Illo: Oliver Munday.

“Happy 9/11, everybody!”

It was actually September 9, nearly ten years after the attacks, and comedian Nick DiPaolo was on stage at the Gotham Comedy Club, where he’d been headlining, taking a chance that with a decade’s distance audiences might finally be ready to laugh—not about the thousands of dead, of course, but maybe about our shared anxieties and the collective experience of living with tragedy and fear.

Instantly, the house went cold, almost dead. Mr. DiPaolo, a 25-year standup veteran looked thrown for a moment. He paused, cocking his head and shooting the audience a look of disapproval, then he pushed on with his rant. “I want to call 311 and say, ‘I fucking saw something and so I’m saying something! I saw two fucking planes crash ten years ago! Do you remember that?’”

The audience erupted into an almost primal frenzy of cheers. For the remainder of the evening’s show, though, he’d steer clear of the topic. They say comedy equals tragedy plus time, but how much time exactly? When is it “too soon,” and when is it perhaps too late?

“Being offended has everything to do with what it is that the listeners cherish and value at a particular time,” Paul Lewis, a professor of English at Boston College and the author of Cracking Up: American Humor in a Time of Conflict, told The Observer. “At different times in your life you have a stronger or weaker commitment to a given idea or image and you do or don't want it messed around with in a joke. A tactful comedian knows that for any particular audience there are lines that should not be crossed.” For instance, he said, a dead-baby joke might land very differently for a group of teenagers than it would for the same audience ten years later, when they’re having children of their own. “A line has appeared, right?”

New York’s first responders and the construction crews on the Pile took incalculable risks in the hours and weeks after 9/11, but comics took some risks of their own, and while the results might not always have gone over well, they were generally part of an effort to help people process the experience, and the uncomfortable emotions it gave rise to. Gallows humor is a survival technique, after all. When a comedian makes a successful joke in response to a real tragedy, it can awaken an audience’s defiant spirit; when the joke bombs, it just pisses them off.

Contrary to Mel Brooks's famous line from The 2000 Year Old Man—"Tragedy is when I cut my finger. Comedy is when you fall into an open sewer and die”—according to a number of comics, the 9/11 jokes that really, well, killed in the early days tended to be those that targeted either the terrorists themselves or the comedians’ own failings and anxieties. Much was made of the response by The Onion—newly transplanted to New York from Wisconsin—which included such headlines as “American Life Turns into Bad Jerry Bruckheimer Movie” and “Not Knowing What Else to Do, Woman Bakes American-Flag Cake.” David Letterman returned to the air six days after the attacks, with a heartfelt monologue that was perhaps most notable for its earnestness and lack of humor; his only jokes were about his hair, Paul’s lack of hair, and guest Regis Philbin: “Thank god Regis is here, so we have something to make fun of.”

In the city’s comedy clubs, stand-ups were free to take more chances. Comic Jim Norton recalled that after beginning gingerly, his bits became more aggressive. “As time went on, I began expanding, shitting on the hijackers, talking more in-depth about it,” he said. “I never once said anything against the people who were murdered. One woman in Long Island began heckling me and I started slamming her. I was getting more and more aggressive when someone at her table looked at me, kind of pleading, and made the ‘please don’t’ face.” Realizing the woman may have lost a relative in the attacks, he backed off.

Mr. DiPaolo recalled that he first tried addressing the attacks just two nights after 9/11 at the Comedy Cellar in Greenwich Village. “I went downstairs, and there were only eight or nine in the audience and I went on a rant about terrorists and they loved it! How could you not talk about it?” His jokes targeted Muslims—cathartic, perhaps, but maybe you had to be there? “The FBI has trouble penetrating these terrorist cells,” he said. “Bullshit. Move to my neighborhood, I've been buying fruit from the Taliban for four years.” Asked to recall a joke that bombed, he offered, “Every Mosque in this country should be on fire.”

Marc Maron recalled taking a similar approach. “I had a joke about Osama working at the deli down the street from me in Queens,” he told The Observer. “I got into a little trouble because my instinct wasn't immediately, ‘These are the guilty parties...let's start profiling.’ It became very heated.”

“There are no rules in comedy—period,” Mr. DiPaolo said. “If I died tonight, I hope my friends would be making jokes at my funeral tomorrow. That’s the beauty of comedy.”

According to Mr. Norton, no subject is completely taboo if it’s approached with the right intentions. “Americans have gotten so obsessively hypersensitive and they expect comedians to be the same way,” he said. “Every event, no matter how terrible, is fair game in comedy. None of us wanted to start making fun of people jumping from the buildings, the victims, shit like that. We made fun of our own reactions to the tragedy.”

Roseanne Barr has never been one to shy away from controversy, once posing in a photo spread for the alternative Jewish culture magazine Heeb wearing a Hitler moustache and a swastika and preparing to take a bite of what the caption referred to as “burnt Jew cookies.”

“Laughter is the greatest weapon there is,” she told The Observer. “To laugh things to scorn ends their effect.” However, the actress, who noted that she has plans to run for President in 2012—as the candidate for the “Green Tea Party”—added that she still draws the line at 9/11 jokes. “I think its too huge,” she said.

Comic Gilbert Gottfried made one of the more controversial 9/11 jokes two weeks after the attacks, during Comedy Central’s Roast of Hugh Hefner. The now infamous crack, which was cut from the show but appeared in the critically acclaimed documentary about taboo humor, The Aristocrats, was this: “‘I have a flight to California. But I can’t get a direct flight—they said they have to stop at the Empire State Building.’”

“There was still smoke in the air, and I wanted to be the first one to tell a poor taste joke and shock people out of their stupor,” Mr. Gottfried recalled.

Though the joke eventually gained Mr. Gottfried respectability, he said, the initial reaction was negative. “First there was a gasp and a lot of angry grumbling,” he recalled. “Some people booed, moaned and hissed, and one guy yelled out, ‘Too soon!’ I thought that he meant that I hadn’t taken enough time between the set up and the punch line! Someone tweeted at me the other day and wrote: ‘You make me laugh when I don’t want to,’ and that’s what I’ve felt for years I have felt I’ve done.”

Mr. Gottfried, who recently lost a gig as the Aflac duck after unleashing a series of questionable tweets about the Japanese tsunami, said that he wouldn’t repeat the 9/11 joke for an audience, but not for the reasons one might expect. “Now it’s past the shock point, and I like it when it’s shocking,” he said. “I always wanted to know where the person is in a big office who measures the amount of time and says, ‘Now you can say this!’” he added. “I feel like a person who wears a little ribbon on their lapel, or whatever is the latest thing, is no more sensitive or caring than somebody who cracks jokes about it.”

Joan Rivers delivered a 9/11 joke the same evening (it was also cut from the broadcast). The terrorists are going to win, she said, "...they’re gonna win because they’re ugly and horrible and they can slam into a building and they get 72 virgins. What’s a Jewish guy going to get? A 50-year-old woman who still won’t swallow."

Sarah Silverman deployed her signature brand of faux-naiveté, suggesting, “If American Airlines were smart, their slogan would be: ‘American Airlines first through the towers,’ because it is something in which they came first.” Louis C.K. opted to use the event to mock himself, theorizing, “You can figure out how bad a person you are by how soon after September 11th you masturbated. And for me it was between the two buildings going down. And you know, I had to do it. Otherwise they win.”

That night at the Comedy Cellar, with the fallen Trade Center still smouldering, Mr. Norton recalled, “A bunch of comics were hanging—myself, Patrice O'neal, Keith Robinson, Greg Giraldo, Chris Rock—and we started to talk to each other about thoughts we’d had about what we would have done if we were on one of the hijacked planes. We realized, like asses, that we all had these embarrassing fantasies of saving the day in that situation. So we went onstage and began talking about our individual fantasies, and the crowd loved it. They all related to it.”

Mr. Giraldo, who passed away this year, remembered the night fondly, turning it into a bit: “There wasn’t even electricity in some parts of the city, but we started doing shows because people seemed to want to come out; they seemed to want to laugh,” he would tell audiences, adding, “There were bachelorette parties, and I thought, Holy shit, I never thought that I would be proud to see a pack of drunken Jersey girls with condoms on their heads.

“I thought, Shit they are never going to be able to change the American way of life.”

Settling on a home for Ms. Silverman’s book has been a long and drawn-out process that began in mid-November, when an intense auction overseen by Trident Media Group CEO Dan Strone ended with HarperCollins prevailing over several other houses with a stunning $2.5 million bid submitted jointly on behalf of Mr. Hirshey at the Harper imprint, Gillian Blake at Collins and Laurie Chittenden at William Morrow.

To be sure, winning the auction for Ms. Silverman’s book was a victory for HarperCollins, but the fact that all three of its major nonfiction imprints wanted to publish it meant that Mr. Hirshey, Ms. Blake and Ms. Chittenden would have to compete for it with each other in an unpleasant in-house ritual known as a “beauty contest.”

Such situations—in which an author must decide which editor is best suited for his or her project based at best on a brief meeting and a few emails—come up regularly in publishing these days. This is partly because all four of the really big New York houses own a number of imprints with similar or indistinguishable publishing programs, and partly because reliably lucrative, celebrity-driven titles like Ms. Silverman’s move increasingly timid editors to compete with each other more ferociously than ever before.

At best, these beauty contests are awkward. At worst, they can breed resentment among friends, and stoke intramural rivalries between different units of the same company.

That’s not to say that that’s definitely what happened with the Sarah Silverman book, though it probably didn’t help that she and her agent kept the HarperCollins people waiting so long while she made up her mind.

Originally, Ms. Silverman was supposed to talk to them all last Friday, but something involving her television show on Comedy Central forced her to cancel and reschedule for this past Tuesday. Even then, rather than coming in for a proper meet-and-greet, the best Ms. Silverman could offer was a series of video conference calls that had the editors from HarperCollins talking to a life-size projection of Ms. Silverman’s face beamed in from Los Angeles onto a screen at the Fifth Avenue New York headquarters of the Creative Artists Agency.

Several sources described it as really weird. They got there sometime in the late afternoon, and spent the first few minutes sitting around in a waiting lounge that was so stiflingly hot that Mr. Hirshey had to take leave of the group and get a beer. Top HarperCollins executive Michael Morrison, meanwhile, who makes it his business to mediate these beauty contests whenever they arise, was in the meeting room chatting with Ms. Silverman and making sure all was in order.

Each of the three editors came armed with a different strategy. Ms. Chittenden of William Morrow, apparently a believer in the idea of power in numbers, brought along not just her publisher Lisa Gallagher, but also deputy publisher Lynn Grady and director of publicity Seale Ballanger. Ms. Blake, meanwhile, from the Collins group, went slightly less heavy and brought along just her boss, Steve Ross. Mr. Hirshey, for his part, came alone—a risk, he said yesterday, that he was emboldened to take because he felt he was "a tough enough Jew” to handle Ms. Silverman by himself.

"I spent most of my time reciting my bar mitzvah speech," a happy Mr. Hirshey said, referring to the fact that, culturally speaking, he had something of a home-court advantage over the other editors in the race for the Jewish comedienne's heart.

A recommendation from magazine writer and biographer Bill Zehme, a friend of Ms. Silverman’s whom Mr. Hirshey edited for seven years when he worked at Esquire, probably didn’t hurt, either. "I told her Hirshey’s a hero," said Mr. Zehme. "Nothing specific—just that he's aces. They’ll be swell together."

Mr. Hirshey said he’d prefer to believe the outcome of his face-off with Ms. Blake and Ms. Chittenden had more to do with the best sellers he has edited by comedians like Rodney Dangerfield and Dennis Miller, as well as the fact that he and Ms. Silverman see eye to eye on what the book she's writing should be.

"I think we both see the book as Sarah bringing her overarching sunniness to life’s darker moments," Mr. Hirshey explained. "No comedienne out there is funnier about depression, death, religion or bed-wetting. It’s that juxtaposition of light and dark that will be at the heart of the book. Or, as I like to think of it: equal parts gravitas and gravlax."

Mr. Hirshey said that while a publication date for Silverman’s book has not yet been set, he hopes to see it out sometime next year.

At this point, Mr. Seinfeld's deal looks like it still hasn't closed, but the sheer number of commas Mr. Strone is juggling has stunned many in the publishing industry.

Media Mob spoke to the seven figure agent—who has brokered deals for Stephen Colbert, Jon Stewart, and Paris Hilton—by phone this morning and put before him the concerns of the book industry's most anxious critics.

Below, our Q&A, with some of the questions recreated post-facto from memory and some of Mr. Strone's answers edited for clarity.

What's happening with the Seinfeld book?
I have nothing I can say on that. I’m not making any comment.

Is it becoming more common for book projects to go out to publishers without proposals attached, the way these two did?
I do both. I have books that I sell with detailed proposals. It just depends on the situation and the particular person involved. I’ve been doing this a long time. I have pretty good instincts about what the market is.

What are some other celebrity-driven deals of this scale that you’ve done recently?
There’s been so many—I’m trying to think. There was the deal for Anthony Zuiker, the creator of CSI. There’s the Buzz Aldrin book that is coming out July 20th. Belinda Carlisle, Melissa Gilbert. I just sold Tori Spelling's second book. I did Roger Moore's book, My Word Is My Bond.

Do you think the economic environment makes these celebrity-driven books more likely to attract interest from publishers than they used to?
I think there’s always going to be a market for books that publishers think are going to sell a lot of copies. People don’t spend money on stuff unless they think they’re gonna make money. That’s just common sense. You’re not gonna report something you don’t think anyone cares about, right? It’s the same thing. People are bidding, competitively, in a marketplace. What can I say? I mean, I don’t make people spend the money.

Do you think those big books are compelling publishers to pull back resources from "midlist" books, the ones that don’t go for a lot of money because the author isn’t well-known or the book isn’t obviously commercial?
I think there is a sense of belt-tightening in that area. I feel that is evident at this time. You should ask the publishers. I’m one step removed.

What do you say to the people who were horrified last week to hear about these multimillion dollar deals of yours?
I don’t know why they should be horrified. As I say, nobody is forced to spend the money. People don’t spend the money unless they feel it’s a good investment.

There is a concern that publishers feel cowed, and out of timidy are only willing to pick up books that have built-in audiences.
What’s wrong with that? What’s wrong with knowing you have a built-in audience? [How is it any different] if you’re talking about a name-brand fiction author? Do you think it’s wrong for a publisher to spend a lot of money on Dan Brown or John Grisham or James Patterson? It’s the same thing. It’s a built-in audience, it’s just that they’re a slightly different business model.

Did you have reservations about going out with two such huge books in one week? Is there an argument to be made for spacing them out?
I suppose you could make an argument for spacing them out. But, no, I didn’t have a problem with it.

HarperCollins' number two Michael Morrison, who will oversee the so-called beauty contest between the three imprints, said he was talking to Mr. Strone about the possibility of having Ms. Silverman come in and meet with editors and publishers from all three imprints before making her choice. Though Mr. Morrison said there is no rush to come to a decision, one would not be wrong to suspect that the folks at Harper and Collins—imprints that tend to acquire very similar kinds of books when it comes to nonfiction and thus find themselves in competition with relative frequency—are eager for an outcome to come sooner rather than later.

Ms. Silverman's book, by the way, will be a collection of comedic essays, just like the Tina Fey book that Endeavor agent Richard Abate recently sold to Little, Brown for a reported $6 million. Apparently that's actually how Mr. Strone described the Silverman project to publishers: "Just like Tina Fey."

One of Mr. Strone's other clients, meanwhile, ex-Microsoft sponsor Jerry Seinfeld, has a book on the market this week that is said to have driven at least two publishers crazy enough to submit bids in the $7 million to $8 million dollar range. Unclear whether that auction is over, or when Mr. Seinfeld will settle on a publisher, but judging by the reaction Media Mob has heard from agents, literary scouts and publishers who aren't pursuing the book, whoever ends up winning is going to have some explaining to do. As one scout put it in an e-mail, "For serious, who has that kind of money? Isn't the economy collapsing or something? How does giving Jerry Seinfeld more money seem smart to anyone?"

The art world remembered Robert Rauschenberg at a Coalition for the Homeless benefit. 

We spent an anxious Election Eve with Graydon Carter, Tina Brown, Salman Rushdie, Regis Philbin, and Nora Ephron at the New York Public Library’s Library Lions benefit. 

On November 4th, we saw many people and did many things. Some highlights: chatting with Project Runway's Austin Scarlett at his polling place, drinking with bloggers in Cobble Hill, spying on Susan Sarandon backstage at Comedy Central, avoiding death by Kool-Aid with Overlook Press, discussing potential First Lady fashions with Angel Sanchez, and comforting Republican Georgette Mosbacher at the Harvey Weinstein/GQ party. 

Tina Brown, Harry Evans, Ian McEwan, and Joan Didion thought about the future while toasting the Dominick Dunne documentary After the Party.

After polling Sarah Silverman, Martha Stewart, and Anne Slowey, we concluded no one above high school age wears Juicy sweatpants (with the exception of Vogue darling Julia Macklowe).

The organizers of Thursday evening's opening party for the label's new, 12,000 square foot flagship store at Fifth Avenue and 52nd Street had taken Ms. Wilson's words to heart. Outside the store, a small army of male models dressed in tight black Levi's, tuxedo shirts, ripped blazers, marching boots, bowler hats, and pink flowers in place of bow ties stared at guests through their emo eye-liner with monotone facial expressions. Inside, professional ballerinas in tutus twisted into ballet moves along the steps leading upstairs. Violinists scratched away at their instruments. Colorful little cakes were passed out. A gospel choir performed. And the publicist Leslie Sloane Zelnick was nearly responsible for a few broken limbs when she entered with her client Penn Badgley, accompanied by his Gossip Girl co-star and real-life girlfriend Blake Lively, Sex and the City hunk Jason Lewis, Sarah Michelle Gellar, and Gretchen Mol, sending gaggles of lip-glossed tween girls in a stampede towards the door.

In addition to the Hollywood celebrities swarming the spaces, there were plenty of unexpected guests. The Daily Transom found Martha Stewart snapping photos of the decor with a digital camera. Could it be that Ms. Stewart is a fan of the aforementioned sweatpants?

"Ah, yes, the ones with Juicy written across the derriere," Ms. Stewart said. "I doubt I can ever wear those. I cannot even imagine that one thing would fit me in here--it's so tiny-tiny!" (Ms. Stewart pointed out, however, that the little frosted cakes were delicious.)   

"This actually seems like a very Gossip Girl kind of venue here," said author and recent Gossip Girl guest star Jay McInerney, who we found hanging out by the bar with his wife, socialite Anne Hearst. Mr. McInerney told the Daily Transom that while he and Ms. Hearst do not wear Juicy, his 13-year-old daughter is a fan. 

"She loves this stuff. She's been a Juicy girl for a while now," said Mr. McInerney. But the Juicy butt pants are off limits for Maisie McInerney.

"No! I don't let her do that," Mr. McInerney said. "She is only 13!"

As for his Gossip Girl cameo, the author would like to make a comeback. "I'm just waiting for the call," he said. "I love the show and I actually got to do a little bit of acting for once. Normally, I go onto a show and I'm Jay McInerney, I say hi and I walk off."

Stylista judge and Elle fashion editor Anne Slowey, whose patent leather six-inch platforms drew whispers from the humbly dressed editorial assistants in the room, was amused by the kitschy decor. 

"I was just saying that the store is twisted and perverse in that Argento '70s slasher film sort of way," she said. "I keep waiting for one of these ballerinas to freak out with a shard of glass." 

We wondered whether Ms. Slowey picks up her carefully prepared lattes on Saturdays in a pair of Juicy sweats.  

"No, no. I don't have anything with letters in my closet," said Ms. Slowey. "I'm actually on strike right now at the office until they turn the heat down. I keep a rack of clothes in my office and I'm wearing the same leggings and tank top every day. We're going on about two and half weeks and I'm refusing to change or wash my clothes."

We couldn't figure out if the typically well-kept Ms. Slowey was joking. 

"No, really! No one has taken me seriously and it's so hot in the office that I'm in, like, pajamas. It would actually be a step up for me if I got a pair of clean, fresh Juicy sweats," the fashion editor continued. "I haven't gone so far as to bring lingerie, a nightie and bathrobe into the office, but maybe that should be my next move. I've made everyone aware that I won't dress until they turn down the heat!"

Actress Jennifer Jason Leigh, accompanied by her husband, filmmaker Noah Baumbach, also conceded that she's not "bold" enough to pull off the candy pink Juicy sweatpants. Funny lady Sarah Silverman, who was thumbing through the racks of colorful clothes, agreed.  

"I can't! My ass is just not Juicy, it's very flat. Like the ass of a young boy," Ms. Silverman told the Daily Transom. "I can wear it ironically, but I wouldn't be the first one to make it a joke because it's behind me and I'd have to turn around constantly and be like, 'I know! It's ironic!'"

So just who are the slouchy Juicy butt pants for, then? 

"It's for people with juicy asses!" she replied.

Like the crowds of 14-year-olds running around the store?

"No! Nobody should be looking at a 14-year-old's ass and reading Juicy!" she said. "I mean if they get molested... I'm just saying."

The Daily Transom had all but given up on finding a party guest who was a proud Juicy butt-pant wearer. But then we ran into the stylish portfolio manager for Sigma Capital Management and recent Vogue It Girl Julie Macklowe. Ms. Macklowe was dressed in head-to-toe Chanel (including over-the-knee white leather boots) and surely doesn't wear a pair of sweatpants with the word Juicy written across her backside.  

"I do actually. But please don't tell!" she replied. 

Michelle Rodriguez woke up her fellow guests at Florida's Mayfair Hotel by banging the door knocker to her room and screaming at her female "roommate." [R&M] 

Female employees of Hawaiian Tropic Zone are suing parent company Riese for $600 million over charges of physical and sexual harassment and rape. [NYP via Grub Street]

Christie Brinkley's ex-husband, Peter Cook, is finally sharing his side of the story in an upcoming interview with Barbara Walters. His explanation for having an affair with his then 18-year-old assistant?  "I was seeking a connection I could not find in my own marriage...I wanted a little acknowledgment, a little attention, a little thank you every now and then for my efforts, for the amount of time I took to care for her and my family, for the wealth I was building." [NYDN] 

Comedians Jimmy Kimmel and Sarah Silverman seem to be back together, but they're "not defining" the relationship. [US Weekly]

Nick Nolte is recovering after being injured in a fire that destroyed his California home. [Star]

Christian Slater got a GED to set a good example for his kids. [P6] 

Jimmy Kimmel and Sarah Silverman's reps confirm their break-up. [Vanity Fair]

Friend to Christie Brinkley and Today show contributor, Jill Rappaport is reportedly handling all press for the recently settled divorcée, granting the first televised interview to the Today show. Ms. Rappaport is also apparently telling other outlets, that if they want any information, they have to introduce her as "Today show correspondent and renowned entertainment journalist." [P6]

Sienna Miller confirmed her relationship with oil heir and actor Balthazar Getty, who happens to be married and have four children, by making out with him in the nude in Italy. [NY Daily News]

Project Runway winner, Christian Siriano, is working on a hair product with Tresemme called Fierce Hair. [Details]

She also weighed in on the Democratic primary (“I like the black guy, but I like Hillary, too”) and joked about approaching Barack Obama nervously at a Los Angeles fund-raiser and asking, “‘Senator Obama, what are you going to do to reduce the national debt?’”

“And he said a really interesting thing. He said, ‘I’m Kanye West.’”

CBS anchor Katie Couric arrived late and very tired from Chicago, where she’d spent the day shooting a feature for 60 Minutes, and descended the stairs to an after-party with the actor Rob Morrow, who had emceed the event. “I think she’s really funny,” she said of Ms. Silverman. “Really crude. But really funny.”

What was her favorite joke of the evening? “Some of them were pretty outrageous,” said Ms. Couric, who was clad in a shiny, sleeveless gown. “I don’t want to say they were that funny because then who knows what kind of brouhaha it would create?”

Mr. Morrow had introduced Ms. Silverman by declaring that it was him, and not the star Matt Damon, with whom she had been infamously intimately involved, as explicated in a hit video short. “There’s not a lot of people she trusts with her stool,” he explained, in case the audience missed it the first time.

At the party, Mr. Morrow was approached by a wide-eyed woman with blond curls. “Are you really her lover?” she asked, with apparent sincerity.

“No,” Mr. Morrow replied. “I wish.”