you to make me a hairpiece.’

Frank Sinatra had blessed Mr. Paris’ life for a long time. “I was always a fan of his growing up,” he said. “I had his albums all over my basement.”

They became friends after meeting at a party thrown by Mr. Sinatra’s bodyguard, Jilly Rizzo.

“They’ve got Tito Puente wailing away. Our table is right next to the band. Life magazine is there. The astronauts are sitting at the table. I’m sitting there with my 18-year-old wife.” Mr. Paris was 20, maybe 22. “Jilly says, ‘Grab my wife and follow me in five minutes,’ because the band was so loud. I didn’t know that they had a code. Sinatra says, ‘I think it’s going to rain,’ and they both get up. That was the cue for them to leave, everybody at the table. He said, ‘Joe, follow me in five minutes.’” They went up to some rich guy’s apartment with a pool table and a Jacuzzi in his bedroom. “I’ve never seen things like that. Now it’s like 3 or 4 o’clock in the morning. My wife, her head was hitting the table. She was falling asleep. I said, ‘Jilly, I have to go.’ He said, ‘Take my wife with you,’ in a full-length Chinchilla coat. A diamond the size of a flashlight. He says, ‘Keep an eye on my wife downstairs with your wife and I’ll be down in a minute,’ So I’m running my keys through the thing and the girls are talking and all of a sudden the doors open and I see the bluest eyes I’ve ever seen, my idol, face to face. No voice came out. I just went, ‘Frank Sinatra,’ in total awe. He said, ‘This is the best Sicilian you’re ever going to meet, Frank. Say hello to Joey Paris.’ ‘Hiya, Joey.’ We got in a cab, went home. ‘I’ll see you tomorrow, Joey.’ I was like, ‘What time, where?’ I would’ve been anywhere he wanted me to be. I went to London with him. I went to Sweden. I went to Ireland with him.”

IT WAS IN the steam room at the Sands hotel that he discovered he’d made it into Sinatra’s inner circle. Frank was staying at the hotel and randomly decided, as was his way, that he would own the place for the next two weeks. “No strangers!’”

“Jilly said to me, ‘Come on down. We shave. We have chicken soup down there until Frank is ready to go on.’ So it was just a jam session, chit chat. But when Sinatra looks at the owner and says, ‘I thought that I told you I want this place for the next two weeks. Who are those two guys under the sheets?’ ‘Oh, Mr. Sinatra, those are the Righteous Brothers.’ ‘Rights brothers, wrong brothers, get them the fuck out of here.’ I turned to Jilly and I said, ‘Hey, I’ll see you later,’ and I’m ready to leave. He said, ‘Where you going, Joey?’”

After First Deadly Sin, he started working with Mr. Sinatra privately. It would be: “‘Joe, I’m having dinner with the Rockefellers tonight.’ So after the set he would go home, take a shower and then I would put the piece [back] on for him.”

The timing couldn’t have been better. The ’80s were the gilded decade of the toupee trade.

The boom years were followed by a tremendous bust, says Andrew Wright, CEO of one the country’s biggest wholesalers of prefabricated … “hair grafts, please, not hairpiece.” He spoke on the condition that I not mention the name of his company, which is based out of Fort Lauderdale. Gone are the days of brand-name recognition, let alone acknowledging the wig’s legitimate right to exist. The hairpiece took a bath in the early ’90s. It was the dawn of a new absolutism: Two options: Own it à la Bruce Willis in Die Hard, or shave it. Anything in between is the province of pathetic freaks, sexual deviants and—perish the thought!—extremely vain men. The catalyst was the advent of the shave-it option. “The Michael Jordan moment or whatever you want to call it,” Mr. Wright said.

What about transplants? Mr. Paris has tried them, but doesn’t recommend.

“They went too deep and they hit a nerve. It’s a little bee sting. The bee that stung me was the size of Cleveland. I went”—he moaned—“from the pain. If my girlfriend hadn’t been standing by there, I would’ve screamed, but I just pressed my head against the table and bit the bullet. It’s a band-aid on a hemorrhage.”

His is a finer art.

“When you raise your eyebrows and frown, that actually tells you where your hairline used to be. That’s what we trace, and we put two small laced pieces, made out of angora. It’s very simple. You don’t have to shave your whole head to get the look that you want.”

He has nothing but scorn for the ready-made rugs. “Like, ‘Give me one 7 by 9, one 7 by 10.’ They pull it out of a box and tell the guy ‘ready in three weeks.’ That’s what they’re getting away with. There was actually a Web site, hairclubsucks.com. Just horrible how they’re ripping people off. But a word to the wise is that if they took a measurement of your head, when you go to pick up your hairpiece, place the measurement, the custom measurement that they took, and put it into the hairpiece. It better be like a fingerprint. If not, you know that they’re selling you a stock item.”

Mr. Paris understands that his trade has a certain … stigma. “Let’s put it to you this way: If I said to you ‘toupee,’ what kind of image do you conjure up? Heil Hitler, right? Something that you can spot right away.”

He did not do Hitler’s toupee. He did do King Hassan II of Morocco and Chris Meloni of Law and Order.

Mr. Paris plunked his own soft and flimsy unit into my hand.

“If you want to, I think a little eyebrow in each corner would work well on,” he said, leaning in for a closer look. Why not, no one will notice, just look at his own seamless situation. “Does it look like a hairpiece? If it does you should tell me. … There isn’t a guy who literally doesn’t want a full head of hair. He’s not looking to be a George Clooney. Not at all. He just wants to be himself.”

editorial@observer.com

But the children of the Upper East Side still have Jack Dorrian to comfort them when the newness becomes too much to bear. They know very well that he has been there, at his bar, Dorrian’s Red Hand on 84th and Second Avenue, from 10 a.m. and 5 p.m., forever.

“You pay with your body,” Jack likes to say. He is 75. You can usually find him at his table playing spades, or in his office doing the books and smoking a cigar, or roaming around fiddling with place settings, watching. The bar business is like any other business. If you want to survive: “You gotta be there.”

“Everyone knows Dorrian’s is like a rite of passage for anyone who grew up on the Upper East Side,” society writer Peter Davis told me. A Buckley boy, he got drunk for the first time there, had his first kiss there, with a Hewitt girl (they would do things that a Spence girl wouldn’t). “But lately there’s been an resurgence among the whole crowd of kids in their 30s.”

Is it the karaoke on Tuesday nights, when Topper Mortimer does a great version of the Boz Scaggs tune “Lido Shuffle”?

Dorrian’s had always been the designated place to go during holidays or when prep schools and colleges have breaks. But now it seems like there’s a whole scene there, that makes the trademark preppy co-ed bar the perfect place for the old boys—and girls, too!—to congregate, without feeling like geezers paying a return visit to their Ivy League frat house.

“I think part of why it’s so hot right now is the recession and people not having cash and it being not a $20 cab ride away downtown,” said sociable gal Anisha Lakhani. “And then coupled with things like, you know, this is not Rose Bar where you have to get past someone or like ‘velvet ropes’, if you have an ID you can get in, basically. …”

“It’s like opposite of the Boom Boom Room, which is like the new Studio 54,” said Mr. Davis. “The Boom Boom Room is the hierarchy”—every time he goes there he passes by a long, tragic line of plebes waiting to get to pay $25 for a drink—“and Dorrian’s is the democracy.”

JACK HAS A square head, with a handsome, wrinkly face and an impressive head of white hair. If you don’t act like a wise guy, he’ll tell you how things work. Shut up about the Preppie Killer, that was a fluke. He’s not terribly interested in talking about how for nine years back in the ’80s they served free dinner to the homeless on Monday nights either—they apparently started stealing the silverware and showing up in cabs and calling to ask what was on the menu.

His is the red-checkered four-top in the back corner; if he’s not in it, a deck of blue playing cards kept right with a rubber band will be marking his seat. It faces the door and has a view to the mirror that reflects on the bathrooms. You think that’s a coincidence? Jack’s smoking in Romeo & Juliet’s now. His horse Don’t Blame the Cat races on Sunday, which means he’ll have to go to Saturday mass at 5.  Business has remained remarkably steady this last year, yes. Someone recently informed him that Dorrian’s sells more Jägermeister than any other bar on the East Coast.

“The thing about the bar business is, you’re only as good as your last burger,” he said. The other thing is, you don’t give up your trade secrets.

Nothing escapes the watery baby-blue eyes of Jack Dorrian, and between his eight children, all of whom he put through private school—“What, am I gonna put ’em in with the dopes?!”—he can keep a pretty good bead on who’s who and what his value is beyond just blood.

“Water seeks its own level” has been Mr. Dorrian’s business philosophy for 47 years, one he inherited from his father, Red, who ran a number of bars, including an incredibly successful gay speakeasy called the Wrinkle Room.

Jack’s really smart about choosing his bartenders. Take Alex Brown, who’s been there for like a year now and does Thursdays. His brother’s Cabell. Cabell always goes out with John de Neufville. John de Neufville is dating Genevieve who is, like, a Vogue girl. John de Neufville is also best friends with Topper. Cabell’s wife is Vanessa Kilbert Brown. Vanessa’s best friends with Lauren Santo Domingo, who also works at Vogue. So on a Thursday night, you’re getting that whole group. That said, Alex couldn’t be a slower bartender. You just stand there, and you’re like, what the fuck? Totally nice guy, totally inept. 

Monday night is Callum, Callum McLaughlin. You know Callum, right? Awesome, sweet guy. Brother of Gavin McLaughlin and Andrew McLaughlin. Grew up in Far Hills, New Jersey. Bam! So now you understand, the whole Far Hills contingent’s gonna come. Though Annabel Vartanian doesn’t come very much, whatever that means.

But Jack says an even more important guy in the saloon business is not the bartender but the porter. “Unless he cleans the place up for the next day, if someone gets sick or the toilet is clogged or there’s a party, if he doesn’t clean up the place—that’s the most important guy you have in the bar business.”

Jack got the place a week before Christmas, 1959. It came with Christmas decorations and wrapping paper behind the cash register. When Jack went to take down the wrapping paper, he discovered someone had left two bullet holes in the mirror. 

“So this was a rough neighborhood at that time,” he said.

Turns out there were two different factions in the neighborhood warring with each other. Two guys were looking to shoot a guy, and they called him on the telephone down York Avenue, and he went to the telephone booth that was in the window. While he was in the window talking to them, they shot at him from across the street, through the window. Jack doesn’t remember whether they were gangsters.

“Whatever they were, there were two groups, and I wasn’t from this neighborhood. I was from the Bronx. These two groups didn’t like each other and I had this bar. This bar wasn’t like it is now.”

Now it’s all cornball. Built almost like a house. Brick and wood, a nice real fireplace. Old black-and-white photographs on the walls: of the good old days, friends, family, some horses Jack ran. There are no hookers in here. No drug deals in here. No gambling.

Back then, you didn’t have the back room. You didn’t have the outdoor cafe, where Paul Johnson-Calderon likes to come and pretend to play backgammon in the summer. Once a guy pulled a switchblade on Jack. “It was tough.”

When he bought the lease, there were two mortgages on it and it didn’t do any business. Five hundred a week, seven days. Eighteen dollars in the daytime and $42 in the nighttime and you were open from 8 in the morning until 4 in the morning. He was 30. Bartender till 6, then he’d walk the four steps over to the kitchen and get to skilleting.

“During the daytime, if things were slow, I’d be cutting the tables and making meatloaf and making hamburgers and that kind of stuff, a bunch of French fries. At 6 o’clock, the night bartender came in and he went there, and I went to be a cook until 12 o’clock at night. Then I went home and I was back here at 8 o’clock in the morning.

It was the same for Jack’s father, a college-trained electrical engineer, who came over from Belfast in the ’20s. Six months later, he was a bartender in a speakeasy. But in that generational transfer, the son moved the ball up the field: In 1977, Jack Dorrian bought the entire building, including the 16 apartment units above, in one of which Jack’s father lived out the last years of his life.

I asked if his father was his best friend.

He gave me the cockeye. “My wife is my best friend,” he said. “By far.”

His father’s name was James, but everyone called him Red. Then he had his own speakeasy called the Red Wheel or some such on 51st Street, two houses off of Third Avenue. Then he had a bar downtown on 13th Street.

When Pete Hamill, whose dad was lifelong pals with Red, asked his mother if Red Dorrian ran a gay bar during Prohibition, she said, “‘Of course not. He’s a Catholic,’” Mr. Hamill told me. “But apparently that’s what went on.”

“They called it the Wrinkle Room,” Jack said. “What happened was my dad was working at a bar downtown and a lot of older gentlemen who were gay started coming in there, so it became a gay bar. But it wasn’t like it is now. Back then no one talked about it. They weren’t faggots, they were gay.”

Though it does seem that Rock Hudson was a bit of a faggot. “They had banned him ’cause he would go in there and hustle people.”

I asked him if he meant he was a pool shark.

“What?! No, he would hustle people. He’d go in there and go home with guys for money."

FROM THE START, Jack understood very well that the key to success was to re-create that poor man’s living room idea, just only with rich brats instead. Burgers were 50 cents, a beer was three dimes and a nickel, and a cab back to his home on 71st was three quarters, make it a dollar and the cabbie was happy.

“Yorkville had been a working-class German-Irish ghetto. There were three other German bars on the block. When you walked down 86th Street, you had the Berlin Bar, the Lorelei. The Bismarck. From Third Avenue to First Avenue you had 25 German restaurants. Then they used to have across the street the Gay Piano, the Blue Danube. In 1939 there was a guy up here who had a milk company, and these people were selling milk and they used to come over and collect money before the war started. Then over here you used to have a stand put out, and they would have guys come dressed as Nazis and they’d start talking about the Nazis. Then you had people who were from Europe who came over after the war; they were Jewish and they would come in and fight with these people. The cops would come in. Across the street there were two bars, little places that had Jägermeister behind the bar The would be a guy with a bottle of Jägermeister and some pickled pigs knuckles. Apartments were going $40, $50, $70, the rents. They were all cold-water flats. … What? Cold-water flats, you don’t know cold-water flats?

“There were 16 apartments upstairs and the most anyone was paying was I think $100. So it was all families and working folks.” Back then it was commonplace for bars to offer both hookers and gambling. Not Jack; he was in it for hell and high water.

Things started looking up when the Australian newspaper folks, many of whom lived in those cold-water flats upstairs, made Dorrian’s their clubhouse. There were newspaper offices up in the United Nations and then they had the Herald Tribune.

“So we had a big rugby, newspaper people here. But it was altogether different, the newspaper people, than they are today. They had some backbone. They more or less were men. Straight guys.” He looked me in the eyes. “They didn’t want to hurt you.” Well, no, they were part of the club.

“That’s how we started off and try to keep that going since that time. We like to know our customers, talk to our customers, and we like to give value for the money.”

That there is harder said than done. Not the keeping up with a good burger’s worth in gold. Give it a number: Ten bucks for the classic with cheese. But in the bar business, you’re only as strong as you are with your customers. It’s the making-the-water-seek-the-right-level that’s tricky.

It got trickier after the baby boom generation took over and young people start moving out here from places like California.

“What I mean by the right people is people who are not going to cause any trouble,” Jack said. “So if you have a group of college people in here, that’s what you’re going to get. The kids who are not college kids, they figure they’re lacking education, so they find some place else. So that’s what we get. If the girls are dressed accordingly, the other girls won’t come in because they think they’re not dressed like the other girls,” he explained.

Yeah, there’s a dress code. “It’s not tuxedos but it’s not tank tops. It’s not cutaway.”

I asked Jack how he felt about big, baggy pants. He gave me the stink eye. “What are you kidding?"

JACK DECIDED TO give Peter Smith, 27, a shot with his karaoke night in May ’08. He was born uptown but became downtown. “I feel like the hipsters have Black and White; the punk kids have Lit; and, yeah, Dorrian’s is the preppy bar,” Mr. Smith said. “But the great thing about the karaoke night is, I feel like it brought a lot of different types of people together.”

His band, the Shooting Gallery, would sometimes come up wearing their colors, leather jackets with peace symbols on the shoulders, and perform songs. To be clear, they are not a biker gang. Jack says he was never part of any gang. Mumble mumble. He went to All Saints High School and some local college. He was horribly dyslexic and had terrible grades. He flunked out of law school and decided to go into a legitimate business.

“We never had, to my knowledge, girls of the evening or gambling or drugs. We’ve always had people call and say they’re happy their sons are here because at least they know where they are.” (Even if he is in the cellar having a quickie with a floozy while his steady was waiting in line to use the bathroom, as one proud patron relayed.) “We make enough money that we try to keep it legit and we don’t need anything else.”

Parents are part of it. Socialite Annie Churchill looks back fondly on the day she got the shoulder tap. “One night, while I was home from boarding school for the weekend and staying with my father in the West Village, I went out to Dorrian’s and was told that my curfew was 1 a.m. Around 2 a.m., I got a tap on my shoulder from my friend Michael Dorrian, who said that I had a phone call. I got on the phone at the front desk by the window, and it was my father. He said, ‘Come home right now, or I’ll call the police.’”

Mr. Smith says that Dorrian’s has gotten serious about ID’s. Jack thinks the whole country’s going to hell and that nobody wants to be held accountable for anything, including their children.

There’s no shame in get tossed from the joint. “I think everyone I know has been a little too drunk at Dorrian’s,” said Mr. Johnson-Calderon. “It’s when the tykes are having trouble getting into the bar is when parents might want to avert the eyes.

“You’re standing on the door, and we have a guy on the door, and people open the door, and you’re standing there and they see and go, ‘Well, the guy’s drunk or he’s not dressed right’—or there’s seven or eight guys and he knows they’re going to be trouble,” Jack said. “So, the guy says, ‘We’re closing up,’ or, ‘We have too many guys in here.’ When you put too many bulls in a pen and there are no cows, they’re going to start going at each other. Am I right or wrong? So the guy on the door will say, ‘No, we’re closing up now. We have too many guys now.’ Then someone will say, ‘You’re a nigger.’ And you’re standing there with him. You feel worse for the guy than the black guy does. I mean, it’s really embarrassing.

“In the old days they used to just get out of here,” he continued. “Same with the police department. I remember in the old days, when we were in the neighborhood and there was any trouble, the cop’d hit you over the ears with the nightstick and you went home. You never told your mother. You told your mother that a cop did that there, and she hit you. You went to school and the teacher yelled at you. Your mother was horrified and she made you stay in. Today they go to the school and they say, ‘What are you hitting my children for? What are you punishing them for?’ It’s just ridiculous. They don’t want to take any responsibility.

“The clientele we have today is what we had. Nothing different except the names. It’s the same people that come along with the same problems.

“What are they? I didn’t graduate from school. I lost my job. I want to go to medical school. I want to be a lawyer. I want to be in the movies. Everything. I want to be a writer. It’s all the same thing. People come to New York, and if they don’t walk slowly after six months, they go back to where they came from. The hotshot goes back to where they come from.”

editorial@observer.com

“I can barely stand,” Seth said, swaying innocently on the soggy sidewalk. (Seth’s a gentleman and asked that I change the names and obscure certain details in unfurling the horrors that so thoroughly furled him that night, in order to protect the honor of a woman.) He was 24 at the time, a magazine writer.

Joel said, “O.K., I think he needs to go home.”

Dana, who was 29, said, “Let’s go get another drink!”

“I wanna go home,” Seth warbled.

“O.K., I’ll take him home,” Dana said.

Joel gave Seth a “WTF?” look and said, “I’ll take him home.”

“Don’t worry about it,” Dana said, hailing a cab and then bundling Seth inside.

“I woke up with a condom still on my dick,” he told me.

A few months later, Seth found himself watching helplessly late one night as Dana picked off one of his pals much the same way she had him: The fellow was babbling, stumbling drunk, and Dana chirped: “I’m heading the same way, let’s share a cab!” Another poor shmo who hosted an after-party at his pad one night to enjoy a little group reefer session suddenly found himself alone, except for Dana. Game over.  

“She knows what she’s doing,” Seth told me.

MUCH HAS BEEN made of the so-called cougar, the older dame, early 40s on up, who has developed a taste for the younger man-beast. Dana’s hunting methods and psychology bear no resemblance to the cougar. As Seth aptly points out, “A cougar would fuck and then leave and not feel bad.”

Instead, Seth awoke to Dana’s limpid eyes, followed by an awkward kiss in broad daylight as the two parted ways on the street. The cheetah stays the night.

The Dana “type” was familiar to me. There was a girl I knew in L.A. who fit the bill. She’d sunk her teeth into at least 20 percent of her lopsidedly male friend group. All you had to do was watch the faces when she approached to know which ones she’d had her way with.

Good God, I thought, how many of my fellow men are at risk at this very moment?!

I thought the same on a recent night here in New York, when my wife showed me a “funny” text one of her girlfriends sent her inquiring what she was up to—we were in a car, heading home—and sniggering that she herself was “out on the prowl.” I immediately thought of the widely held view that single women are keen to get their paws on a hunk of man to hunker down with for the winter months. I looked out the car window—it was raining. A cold, insinuating rain. The conditions were perfect for a cheetah to a strike.

The cheetah is most often a just-one-of-the-guys girl. That’s her cover. In nature, a cheetah will lurk in the high grass and use her spots as camouflage.

I called up an accomplished and self-described cougar named Angela, who works in TV production, to see if I was out on a wild limb. “Well, she’s not a puma,” Angela told me. A puma, Angela further explained, is a woman in her late 20s to early 30s who preys on “the babies—guys who are like 21.” Angela said she wants to write a sex memoir, with any luck before she enters the saber-toothed stage.

She noted that her friend K.C. was a cheetah. Recently out of a relationship, K.C. has discovered that getting a man was no longer as easy as it once was. “It seems like whenever she can, she winds up going home with the drunkest guy in the bar,” said Angela. “Of course, in the back of her mind she’s hoping that her pussy’s still good enough to keep him.”  

A.J. DAULERIO, who runs the sports news website Deadspin.com, first put his finger on a phenomenon he dubbed “cock loitering” back in 2005.

“A cock loiterer is typically a girl who has recently come out of a relationship that she’s been in for a long time, and she suddenly realizes that getting laid is not as easy as it once was,” Mr. Daulerio explained. He noted that the cheetah hunts alone, and prefers gatherings where she can blend into the crowd until the quarry grow weak and sloppy. “You know, she’s the type who’ll come out to the sports bar for Sunday football and then, whereas most people will leave after the 12 o’clock game ends, she’ll stick around for the 4 o’clock game,” he said.

He added that the cheetah was not necessarily unattractive but that for some reason or another, she was not aware of her attractiveness. That said, the cheetah he had in mind was notorious for looking dreadful without her makeup on and, as with Dana, working her way through his friend group.

New-media mogul and man-about-town Lockhart Steele is part of that friend group. He rightly pointed out that the cheetah isn’t just looking for whatever carcass she can haul out of the bar—incidentally, cheetahs are one of the few animals that will not eat carrion—but rather it is about women past the first flush of youth wanting to date or at least fuck “above their station.”

“Women in New York tend to be at a huge disadvantage,” said John Carney, of Businessinsider.com and another cheetah victim, via Gchat. “Many moved here from elsewhere, severing the kind of social bonds that ordinarily would provide introductions to potential mates. The cheetah is an ill-conceived attempt to overcome this situation.” He added later: “It is tragic. They should put a warning in cabs, like they used to about seat belts and remembering to collect your belongings: ‘This random hook-up will not likely lead to a relationship. Please exit the cab with all your dignity.’”

The troubling thing about the cheetah is that it’s a lose-lose for both predator and prey. Both her Auntie Cougar and Cousin Puma have a certain dignity. They’re out there shakin’ it up, slaying dudes and taking names. Not so the cheetah, who hopes that her victim will find something in her searching eyes when he rolls over the next morning, and will try to subtly guilt him into another round next time they meet: “Hey, where’ve you been? I haven’t seen you in so long.”

Angela would like to do the cheetahs of the world a favor: “Heed my warning: You’re never going to get a boyfriend or a husband this way. Men like to chase. The only man you’ll ever get to stick around by being a cheetah is going to be a total pussy.”

editorial@observer.com

At the Last Crack Hipster’s corner bodega, the code word is “Casaban.” You’re handed a brown paper bag containing the glass tube with a tiny bunched-up ball of steel wool at one end, and a little lighter. It costs $2.50. (A can of Coca-Cola is 75 cents.)

For a moment a few years ago, among the downtown “edgy” set, crack was hip. At least as an idea: “Crack is Back” was the logo on downtown curator A-ron’s $60 T-shirts. No one ever really did it. The Sun reported back in 2005 that Kate Moss had done crack; but the Last Crack Hipster says she never really did crack--wasn’t a “crackhead.” For the Lower East Side artists, it was enough that Dash Snow smoked it and took lots pictures of it. Now he’s dead. The Last Crack Hipster says he’s got mad respect for Dash Snow.

The Last Crack Hipster wants me to keep mum about most of the personal stuff. He’s around 30 and a longtime member of a graffiti collective.  The Last Crack Hipster looks a bit like a raccoon, but not in a bad way. He’s a shower man, prefers the spray to the soak, has an iPhone and a serious girlfriend. Grew up out West. His parents aren’t millionaires, but if he’s in a tight spot, they’ll help him out. His apartment is littered with art books and kitty litter. A high-school doodler and onetime community college dabbler, he never lost the fascination with pop culture that ate his homework; his eyes are still wide. They’re bulging now, as he tears open a fresh Chore Boy. People will call it Brillo, but it’s Chore Boy, the one with the little boy on it. You have to get the copper-scrubbing pad because the other one is aluminum and it’s terrible for you. It burns your brain. So once you’ve got the copper-scrubbing pad, you pinch off about a gumdrop’s worth. You hold this over a flame, burn it really good, because there’s like a layer of cleaning product—well, whatever it is, it burns green at first. Wait until it turns black. If you don’t, you can taste some sort of chemical, probably cancerous.

Are we having fun yet?

You also need something to push the burnt copper into the glass tube. A chopstick will do. Push the Chore Boy down a little bit, to allow for enough room at the top to put the crumbs of crack on. Crack comes in a baggie the size of your fingernail with the yellow rocks in it. Twenty bucks. It’s ready to smoke. Ready rock. Hard. When you buy it, you say, “I want Hard.” A lot of crackheads on the street melt all their crack down into the Chore Boy and it looks green. If they get frisked by a cop, it’s just paraphernalia.

When being smoked, crack doesn’t have a strong smell; it’s like a sulfuric smell but with a sweetness, and the smell goes away really quick. Your house isn’t going to smell like crack, even if you don’t have one of those discreet cardboard kitty shitboxes lying around.   

When you’re smoking crack, ideally you want to keep the flame on the crack and away from the Chore Boy: You want the rock to heat up and cook down into it. It starts to melt and then it slides down and that’s when you go boom and level it out so it stays right at the screen. It’s right there bubbling and you’re not sucking like a cigarette or a joint; you’re basically like inhaling as little as you can. You just want to direct the flow into your mouth; you don’t want to suck the liquid down. Once the burning crack passes through the Chore Boy, it smokes as it cools. That’s the smoke that you want. Most people don’t seem to get that. It looks like the crack is gone, but you can kind of see it in there, in the Chore Boy, ideally it sits there and bubbles. The brown juice that drips down and looks like a film of motor oil on the side of the glass is the crack rock’s sweet nectar. People call it the Caviar. Taking someone else’s Caviar hit is uncool. 

THE LAST CRACK Hipster insists that, as negatively hyped as it is, crack is not really that big of a deal compared to a lot of things. Granted, it’s highly addictive, and granted, it destroys people’s lives. Lots of times, a person will hit it and not feel anything much and be like, What’s the big deal? You hit again and again and again for a night. But the next day you don’t necessarily want crack again.

The media got it a bit wrong, he said. It’s not quite the bogeyman that they make it out to be. People who snuffled mountains of coke for years, the instant someone mentions crack, they freak out, panic, run the other way.

Crack Hipsters were a reaction to their parents’ nudge-nudge, upper-income-bracket embrace of cocaine. The Last Crack Hipster likes to point to the 1990s. The year that Nevermind dropped, in September 1991. A week or two later, the world went gaga for Michael Jackson’s album Dangerous, with the hit single, “Black or White.” But by January, Nirvana was ruling the charts. David Geffen had signed Sonic Youth. They didn’t have to release anything on any schedule. But Geffen knew if Sonic Youth signed, the best new grunge bands would follow.

Geffen bet right. Kurt Cobain didn’t want to go on Geffen’s label; Sonic Youth leader’s, Thurston Moore, talked him into it, so they could go on tour together. The kids ate it up. Everything had been getting too phony and theatrical. They wanted something real. The grunge scene was real. Heroin somehow went along for the ride, as a “real drug.”  But how did crack snake its way into pop culture?

In 1994 Kurt Cobain blew his brains out; meanwhile, a couple of fellows in Quebec start Vice magazine, a significant force in the mash-up of graffiti artists, skaters, DJs, male models, slam poets, drug dealers, party promoters, T-shirt designers. Maybe you just worked the cash register at Supreme, but you could be a “lifestyle artist.” You could be an accountant by trade so long as you wore it right. You want to do the ’80s rocker thing with the long hair and the tats, or how about go the exquisitely sloppy route, all Middle America with the wifebeater and the potbelly? Do it.

There were also the hard-core pioneers: graffiti writers from Sherman Oaks who would slice your face open, or guys who declared, I’ll fuckin’ smooch a dude, whatever, yo. Whatever the pose, do it right and you can collect your prize: You’re an artist now, the superstar of your own show. If you’re lucky, your picture might wind up in the Do’s and Don’ts of Vice, alongside the skinny Puerto Rican kid with no teeth, neon full-shutter sunglasses, an oversize pristine baseball cap with the bill flipped up, taking a leak on a street corner in broad daylight. 

But by the early 2000s, the cycle of cynicism that began in the ’90s caught up to the Vice generation. Heiress Paris Hilton got fucked from behind on camera, the ultimate star of her own show. But the purists still had a card to play: crack. A new lease on coolness, bohemian transgression, mystery.

The Summer of 2004, the cover of Vice magazine showed Pete Doherty hitting a crack pipe. A few months later he’s dating Ms. Moss, a cracked romance.

Oh dear God no. No, no—no way. Check this … It’s so … ha!

A powerful thought was rattling around the Last Crack Hipster’s brain. So check it out, the downtown hipsters were doing their thing, crack jumped the pond and burned up London; meanwhile, the hip-hoppers were gassing. In 2005, the rapper Juelz Santana came with the hit single “I Am Crack”:

Touch the coke, touch the pot, add the soda what you got ME!

I am what I am I be what I be and that you will see I AM CRACK

Santana was saying, “You think crack’s cool, here’s the recipe, tough guy, you will see.”

THE LAST CRACK Hipster had finished the Hard and was settling into Mad Scientist mode with the Soft and the spoon and the baking soda. Something about patience being the key, don’t rush it. Things were getting weird.

He suggested I call the coke dealer he says taught the Lower East Side set how to “cook”: that is, how to turn a bag of blow into a crack rock. The Chef’s clean-cut, L.A. born and raised. He spent three years milking the LES.

By early ’07, crack had begun its inevitable decline in the fickle world of fashionable downtown New York. (Some people didn’t get the memo; the original Crack Dork Amy Winehouse fixed that.) But in the days when Ms. Moss and Mr. Snow were doing the twist at his Tribeca studio, it wasn’t uncommon for the Chef to teach 10 or more “rich kids” how to cook, in a week. Lots of these youngsters didn’t have the dedication, patience or mental fortitude to create “the miracle of life;” they preferred to pay for the goods and the show. “I was known as the best chef around, so people would call me just to get me to come over and cook,” he told me. “But yeah, obviously, most of these kids were in it to be cool or whatever, lightweights. Except for those who weren’t, who eventually fell off.” It was usually dudes, but then there would be girls with the dudes and then sometimes the girls would start calling. The Chef feels pretty bad about what he did, says he saw a lot of good kids go bonkers, wind up in jail or the nuthouse. He may or may not still be in the game, but it’s been years since he trained any new chefs. He made a vow.

I pulled a big art book, Nest, from a nearby shelf: a beautifully bound volume documenting Mr. Snow and Dan Colen, the kings of the New New York School artist crew, creating one of their famous hamster nest experiences in an empty apartment. Here a photo of a naked pregnant babe teetering on top of a ladder, shreds of paper floating all around her; there a mangy red-eyed maniac grinning as he tinkles on the rising tide of paper and pillow stuffing. Ten pages of Nest is enough to make a man lunge for the crack pipe, or sledgehammer, whichever’s handy.

The Last Crack Hipster pushed an extra thumbtack into the blanket covering his window. He was getting the wah, wah, wahs. Basically, your adrenal glands are pumping and your fight-or-flight instinct kicks in and you become naturally fearful, maybe toward the police because of the drug’s illegality.

All of this is ending, donzo: Last week A-ron hosted a bring your own homemade ’zine party, open to anyone with a glue stick and a Kinko’s card. We’re on the cusp of something new. The Last Crack Hipster can feel it in his bones. These kids are coming up and technology is going to drive them hard. Insane. Everything that you do is just going to be out there. Look at Twitter: “I’m eating dessert.” 

The Last Crack Hipster finishes tacking the blanket in front of his window. Then he sits down, leans forward and lights his lighter. With a candle. No clicking noise, see? 

editorial@observer.com

This story was updated from an original version published Oct. 20, 2009.

Collecting went beyond cards and comic books. By 10, young Devon was dog-paddling in strange waters.

Mr. Gilroy described discovering “these old black spoons at like a yard sale or something. I remember that I polished them and found that they were like silver. They had all these little things on them. Some of them had chips from the different countries. I remember cleaning them, [being] obsessed with them and I had them rolled up in these towels and I had them stored in my closet. I’d put them there and I’d forget about them but then I’d find another one and it was almost like rediscovering it again because I’d be like, ‘Oh my God, I can’t believe that I have this one.’ And then it was organizing and cleaning them again. I had this idea that they were worth money.” 

Don’t feel too bad for the little
fella: By 11 he was on to obsessing over a landscaping business. After a year or so of saving, he got a mini-tractor, took the business townwide and was raking it in. That’s cool!

His mother, Mary Miscikoski, owned a small vintage clothing store. On weekends, his father, the legendary New York restaurant-nightclub operator Billy Gilroy—who began as the manager of Nell’s and went on to operate and co-own Lucky Strike, the Match restaurants, Employees Only and Macao—would take young Devon to flea markets to outfit his latest endeavors. The spoons say it all: The boy’s brain was wired to get stuck on a track and repeat.

At the age of 19, on a whim, he took a job as a fry cook at the Grey Dog cafe and discovered that something about the combination of chaos, camaraderie and the ever-elusive quest for perfection in a working kitchen appealed to him. Were it not for his fondness for routine, Devon Gilroy might have missed his calling. 

“I very much like things to go a certain way,” he said, “and sometimes when that pattern is broken—initially it drove me really crazy, but what cooking taught me is that you have to really let go of control. It’s not controlling every situation all the time but it’s controlling how you react to all those situations. So it has to be a very disciplined environment, because it can get very chaotic.” 

Now 25, Devon Gilroy is in the unusual position of being able to create his own controlled environment—outfitting his own kitchen, putting together a staff of about 25 people, designing his own menu—as head chef at the East Side Social Club on 51st Street, which is scheduled to open mid-November. The pressure is on. 

THE VESTIGES OF  an extreme personality are still there. Mr. Gilroy, whose torso and arms are covered in tattoos, has fixated on every element of the kitchen that falls under his domain: the kitchen, the menu, the staff. He’s earned the trust not only of his father, a notoriously no-nonsense animal-beast businessman, but also of deep-pocketed friends who came on as investors (including notorious tightwad photographer Patrick McMullan, model Eva Herzigova and set designer Happy Massy, who is helping with the old-school Italian décor).

“I didn’t invest before because I didn’t have the money,” said the artist Dirk Skreber, for whom Devon worked for as a personal chef. “Then later I have the money so I wrote the check.”

Mr. Skreber said that he particularly enjoyed Mr. Gilroy’s monkfish. Also that Devon was handsome, and that one time, “he cooked for us and then some girls were there, and then after he was with the girls and then we asked him to—oh, no, I shouldn’t.”  

His teenage years were a bit of a wash for Devon, who took an interest first in football, then in drugs. He was booted from the South Kent school and, after a year of military school, opted for the GED. He moved to the city and fell in with a wild skater crew. His dad got him a gig working at his pal David Barton’s gym. Mr. Barton’s wife, party promoter Susanne Barstch, employed him as eye candy at her gay parties. “That was pretty weird,” Devon said, noting that his tasks often included standing around on a stage near a guy in a head-to-toe leather suit. 

Devon said he had no clue what adventure with “the girls” Mr. Skreber was referring to, but that the opportunity to get paid experimenting on starving artists was a boon to his development as a chef. After putting in his time at the Grey Dog, which has a vast, diner-style menu—“eggs are actually one of the hardest foods to work with because they’re so delicate,” he said—Papa Gilroy allowed him to pick up some hours assisting in the opening of Employees Only. Once the restaurant was finished, his son inquired if he could take a low-level position in the kitchen.

“I was skeptical of the idea,” Bill Gilroy said. “It’s one thing being his father, but to be his boss is something different altogether.” 

BUT DEVON HAD already developed his own relationship with the chef there, who was open to the idea, and so Mr. Gilroy gave his blessing. Devon said the chef, who has since departed, like to hit the sauce and ran a sloppy, unnecessarily chaotic kitchen. Devon had himself gone cold turkey on the booze after he noticed his hangovers getting in the way of his mastery of the Grey Dog grill.

After a year at Employees Only, Mr. Gilroy fils decided to take an apprenticeship with David Waltuck at Chanterelle.

“David had a very subtle way of letting you know if something was good or bad,” Devon told me, over a cranberry juice at Macao, his father’s Chinese-themed restaurant in Tribeca. “He’d pick up a carrot that I had prepared and look at it, and then put it down.”

Eventually, the carrots started looking right and Mr. Waltuck hired Devon, who worked his way up to the top spot in the kitchen. Chanterelle is four stars and French: Great experience, but the young chef doesn’t feel he needs to make another cream sauce.

Next came an eight-month stint as the number two at A Voce, under Missy Robbins. It was there that Devon Gilroy discovered what he already knew: His heart belonged to Italian.

Indeed, it’s in his blood. Along with recipes Mr. Gilroy developed on his own, the East Side Social Club will feature some from his paternal great-grandmother Rosemary, who grew up in Naples (one of 12 children), like a striped bass with sage. Also, a distant uncle’s unparalleled fresh mozzarella. The restaurant is a family affair: Grace, who worked the Maritime Hotel for five years, is in charge of the front of the house, and his uncle Jimmy is managing the joint.  

Food is not the only realm where Mr. Gilroy’s Italian side expresses itself. “He’s definitely got game,” said Grace, who recently moved in with her brother across the street from the Social Club, which shares the ground floor of the Pod Hotel. Big sis reported a steady flow of model types going in and out of Devon’s room. She recently had a peek at his iPhone inbox. “There were all these texts like, ‘How about I cook you three course meal next week.’ Or, ‘Let me take you to this restaurant and show you about this.’ He definitely knows how to make a woman feel like she’s number one, even if she might be number three.”

Mr. Gilroy told me that if it weren’t for food, he actually wouldn’t like being around people. “I get bored easily,” he said of his love affair with womankind. “It’s like that obsessive side of me. If something’s not perfect, I lose interest.”

editorial@observer.com

“I would say that Doug ran a very energetic campaign,” said Steve Levin, who on Sept. 15 was elected to replace David Yassky as the councilman for District 33, which includes Williamsburg, Greenpoint, Brooklyn Heights and Boerum Hill.

“He brought a lot of passion, and when he entered the race, he helped shape the debate,” said Mr. Levin. In particular, he said Biv made other candidates address the issue of health care, and what can be done at the local level. In the final stretch, Biv rolled up his sleeves and turned his fight-the-power fist into a pointed you-dirty-bastard forefinger: He accused Mr. Levin of being a nursemaid to his “notorious” boss Assemblyman and Brooklyn Democratic Party overlord, Vito Lopez. On page 2 of The Brooklyn Independent Democrat, under the headline “Fiction vs. Fact”—all caps, black type, ensconced in a red banner—Mr. Levin is charged with standing by as Mr. Lopez screwed the little man, including the time he “deliberately tried to destroy a bill in the State Assembly that would have allowed adults who were victims of sex abuse as children to sue their molesters, because of a backroom deal between Lopez and the Catholic Church that gave Lopez control of the multimillion dollar Broadway Triangle development project.”

You’ve heard about all that, right?

Of the roughly 200,000 residents of District 33, around 18,000 voted. Mr. Levin got 5,199 of the votes; Jo Ann Simon came in fourth with 3,109. Evan Thies got 1915, Mr. Biviano placed sixth with 1,127, and someone called Ken Baer brought up the rear with 811.

Biv said he’d heard over and over from residents pushing Bugaboos up and down Montague Street—the Madison Avenue of Brooklyn Heights—that they didn’t give a shit about local politics. That is until they strolled passed the Biv’s store front, and were subjected to his “stroll poll.” Some version of the Stroll Poll has likely been instituted in the past but credit Biv with coining the phrase and shaking things up on Montague, which for whatever reason brings out the worst in Brooklyn Heights: Adults and senior citizens put on their boring cap and go mute, while youngsters armed with dripping ice cream cones—there are at least seven ice cream parlors on the three-block “center of commerce”—run rampant. The Stroll Poll changed all that.  

 “And check out Doug Biviano, one of the 33’s,” blared the Only The Blog Knows Brooklyn, “who did a 'stroll poll' asking pedestrians to write on a chalk board outside of his campaign office on Montague Street. Here’s what he found:

1. 37% — Healthcare   (57 votes)

2. 22% — Education   (33 votes)

3. 18% — Affordable Housing   (27 votes)

4. 15% — Parks & Playgrounds   (23 votes)

5. 8% — Corruption & Campaign Reform   (12 votes)”

A subsequent Biv poll put education as number one—education and health care were his two main issues. Meanwhile, Mr. Levin’s platform emphasized affordable housing, which brings us back to the “City Council what?” reaction by passersby. Mr. Biviano says that the kids were also fascinated by his homemade solar-power panel.

TO HEAR HIS mother tell it, when Doug was a kid he probably would have been plastering the roof with solar panels if they had been around.

“In kindergarten, they told me he was college material,” said Judy Biviano. “In kindergarten. He used to save his money and go out and buy computers and all these things, before anyone even knew what computers were. Seriously. He was in second or third grade when he bought his first computer.”

His parents split when he was young, and Doug spent summers in Brooklyn Heights with his dad. In high school and college he’d make extra cash doing odd jobs in the building, and developed a great respect for the job of being a super.

Of course, no job is all sweetness and light: “The big water bugs landin’ on you,” Biv told me with a laugh when I visited his office two days after Election Day. His spirit was not broken. He speaks with a Brooklyn–Long Island combo accent. “Fightin’ the garbage compactor, you know, when the sausage bag won’t break and you start fightin’ it and you fall into the garbage, you know, stuff like that. Watching the rats.

“One time I was walkin’ in the courtyard, and a rat came running by and ran right into the curb and kind of popped backwards and killed himself. The unbelievable luck of some of these rats.”

His mom claims that she never once heard him complain, ever. She also says that he wasn’t a nerd in high school, but he got straight A’s and was awarded a scholarship to Cornell. Math and science were his strong suits. He majored in civil engineering. He went on to get his master’s degree there.

Along the way, things got serious with Lee, whom he’d hooked up with in high school but then ran into again at a party one summer back in Long Island.

“They’re both the same way, those two,” said Mama Biviano, who is a conservative but said she would still vote for Doug, who likes to say he’s so progressive he’s conservative. “They’ll try anything. They were really daring when they first met. Jumpin’ out of airplanes and what not. I would be worried sick!”

“DOUG WAS ‘GREEN’ before I ever heard the term,” Lee Biviano begins her op-ed endorsing her husband in “Vol. 1 No.1” of the leaflet, which was distributed all over Brooklyn, and features various pictures of Biv in action: sweeping the stoop, wearing a construction hat, talking to Judge Robert Kerry, a 95-year-old man who lives at One Grace Court.

(Mr. Kerry confirmed to me that Biv was an excellent super and a man of great integrity and said that he used to stop by and have a drink with him some evening before his health deteriorated. He said that Mr. Biviano did not force his politics on anyone in the building. “Of course he didn’t. We would have fired him,” said Mr. Kerry. “I like Doug very much.”)

Congressman Dennis Kucinich also endorsed Mr. Biviano.

In her piece about her husband, Lee describes how when they were married, “Doug built a green sailboat for us and we sailed around the tropics for nine months.” The trip included a two-month stay at some sort of sailboat commune in the middle of the ocean, which Mr. Biviano said taught him a lot about what people can do when they work together.

Lee writes that it was with the birth of their first child that Doug became fixated on helping make the world a better place. He volunteered for a week in New Orleans in the aftermath of Hurricane Katrina. On two separate occasions, he tried to go down and be a part of the relief effort at ground zero. Lee and Judy both vouched that he’s the most dedicated father imaginable; in fact, Lee writes, “If he didn’t believe in our government, he’d be content to spend all day swimming off the side of our boat with our children.”

But he does believe. (He’s also a bit of a 9/11 conspiracy theorist, but whatever.)

“It was literally impossible to get him to go home at night,” said Wilson Karam, 28, a Ph.D. student in politics at the New School, who was Biv’s campaign manager. It was his third campaign, having previously volunteered for the DNC, and serving as deputy state director of Ohio for MoveOn.org.

“He’d be there some nights writing letters to the editor,” Mr. Karam said. “As a campaign manager it’s just like go to bed, keep your schedule, you’re not going to be able to get up to greet people in the subways in the morning.”

In the “What I’m hearing” section part of bivforbrooklyn.com, an impressively dynamic Web site, considering he designed it himself, Mr. Biviano describes his interactions with people on the street. There’s the conservative Catholic delivery man, the Brooklyn mommy blogger. His Open Door gallery series feature local artists. Currently on display is a series of portraits of mug shots of civil rights activists.

“We can pass the law for single payer,” he told me, looking around at the images of Martin Luther King Jr., Rosa Parks and others. “We can do that, and we can also pass the law to raise the revenue for it as well—we can do that. It’s within our charter. Um, but you need leadership to do that, that’s all you really need. And again, look right on my walls. And again this is just a reminder—in small cities, small towns all over this country, there were a few sparks, some courage, some leadership, and look what it did.

“Look where it got us. These aren’t even mayors, these are just ordinary people and a few reverends. And if it’s the right movement”—snapping his fingers—“the right spark, you can tap it. When people come together to solve problems, real problems, miracles can happen.”

editorial@observer.com

Several months later, he was waiting tables at French Roast on West 11th Street.

Since then, Mr. Mulholland has come a long way. He’s the founder and president of the Cain Leisure company, which operates four successful nightclubs: Cain Luxé, on West 27th; GoldBar on Broome; Cain at the Cove, on Paradise Island in the Bahamas; and his latest venture, the Surf Lodge, a nightclub and hotel that opened last year to a mix of fanfare and controversy on the relatively undeveloped shores of Montauk. 

“So you’ve never been wakeboarding before, mate?” Mr. Mulholland asked me as we boarded a speedboat in Sag Harbor on a recent Sunday morning. He leaned back against the boat’s railing, allowing the sun to hit him full in the face.

Not long after the madman process of opening Surf Lodge in a mere seven weeks, Mr. Mulholland and his pals discovered wakeboarding: essentially, waterskiing on a snowboard. The Lodge’s hunky celebrity chef, Sam Talbot, whom they hired to make the fish tacos and jump-start the buzz, had fallen in love with the sport.

“My brew, you’re gonna love it,” Mr. Mulholland said. Other “brews” on board were his new COO, Frank Heidinger; Eric Han, a banker friend of his; and the guide/instructor Sammy Cooke, an Aussie who spends his summer in Long Island. (The question of what defining cultural differences exist between an Australian and South African dropped like an anchor between the two men, but Sammy confirmed for me that the saying the word “brew” is a telltale sign that the “mate” is from South Africa.)

Upon first arriving in Manhattan, Jamie made his way to the nearest pay phone and dialed a friendly barfly he’d met in St. Martin, a chef, who’d invited him to crash on his couch if he ever made it stateside. “He said, ‘Sure. Come over,’” Mr. Mulholland said. “I used to wake up in the morning in his little study; I used to sleep on the couch there, with him whacking away on the typewriter. He was working on a book at that time.” The chef was Anthony Bourdain. His all-night whacking would result in Kitchen Confidential, a national best seller. “I would walk from Tony’s place, which was at 115th and Riverside Drive, down to Houston and then come up the opposite side, looking for jobs at different bars,” Mr. Mulholland said. No dice. He didn’t have his papers.

Mr. Bourdain got him a few hours here and there de-shelling crab at the Supper Club. After three months, Mr. Mulholland moved on to the couch of another St. Martin pal’s house, in Jersey. He lived there for six months or so, doing odd jobs like building docks and selling silver jewelry at flea markets, till he’d saved enough cash to take another stab at Manhattan. 

He moved into the old Hotel 17, a hostel on East 17th Street. The rooms were tiny and it was a hive of transvestites. Mr. Mulholland, who grew up in a very conservative suburb of Cape Town and went to an all-boys boarding school, would triple-padlock the door of the shared bathroom on the rare occasions that he used it. “I remember seeing Amanda Lepore; she used to live right next door to me. I used to see her every morning,” he said. “It was very strange.”

WHAT WITH THE tiring job hunt, the weird but nice trannies and his fruitless ventures to open-call casting auditions, Mr. Mulholland said he almost lost his marbles. “I was literally down to nothing. I didn’t have money for the subway or anything. I remember Tony used to have a packet of grits in his cupboard and that’s all he had and I’d make myself grits and stuff because I didn’t have money for food.”

Then the French Roast manager gave him a break. Mr. Mulholland picked up every spare shift he could get. One time he worked 24 hours straight.

Robert De Niro used to come in. “You’d see him,” Mr. Mulholland said, “this established actor sitting in the restaurant, and then you’d go back and try to work just hard. That’s the thing that would drive you, like, ‘Well, he’s done it.’”

Jamie’s father, Gordon, had been a big-time soap star in South Africa. Over the phone from London, where he now lives with one of his other sons (there are three), Gordon, now 83, told me that Jamie never quite caught the acting bug. “He was a sweet, gentle boy,” he said. “He played rugby and cricket for the top schools.”

He remembered a time he took Jamie to the cinema:“We were seeing a newsreel from overseas, and there was a spot on Japanese parliament, and somebody said something in the parliament and they started attacking each other, literally, punching and that sort of thing—and he thought he’d be the commentator. A packed audience in the cinema, and here’s this little boy of about 6 or 7 started shouting, ‘Come on, South Africans, come on, South Africans!’ There wasn’t a South African involved, but from that day he learned how to entertain people.”

Back on the boat, Mr. Mulholland insisted all his guests go before him. “Mate, are you sure you’ve never done this before?” he asked me, as the boat circled back to get me after another awesome wipeout. “Brew, you’re a natural.” 

It was his business partner Mr. Heidinger’s first time braving the wakeboard as well. “You almost had it, brew,” Mr. Mulholland cheered. And then once his mate had had enough frustration for the day: “Those bindings are too small for you, brew.”

Mr. Heidinger met Mr. Mulholland in the early 2000s, when the latter was bartending at Lotus, a club in the meatpacking district. Two major developments had happened in Mr. Mulholland’s life in the interim between French Roast and Lotus. First and foremost, a Ford model named JoJo Loe sidled up to the bar.

“It was instant. We have spent every day together since then,” he said. They are now married, with a 2-year-old son named Ocean. “This woman grounded me and she gave me faith to follow what I wanted to do, as women do. It’s tough when you don’t have love in your life and you’re busting your ass; it’s a horrible place to be. She gave me support, a belief in my abilities.”

HE HAD LEFT French Roast and had started a catering company when childhood friend Brandon Kerzner, son of billionaire gambling tycoon Saul Kerzner, came to Manhattan. Brandon had a piece of Lotus and asked Jamie if he’d like a job as a bartender.

A couple years later, his skills with the movers and shakers caught the attention of the folks at PM Lounge, who hired him to manage the bar and their VIP list.

“I was sort of cultivating my client base and looking at spaces at the same time,” Mr. Mulholland said. “I just said to myself, ‘How much more experience do you need?’

In the mornings, he’d work on his business plan; each afternoon he’d carve out half an hour to go look at another space. He found a space on 27th Street. The only other thing on the entire block was Bungalow 8. “It was just perfect. I walked outside and I remember thinking, ‘Jesus, that’s a lot of money. Sixteen thousand a month.”

He had no credit history. But his old pal Kenny Goldie, a VIP from the old days with a very rich father, and Mr. Kerzner were in. Mr. Mulholland hired Jayma Cardoso, a voluptuous and business-savvy Brazilian cocktail waitress at Lotus, as operations manager.

Cain opened in October 2004, and the bottles haven’t stopped popping. “Less than a week after we opened, Mariah Carey had her Halloween party there,” Mr. Mulholland said. “And Puff Daddy rolled up in his Rolls and he stood on the roof in his Roman Emperor’s outfit, screaming at the crowd outside and came in with his entourage. Jayma and I were looking at each other, going, ‘Wow.’”

He said he is working on three more venues, two of which will be in New York and are expected to open by fall of next year. The third is in Dubai and will be a similar setup to Cain at the Cove, which is owned by Papa Kerzner and operated by Mr. Mulholland’s team. GoldBar, which opened on Broome Street in 2007, is an unmitigated success. Lenny Kravitz wrote a song about it on his new album. Surf Lodge’s business is up 15 percent since last year, Mr. Mulholland said, and has earned criticism for ruining quiet Montauk. But he said it’s a mellow scene.

“I remember looking outside, and at one table there was Steven Spielberg and [Jerry] Seinfeld. The table next to them was a local fisherman with his wife. It’s that diversity that makes Surf Lodge so special. It’s not about putting on these bullshit airs. It’s real, man. It’s just got this incredibly friendly and relaxed vibe to it. If anything, I think it embraces what Montauk is about.”

Recently, the baskets that dangle over Surf Lodge’s patio blew off in the wind. As soon as Mr. Mulholland put foot to ladder, the cops were there. A neighbor had called then to report signs of new construction.

“At that moment,” he said, “I thought that no matter what we do, there’s always going to be that one person who wants to bitch and complain. Maybe they’re not happy with their own life or whatever it is.”

Surf Lodge usually closes after Labor Day, but Mr. Mulholland is keeping it open until the end of the month to accommodate a couple of weddings and a Victoria’s Secret shoot. Which means another couple of sessions with Sammy the wakeboard hombre.

When it finally came time for the host to strap in, he zipped along admirably, did a few rail slides on the lip of the wake-way, then attempted a flip in midair and landed on his head. It was an epic wipeout. Ten minutes after that, he tried the same crazy idea. It worked.

“I’m still learning,” Mr. Mulholland said. “Every day.”

editorial@observer.com

“Fisher’s like a good-time guy,” said Gina Gershon, who’s been to more Fisher Stevens get-togethers than she cares to count. “He’s like the catalyst for a lot of stuff that happens.” 

Mr. Stevens, now 45, no longer eats meat after a pilot he did for a show called The Green Team, filmed on location at a slaughterhouse. He’s cutting back on fish too, after co-producing The Cove, a new documentary about the dolphin slaughter in Japan, and the reason for tonight’s celebration. He wasn’t drinking, either. He’d just returned from a week at Sting and Trudie Styler’s villa in Tuscany, where they host an annual, very intimate documentary film festival each year.

“It’s this incredible week,” Mr. Stevens explained to his friends, as they contemplated the wine and organic saki-based cocktail lists. “But every night was like, ‘Let’s go have a drink, let’s go drink wine!’ They make their own wine, and it’s insane!”

He’d made some new friends at Sting and Trudie’s, like Bobby Sager, a wealthy businessman–turned–full-time do-gooder upon whom the NBC show The Philanthropist is loosely based, as well as an amazing guy called Pablo who doesn’t speak any English and was involved in a doc about his fight with the oil companies responsible for a spill in the Amazon. Bobby and Pablo probably do not yet realize what that new friendship will entail—they’ve been entered into the human networking service that is Fisher Steven’s brain. 

“I’m so proud of Fish,” Ms. Gershon purred. 

I asked her if they had ever dated. 

“Our story is way too complex,” she said. “We met at Naked Angels, we didn’t like each other much at the beginning. And then one time we were having martinis and it just flipped and we were in love with each other.”

“Fisher and I were engaged for about a day,” offered playwright Nicole Burdette, also a founding member of Naked Angels, a downtown theater group that is still active. Ms. Burdette had come up with the name.

“I was the guy who got everyone together,” Mr. Stevens asserted. There remains some debate as to who exactly the original crew was, but aside from the ladies at the table, the other thespians Mr. Stevens brought together were Rob Morrow, Marisa Tomei, Ron Rifkin, Pippin, Tim and Sarah Jessica Parker, among others. 

The Cove is the first film that Mr. Stevens has been involved in since stepping down from his role at Greene Street, the production company he co-founded with producer John Penotti in 1996. There, too, his skills as connector were key. His good buddy Matt Dillon introduced him to the billionaire financier Louis Bacon, with whom Mr. Stevens started hanging, and who later invested $30 million in Greene Street. But life as a studio executive had lost its appeal for Mr. Stevens. More and more, money was getting in the way of his creative instincts. 

Just the other day, he told me, while filming a scene with Forrest Whitaker and Adrien Brody in Das Experiment, he thought to himself: “God, this would have been a great one for Greene Street, if only I had known then what I know now.” 

“The independent film business has changed,” he explained. “I mean we were the first company to take hedge fund money to make money, and then there was this big influx and now it’s like over again. And all those independent film companies are gone; you know, Warner Independent and Picture House, and you know all those small companies that used to buy our movies, and now they’re just giving them away. 

“You know Harvey’s kind of out of the game now, and once Harvey went out, it really hurt,” he said, of fallen mogul Harvey Weinstein. “’Cause he was really driving this whole industry.” But that’s no longer Mr. Stevens’s business. These days he’s all about documentaries, where there is no money to be made. Period.

“So I’m doing a new one in Africa,” Mr. Stevens said of his new project, which involves a polluted lake, or some such. “Dylan, did I tell you I’m going to Africa a lot now?” 

Sitting down at the far end of the table, Dylan Tichenor, who edits all of Wes Anderson’s movies, did not appear to be interested. “Tell us about that story I heard once, when you were in a white suit and you went wondering around Seventh Avenue. …”

Long story short: He was 20, in a white suit, accidentally took mescaline, ended up talking to a homeless guy, who convinced him that money didn’t matter in life, and then, after Fisher had passed out, robbed him blind.

Mr. Stevens got involved with The Cove through his friendship with another billionaire, tech guru Jim Clark. It was a connection Mr. Stevens came close to missing.

A girl he’d been dating named Jo said to come meet this guy who’s got a boat. 

“I thought, ‘I don’t need to meet this rich guy and a boat,’” he recalled. “And she says, ‘Do me a favor and get this book called The New New Thing and tell me you don’t want to come.’ So I get the book by Michael Lewis and I say, ‘I’m coming.’ The book is about Jim and I think, ‘This guy is a maverick.’ The other truth is, I had a friend of mine was going as well, so we went together. The boat was in Antigua. So Jim goes, he’s leaving and I said, ‘You can’t go man,’ and he asks if I drink and I say yeah, and I don’t know much about wine but he opens this Volnay ’61, which we drank in like five minutes. And he goes, ‘Nobody here drinks, I was going crazy,’ and then he didn’t go and we ended up having the best week, and that’s how we connected, and we stayed friends.”

Funnily enough, the next time he saw Mr. Clark was in Papua on his boat, but it was a new boat. Turns out he’d sold the Hyperion to some British guy named Louis Bacon.

“I was like, ‘Louis is American! He’s my old partner,’” he said. On that trip, Mr. Stevens had brought along a copy of Crazy Love, another doc that he co-directed. Mr. Clark was impressed and not long after asked Mr. Stevens to help him with The Cove. 

“He has a lot of interesting friends,” said Griffin Dunne over the phone. He was out in L.A. working on a script and staying in Mr. Stevens’s apartment. “You’ll probably hear from everyone that no one tends to pack as much life in as Fish; he’s been grabbing it with both hands lately.”

Mr. Dunne gave Mr. Stevens his first acting job, a bit part in Baby it’s You. Mr. Stevens, he says, has returned the favor in spades. 

“He is certainly a well-connected and well-loved person by a lot of people, many of which don’t know each other—and if they do know each other it’s only through Fisher—who are all doing interesting things in their lives,” he said, adding that Mr. Stevens, Liev Schrieber and a set designer named Happy Massee have an ongoing tennis scene. “I think that is the best image I have of Fisher, his general enthusiasm that he has about life, the way he embraces life. He had a particularly nasty skin cancerous mole removed from his neck a couple of years ago, and they patched him up with tape, and it was pretty gruesome-looking, and it was one of those ‘keep it dry’ and ‘don’t move too much’ bandages, but it was a really hot day and he saw a pool and just went, ‘Oh my God, look at that pool, I gotta go in!’ And he just runs from about 20 yards away and dives into the pool with the bandages. And he hits the water and goes, ‘Ow! Ow! The water is so great, ow!’ It was like he had a choice, either go with the doctor’s orders or dive into the blue water; he’ll go for the blue water.”

Mr. Dunne said that it is Mr. Stevens’s joie de vivre that accounts for his remarkable success with women. Mr. Stevens, who’s probably best known for playing a quirky scientist in Short Circuit, dated Michelle Pfieffer.

“What will start off as just a one-on-one dinner on their first date will move on to these fantastic experiences,” Mr. Dunne explained. Like what? Skinny-dipping in the East River? 

“Well … yeah … usually they end up nude, in one environment or another!” Mr. Dunne said with a laugh. He said the diversity of the women Mr. Stevens has dated is also a reflection of his curious nature: doctors, editors, actresses, different races, heights, ethnicities. 

A few years back the Naked Angels held a fund-raiser. Mr. Stevens volunteered to be the subject of a roast. 

Mr. Dunne again: “Everyone got up and roasted the shit out of Fish. A lot to do with women and fucking … and it sort of transcends his physical appearance, which is not what one would associate a guy who looks like Fish being with such beautiful women, and how the fuck does he do it?? It was a noble expression of his to put himself in that position to raise money for this group. It was also pretty taxing on his identity, I think.”

“He’s been spending an awful lot of time at yoga studios—which I would normally say, ‘He’s trolling for victims’—but I guess not. I think he recently got into a serious relationship,” said another friend, Matt Dillon, on the phone. 

Mr. Stevens, currently dating a model and yoga instructor, said he’s looking to settle down. “There comes a time when you gotta grow up,” he said, when I pressed him on the issue at dinner. 

But that doesn’t mean no more dinner parties. 

“I go out a lot,” he explained. “My mother worked at night. Since I’m 13, I been eating out. I had an account at a Chinese restaurant—Jen’s Kitchen—across the street, when we lived on 13th street.”

He said that during the time he’s lived with women, he has eaten at home in Dumbo.

So you’ve lived with women before? 

“Yes,” he said. “And I’d like to again.”

“I like to cook, Fish,” Ms. Gershon said.

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