This Is Café Society?

At around 11:30 last Saturday night, two men of equally modest stature—one in a gray suit, the other in jeans and a worn jacket—were enjoying a cigarette on the corner of Bank Street and Waverly Place.

The better-dressed man was the actor Sean Penn. He was pointing at something to do with the upper reaches of a townhouse across the street. His companion, Pearl Jam lead singer Eddie Vedder, looked upward, his face peaking out from a tangle of rangy locks. He nodded, seemingly in agreement with what Mr. Penn had said. As this meeting of two great minds transpired, two photographers, standing only feet away, were idly snapping photograph after identical photograph.

Then a third, taller man approached—prompting the lensmen to scramble around for the perfect position.

“Hey, fellas, can we get a group shot?” asked one of the paparazzi. He spoke in a foreign accent.

“O.K., just one and then you’ll leave, right?” said the actor Tim Robbins, as he and his two friends reluctantly, if placidly, succumbed. “I feel like I’m at a premiere,” Mr. Robbins said. “We’re out on the streets.”

Mr. Robbins and his famous friends were not merely out on streets, but on the street in front of the Waverly Inn, a West Village pub recently reborn as the city’s latest clubhouse to the rich and famous under the direction of its host-with-the-mostest, Vanity Fair editor Graydon Carter.

In many respects, dining at the Waverly—as well as huffing down a postprandial fag outside—is very much like being at a premiere. The crowd within the small, dimly lit restaurant on Saturday night would have trumped many a film premiere in terms of celebrity wattage. Adjacent to Messrs. Penn, Robbins and Vedder’s table was Mr. Penn’s 21 Grams co-star, Naomi Watts, dining with a gaggle of girlfriends. Across from the lovely ladies was brooding actor Jason Patric, elbows bent on a two-top, biceps busting out of a blue T-shirt.

Toward the back of the restaurant, in the big booths adjacent the bathrooms—but safely before the garden area, dubbed “Siberia”—sat the likes of rock star Lenny Kravitz, rap mogul Russell Simmons and celebrity photographer Sante D’Orazio.

And shadowing them all was the Edward Sorel mural, commissioned by Mr. Carter and featuring caricatures of Anaïs Nin, e.e. cummings, Jackson Pollock, Bob Dylan, William S. Burroughs, Eugene O’Neill, and others. Mr. Sorel said he charged Mr. Carter the “very cheap” price of $50,000 for the mural. “The only change Graydon made was that he had me take him out of it,” he said. “I had drawn him as a bird with a martini.”

Mr. Sorel added, “Sometimes, when I go there, I am the only person I don’t know.”

New York has a long, celebrated history as a town of fashionable, exclusive, club-like restaurants. A new one opens every season, just as another eats it. But rarely does a restaurant come along that captures the zeitgeist so much that its luminaries are helpless to resist its allure. Rarer still is the restaurant that manages to hold onto that sense of headiness and relevance for a long period of time. One thinks of Elaine’s, the Upper East Side literary saloon that Elaine Kaufman opened in 1964. And one thinks of Mortimer’s, which until it closed in 1998 served as the embattled last holdout of Upper East Side society, with its soigné owner, Glenn Birnbaum, presiding over a roomful of pulled faces and locked jaws. Even if you never set foot in the place—out of disgust or fear of being turned away—its very existence said something naughty and wonderful about New York. Likewise, even if you never snorted coke in the bathroom at Odeon with Jay McInerney and Bret Easton Ellis, or ate flank steaks with made guys at Mafia and movie-star hangout Columbus, well, it was nice to know someone was. (Now all you get is trust-fund twinks who’ve never read an entire book dancing on tables at Bungalow 8.)

While getting a table at Mortimer’s depended more on blue blood than blind ambition—though blond ambition was known to work on occasion—you didn’t have to be famous or even super-wealthy to dine there. The same goes for Elaine’s: Nobodies may not get the good tables, but they do get served. And if a nobody keeps coming back and is polite, after a few years, that nobody becomes somebody, if only within Elaine’s. And as they walk out the door after dinner—which always seems to cost $200, no matter what they eat and drink—they feel like a million bucks.

It’s an open question whether such big-hearted democracy will prevail at the Waverly Inn. Just a few months into its “soft” launch—the restaurant is still not officially open—Mr. Carter’s baby has earned buzz and clientele and, yes, the inevitable comparisons to Elaine’s.

“What you felt walkin’ in there,” recalled publicist Bobby Zarem of a recent trip to the Waverly, “with all the buzz and the excitement, and knowing there were people in there who were prominent and successful—that was the feeling you’d get at Elaine’s 40 years ago.”

He was speaking to The Observer from a table at Elaine’s. The restaurant has seen enough action over the years to provide fodder for entire books, but Elaine’s isn’t history yet. The clubby New York intelligentsia atmosphere that the waitress turned restaurateur created during the Lyndon Johnson years is still going, if at a more measured pace. And Elaine’s remains the context against which Mr. Carter’s new venture downtown must be judged.

Longtime social observers are already drawing distinctions. Of Elaine’s, the writer Gay Talese said, “It’s more sophisticated, in the sense that it isn’t always famous people who have famous faces—there are famous people who don’t have famous faces.”

At least in some respects, Elaine’s was part of Mr. Carter’s inspiration.

“Graydon liked the lighting here, so he said he was going to use it downtown,” said Ms. Kaufman, who was seated a few tables down from her wiry-haired friend, Mr. Zarem. She also wasn’t giving up any sex-appeal ground to the Waverly, gesturing toward one table and saying, “We got Felicity Kendal there, who has the best ass in London.”

“New York’s always had club-like restaurants, whether you’re talking about ‘21,’ the Grill Room, or Michael’s, or Elaine’s,” said the writer Michael Gross, who last visited the Waverly on March 11. Sunday appears to be the Waverly’s one slow night; Mr. Gross had only Calvin Klein and Anne Hathaway to rub shoulders with.

“Elaine’s was the 60’s, Max’s Kansas City was the 70’s, Odeon was the 80’s, Da Silvano was the 90’s—maybe the Waverly Inn is the oughts,” Mr. Gross added.

Mr. Carter’s friends confirm that such a notion would be the sweetest of music to the editor’s ears.

“He loves having this restaurant; he loves being a host,” said the writer Fran Lebowitz. “For his birthday, I gave him a biography, Toots Shor, and his eyes lit up. I think he’s hoping that nickname will catch on.” (Ms. Lebowitz allowed that she herself does not call Mr. Carter “Toots.”)

“Even before we started Spy, he’s always wanted to start a clubhouse,” said Mr. Carter’s friend and co-founder at Spy magazine, Kurt Andersen. “We’d be walking around Time Square, and he’d look up at different buildings and say, ‘Well, that could be a clubhouse there, and that could be clubhouse there.’”

While Mr. Andersen asserted that his friend had "poured much of his heart and soul" into to the Wavely, it is unlikely that Mr. Carter will have the time and energy to inadopt a cozy management style similar to Ms. Kaufman’s, who is known as "Mama" to regulars.

“I don’t think anybody is as involved at the Waverly—to come over to Sean Penn’s table—and he’s not overseeing and looking around each table and each person and thinking, like Elaine does, you know, who should meet whom and what,” said Mr. Zarem.

That, of course, is Ms. Kaufman’s special gift. “[New York Post editor] Col Allan said he was down there [at the Waverly], and he saw Gwen Paltrow, and he saw McEnroe and all that,” Ms. Kaufman said. “I said, ‘Oh, wonderful—sure, it’s a good place, so that’s where they go now. They used to come here, too,’ I said. ‘But did they talk to you? Did you have a conversation?’ He says, ‘No.’ I said, ‘Here, you would talk to them. Here, everybody’s talking to each other.’”

The two scene-setters’ management styles also part company on the issue of just who “everybody” should be. While Ms. Kaufman seems to eventually open her arms to anyone with decent manners and an inquisitive mind, Mr. Carter’s rule of thumb seems to be simple: The good tables—those in the main dining room—are reserved for his friends, the very famous and the very rich.

The result tends to be an elitist though, at same time, incredibly desultory bag of nuts in the precious dining room—a room high on neck-craning and low on table-hopping.

“It’s more a place to see people than to have lengthy, great conversations with people,” said Mr. Zarem.

“A restaurant that’s filled with movie stars really becomes a movie set,” noted Mr. Talese, who has written at length about New York restaurants and said he was eager to sample the Waverly.

Mr. Zarem recalled that on a recent visit to the Waverly with his actor friends Liev Schreiber and Naomi Watts, Grove/Atlantic publisher Morgan Entrekin was at the neighboring table with the novelist Richard Ford. He said he didn’t recognize anyone else in the room. “Then, as we were leaving, the photographers were roaming around somebody,” he said, “and I didn’t know who the fuck it was, but it was Jennifer Aniston.”

“He’s selling fame, the great narcotic of the century,” said Mr. Talese. “A Hollywood crowd has an appeal that is very commercial. It gives an aura of status, an appeal. People have always had a star-gazing sensibility. Graydon Carter is probably the most successful editor going right now, and the Waverly seems to have a bit of that Annie Leibovitz look.”

Of course, the crowd that Ms. Kaufman appeals to—and who have remained loyal for so many years—has always had a kind of wolfish, aftershave-and-Amaretto glamour: sports writers and TV news reporters and B- and C-list actors. “Elaine’s was never Hollywood—in fact, it was begrudgingly even actorish,” said Mr. Talese, who still eats at Elaine’s on an almost weekly basis. “It’s always been a place for those who have indulged in the written word—that is to say, the solitary worker …. It was the first time that there was a restaurant for writers.”

And while the once ubiquitous after-dinner cigars have vanished from Elaine’s thanks to Mayor Michael Bloomberg’s smoking ban, Mr. Carter continuously puffs away on a cigarette when he’s in his restaurant. Other diners at the Waverly only light up when they see Mr. Carter doing so, as if on cue.

For Mr. Zarem, the success of the Waverly will live and die on the wings of Mr. Carter’s silver locks.

“Graydon has innumerable friends, people that he works closely with, that are high-profile and respect and admire him,” he said. “Also, he lives two houses away, so the Waverly’s here to stay—unlike all the other places that have come and gone.”

“What it is about the Waverly,” said Mr. Talese, “is that it’s the first time that a magazine editor—well, in a sense, he’s the star. He’s a kingmaker or a queen-maker.” He added, “A restaurant that has among its clientele many beautiful women is not going to have to depend on the chef as much …. [New York Times restaurant critic] Frank Bruni is not going to make or break that place. That’s power. It’s ‘star’-proof.”

“I go there because Graydon is a friend,” said Ms. Lebowitz. She added: “I’m happy that his restaurant has delicious biscuits.”

“I think people will continue to go there for the food,” offered Mr. Andersen.

And maybe the sing-alongs.

“About two weeks ago, my fiancée, some friends and I were stupidly singing E.L.O. and Cat Stevens songs—not quietly—at one of the middle-zone dining tables,” recalled BlackBook magazine editor Steve Garbarino. “Ellen Barkin and her group across from us joined in with equally dorky but fun fervor, shouting requests. It’s sounds pretty corny, but it was a good ‘moment’ that went on into the night.”

“The secret of longevity is to know what mixes,” said Elaine Kaufman. “That doesn’t change. You have to have a sense of these things.”

About the Waverly, she added, “It’s a momentary thing; he’s having a good time. And Graydon is the best—he’s a sweetheart. Let him enjoy himself.” This Is Café Society?