“Everything’s just become too vanilla,” he continued. The unspoken assumption, of course, was that Mr. Kirshenbaum was one of the last true badasses in a business that has become neutered in the last 10 years.

Mr. Kirshenbaum, whom Us Weekly recently named one of New York’s 25 most stylish people, was wearing a navy blue suit with lavender pinstripes—bespoke, as most of his suits are—and a matching lavender pocket square and rather tight white shirt. His mane of blond hair was highlighted; he had stubble on his cheeks and just a hint of a goatee; a pair of glasses hung casually at his chest. The effect was 21st-century Austin Powers meets David Beckham. (Mr. Kirshenbaum reportedly once referred to himself as “the greatest metrosexual of all time, aside from David Beckham.”)

He spoke about an intern of his who came to work wearing a paper bag on his head, with holes poked out for eyes. This, he told the crowd approvingly, was an example of how advertising agencies need to allow creative people to just do their thing.

Later, Mr. Kirshenbaum elaborated via telephone. “The business has gotten a bit more bland,” he sighed. “There aren’t as many personalities as when I went into the business. There were different types of agencies, and each one was representative of the founder.”

But so what? Is it so terrible that the age when, as the AMC series Mad Men—which, in its first season, has followed the fortunes of a fictional ad agency called Sterling Cooper in 1960—shows us, admen were larger-than-life figures, is over? That a copywriter is now likely to get a blank stare when he proudly relays the tag line that he came up with to sell dishwasher detergent or convertibles or cold medicine? Eager college graduates used to move to New York to seek their fame and fortune in the glass and steel skyscrapers on Madison Avenue; advertising was seen as a sexy industry that offered the perfect combination of business and creative skills, and attracted thousands of failed novelists, hobbyist painters, moonlighting poets. They were attracted by men like David Ogilvy, who once said in his trademark Scottish brogue, “If you can’t advertise yourself, what hope have you of being able to advertise anything else?” He was wearing a kilt and a cravat at the time; when he retired, he moved to a 60-room castle in the south of France.

The era portrayed by Mad Men (which AMC just renewed for a second season) is an alluring one: three-martini (sometimes four- or five-) lunches, smoking in the offices, lots of extramarital affairs. (Of course, it was an alluring world largely for men; women were almost entirely confined to the typing pool and the beds of their bosses.)

“The glory days of advertising just aren’t around anymore,” sighed a 28-year-old copywriter at a large agency. “The multimillion dollar account and cocaine in the boardrooms are fewer and farther between. And now, you can’t ethically have an expense account and take clients on crazy vacation shoots.” Tant pis, mon chou! “It’s not to say it’s without its perks or glamour, but the persona of the power suit is playing for much lower stakes now, and the unchecked excess of that whole industry is such that it’s much more regulated than it used to be.”

That also might be because there’s simply less money floating around advertising today. The ad sharpies in Mad Men think nothing of taking clients to 21 and Toots Shor’s, skipping out for an afternoon romp with their mistresses, or—in one difference that undoubtedly resonated—buying a co-op at 83rd and Park as a junior account executive. (“It’s $32,000, but the agent thinks we can get it for $30,” the man’s wife tells him excitedly.) All the money was largely due to the industry’s fee structure, which paid agencies a 15 percent commission on whatever its clients’ media spending was.

“If a client spent $100 million on media costs, the agency used to get $15 million,” said Nina DiSesa, chairman of McCann Erickson’s New York office. “A lot of money was going around in those days! Today, the cost of doing business may be the same, but we don’t entertain the same. The relationship with the client is not based on entertainment; we don’t go out drinking. People don’t have time for that now, because when a campaign fails, you get fired.”

“When I first started, it was pretty decadent—people working drunk and everything—but it’s definitely lessened over the years. The whole decadence thing in advertising is kind of looked down upon,” said Mark Duffy, a copywriter who’s been in the business for nearly 20 years and writes the Copyranter blog.

At the same time, the types of clients who want a large agency to handle their advertising have changed. On Mad Men, Sterling Cooper competes for business from Bethlehem Steel and Richard Nixon; today, some of the biggest money in advertising comes from pharmaceuticals, which don’t offer the same cachet. Try telling the girl you just met at Soho House that you work on the Cialis campaign.

“It’s hard to be a ‘mad man’ in 2007,” said Ernest Lupinacci, who runs a brand consultancy and was a founder of Anomaly, a small agency that’s quickly become one of the leading independent firms in New York. That may also be because there are simply fewer of them; since 2000, according to Advertising Age, ad agencies have lost 18,600 U.S. jobs, or around 9 percent of their workforce. At the same time, the number of marketing consultants such as Mr. Lupinacci have jumped by nearly 58 percent.

In October 1962, Time magazine put the 12 leading advertising men in the country on its cover. These were men like J. Walter Thompson’s Norman Hulbert Strouse, whom the magazine described as “wearing a toothbrush mustache and half-rimmed glasses … In his spare time, Strouse turns out handsomely designed pamphlets on a hand printing press in his elegant triplex on Manhattan’s Beekman Place.” Just as Mr. Ogilvy’s big idea about the Big Idea being central to successful advertising is now antiquated, so too have the space for big personalities in advertising faded.

The implication used to be, if an agency’s chairman was bigger than life, he could inflate your product to similar proportions. A former employee of Mr. Kirshenbaum’s tells this story: “Richard once went to the Bahamas on vacation, and couldn’t get WiFi in his hotel room. They had high-speed wired Internet, but he didn’t want that. So he called the front desk and said, ‘How much to make this entire hotel wireless in under an hour?’ They said, ‘$10,000.’ He said, ‘It better be under an hour.’ And it was done.” When queried about the veracity of this tale, Mr. Kirshenbaum said, “It’s not not true.”

Today, as Mr. Kirshenbaum pointed out at the panel, firms are less likely to bear the founders’ names on the door, and more likely to have a name like StrawberryFrog (or Mother or Anomaly). A big personality can leave the industry and find that his blog has landed him a book deal or television show. Why waste personality on an industry that doesn’t seem to want it anymore?

Would anyone care if 12 advertising executives were placed on the cover of Time today? And it’s almost impossible to imagine an adman (or -woman) being made a Commander of the British Empire or elected to France’s “Order of Arts and Letters,” two honors that were bestowed on Mr. Ogilvy.

“The kinds of personalities and individuals who used to migrate to the advertising industry because of the appeal of working in that industry still exist, but you’re more likely to find them applying for jobs at Google,” said Mr. Lupinacci. “The sensibility of what it means to go work at an ad agency, because of how interesting and irreverent and provocative the industry was—it’s just not there anymore.”

That’s not to say that ambition is dead. The image of advertising in the popular imagination is, it turns out, a hard one to shake and to this day is not entirely untrue. “I thought the industry was so glamorous,” says a 25-year-old former account executive at a midsize agency. “I went to FIT, and my teachers in the advertising and marketing programs were all high-profile. They spun great tales of mingling with celebs at all the parties you see on TV and read about in the papers. And our agency was like high school: all the young kids fucking in the closets. I once got ass on our conference table at 2 a.m. after I stuffed press kits by myself all night. There was also a lot of coke—I once saw an intern cutting lines in the bathroom!”

Indeed, in an industry that, like other media industries, pays a starting salary that’s somewhere in the range of $30,000 a year, a certain level of perquisites is expected. “I used to go on ski trips and surfing camp, and any concert I wanted to go to,” said a former associate media director at a number of large agencies. “Publishers would rent out summer houses for you, and I went to the best restaurants in New York all the time.”

But: “It’s one thing to sip champagne next to whomever at a gala,” said the 25-year-old former account exec. “It’s another thing when you can’t pay your rent.”

In any case, advertising has been usurped by public relations as the industry of choice for those seeking a route to glamour. It’s ironic, of course, because P.R. used to be the industry whose leading practitioners were invisible; a good P.R. agent never let himself usurp his client’s fame. Today, Heidi Montag, one of the stars of MTV’s reality show The Hills, looks pretty behind the desk of an L.A. publicity agency whose founder, Brent Bolthouse, is perfectly content to let the camera linger on his carefully slicked black hair. And thus, a whole generation of teenagers is indoctrinated in the joys of clipboard-holding.

They had David Ogilvy; we have Heidi Montag.

It's so great to get a celebrity endorsement on the back of your book! When Richard Kirshenbaum and Daniel Rosenberg's Closing the Deal: Two Married Guys Reveal the Dirty Truth to Getting Your Man to Commit hits the stores in paperback on February 7th, a glowing endorsement from Hilary Swank will adorn the back cover.

Better or worse than being blurbed by James Frey?

The words belong to his real estate broker, Suzanne AasboofTradewinds Real Estate, but they may as well have come out of the mouth of Mr. Kirsh-enbaum,39,whothrows around phrases like "ahead of the curve" when describing Quiogue, a tiny hamlet between Quogue and West Hampton Beach where he bought a two-acre estate in November.

Continuing with his pitch for the less famous Hamptons, Mr. Kirshenbaum,co-chairman of Kirshenbaum Bond & Partners, said he stopped renting summer homes in Amagansett two years ago, when he took a place in Quogue. "I know a lot of young couples who have children and want to vacation in the Hamptons," he said, "but don't necessarily want to spend five or six hours in a car."

When they decided to buy a place, Mr. Kirshenbaum said, he and his wife Dana, who have five-month-old twins–a son and a daughter–looked at about 100 houses. They made an offer for just under the asking price of $1.85 million last August on the Homens Road home of June Clemens Ewing, who passed away last year. The deal closed earlier this month.

Built in 1911, the 2,200-square-foot main house has three stories and six bedrooms, beamed ceilings, brick patios, two fireplaces and a turreted tower. Across two acres of property there's also a guest cottage with a fireplace, a barn and apple, walnut, pear and cherry trees. The couple plans to install a pool as part of their $1 million renovations of the house, which was in shabby condition. Ms. Ewing's sister still lives across the street.

Heading west is a trend in the Hamptons, according to Mr. Kirshenbaum. "The most amazing thing right now is that so many people I know are trying to get into the area," Mr. Kirshenbaum said of Quiogue.

"My feeling was that there would be an exodus of people moving west," said one 32-year-old married financial analyst who bought a $1.3 million house in nearby Quogue last January. He is currently in the process of tearing down the existing house and building another one. "The drive [to East Hampton] is just unbearable–plus once you're out there, it is the same people you see everyday in the city. In the worst conditions, the drive to Quogue is an hour and 45 minutes."

Another couple, Ken Cohen, a health-care consultant, and his wife, Marjorie Cohen, who works as a fashion sales consultant, bought a 1920's home for just over $650,000 in Quogue last January and moved in on June 24. "We looked in North Haven, Sag Harbor, all along the north coast of the South Fork," Mr. Cohen said. But Quogue "is a lot closer to New York, where we have to commute to work, and it has a reasonable tax base, and it's quiet, and we're close to the beaches here."

Prices are lower, too, according to Norma Reynolds, who owns a realty company in West Hampton Beach where, she said, "buyers can get the house they wanted."

"I have had a few customers buy in Bellport instead of the Hamptons and in Westhampton and Quogue, but I've also had customers buy on the North Fork, in upstate New York and in Connecticut," said Paige St. John of Cook Pony Farm Realty in Bridgehampton, closer to the red-hot center of the Hamptons, East Hampton.

"There are always people who want to come to the Hamptons. I've been out here since I was born, and there are always people saying the place is ruined and leaving," said Ms. St. John. "They are just replaced by a new set of people, some of whom get sick of the whole scene and leave and are then replaced by a whole other group of people again. And the cycle goes on and on."

WEST VILLAGE

IT HAPPENED ONE FALL: $12 MILLION TOWNHOUSE SETS RECORD DOWNTOWN It has happened: A townhouse in the West Village sold in late October for $12 million–a record high for a house in the neighborhood.

Even at almost $1 million below the asking price, the amount paid for 12 St. Lukes Place, a four-story brownstone between Hudson Street and Seventh Avenue, shocked neighbors and real estate industry observers. The buyers, according to brokers, are a couple in the financial industry.

Sara Gelbard of the Corcoran Group, the broker representing the seller, confirmed the sale but refused to comment.

Although St. Lukes Place is one of the most desired streets in the neighborhood–Robert De Niro has a home on the block, and Linda Ellerbee lives there–brokers were still surprised at the hefty asking price when the building first came on the market for $12.995 million last June, especially since the sellers had paid a mere $2.9 million for the house five years ago.

"It's beautifully renovated," said one broker at the time, "but still, that's quite a jump."

The house, part of a row of 12 landmarked houses that were all built between 1852 and 1853, is located across the street from the James J. Walker Park, named for the Mayor who used to live in No. 6. The houses are especially wide for the Village–12 St. Lukes Place is 21 feet wide–and most were built with "triple parlors," three rooms on the parlor floor.

In addition to a two-story, sky-lit former artist's studio out back, the house has a small garden and a large deck on the third floor. There are also two bedrooms and two baths each on the third and fourth floors. On the garden level, there's a fifth bedroom and bath that has been variously used as a maid's room and an office.

Do I hear $13 million?

UPPER EAST SIDE

1141 Park Avenue

Four-and-a-half-story, 5,800-square-foot townhouse.

Asking: $4.4 million. Selling: $3.6 million.

Time on the market: 15 months.

NOBODY EVER KICKS THE KIDS OUT ANYMORE The parents of two college-age kids who bought this turn-of-the-century limestone and brick building on the northeast corner of East 91st Street probably thought the purchase was their greatest idea ever: Buy a hacked-up tenement, gut the whole thing (including the two doctors' office duplexes as soon as their leases expire) and turn the five-unit building into a townhouse with a lobby to try to convince the kids that it is really three separate residences. The kids will be seduced by rent-free living in New York, and you get to keep them under your roof–a Park Avenue address, no less. The "great idea" was brokered by three Douglas Elliman brokers: Nancy Weaver and Tom Wexler, who sold this house to the seller almost 20 years ago, and Patricia Warburg Cliff, who brought the family over from another townhouse on East 78th Street.

UPPER WEST SIDE

2000 Broadway (Copley Condominium)

Two-bed, two-bath, 1,265-square-foot condo.

Asking: $875,000. Selling: $858,000.

Charges: $963. Taxes: $808.

Time on the market: five weeks.

ONE MORE FORTUNE HUNTER A single guy from California was coming to seek his fortune in New York–in finance, of course. A modern man, he started searching for apartments on the Internet, where he came across an apartment for sale with Naomi Davis of Coldwell Banker Hunt Kennedy. That condo had already been sold, but the two hit it off, and the Californian asked Ms. Davis to help him find a two-bedroom apartment. The place had to be pet friendly (the client came with a schnauzer). They looked at several condominiums before choosing this one: a two-bedroom apartment being sold by an estate at the Copley Condominium, a 28-story building on Broadway and 68th Street. The Copley, which was completed in 1986, has a doorman, concierge, gym and swimming pool. The executors of the estate were initially asking $925,000 for the apartment but reduced that to $875,000 when no one made any offers. They then accepted almost $20,000 less than that.

CHELSEA

440 West 23rd Street

Two-bed, two-bath, 1,450-square-foot co-op.

Asking: $1.175 million. Selling: $1.175 million.

Charges: $1,076; 17 percent tax deductible.

Time on the market: one month.

THE PARISIAN INTERPRETATION OF T.L.C. This duplex in an 1850's row house between Ninth and 10th avenues has 12-foot-high ceilings, two fireplaces and a balcony off the back. Add to that the T.L.C of two creative types (one an architectural designer), and you get an elegant prewar space with French doors separating the rooms, crown moldings and a chandelier in the bedroom. "You didn't feel like you were in New York," said the pair's broker, Susan Wires of Stribling Wells & Gay. Enter a Parisian woman who won out over four other interested buyers. She had tried for a few months to buy an apartment in this group of townhouses–described in the American Institute of Architects Guide to New York City as "a phalanx of Anglo-Italianate brownstones opposite the bulk of London Terrace." She was "very qualified"–i.e., rich–"and we thought she would be the best for the building," said Ms. Wires. The deal closed in mid-October.