Of the many classic eating and drinking institutions in New York City, perhaps none occupies so prominent a place in the popular imagination as the ‘21’ Club. Among the reasons: a speakeasy history, unusual decor, roles in venerable films and a reputation for celebrity clientele—a cache of journalists, theater and Hollywood folk, politicians and industry magnates, the types that would regularly appear on Page Six.
The ‘21’ Club has also managed to remain relevant while retaining its character. It’s a destination for curiosity seekers, traditionalists and historians, an attraction in its own right and also a welcoming place for customers in search of a good meal and properly made cocktail. Read on for our guide to the eatery’s past and present.
When Jack Kriendler and Charlie Berns moved their establishment—which had originally gone by the names of the Red Head and the Fronton when a speakeasy in Greenwich Village—to 42 W. 49th St., they called it the Puncheon. In a bit of foreshadowing, it was nicknamed “42” thanks to its address. At the end of 1929, they moved it to a townhouse at 21 W. 52nd St. and dubbed it Jack and Charlie’s ‘21’, which eventually morphed into the present name.
The “Club” part may give off an air of exclusivity, but the place has never been a private establishment with a membership. You can be forgiven for assuming otherwise. Longtime doorman Shaker Naini, who has been there since 1978, estimates that around 50 percent of the clientele in the old days were regulars (though now says that’s down to 15 or 20 percent). “Everybody knew everybody. Everyone would get the same table [they usually got]—and if they didn’t, they were disappointed.”
The jockey figurines perched along the exterior railing have become so associated with the restaurant that they have been incorporated into its logo, flanking the ‘21’ on the outdoor gas lamp and menus. According to former owner Pete Kriendler’s memoir (Pete took over operating the place after Jack’s death, in 1947), the earliest jockeys were gifts from horse-racing moguls—either Jock Whitney or Alfred Gwynne Vanderbilt II being the first to bequeath one. Whatever the origin, having a colorfully outfitted jockey along the grilled terrace worked as a proud symbol both for the donor’s horse farm and for the restaurant.
The signature look of ‘21’ doesn’t stop at the iron gate, which itself had been transferred from the Puncheon. Model planes, helmets and other curios festoon the ceiling in the Bar Room, which is actually the main dining room. The very first toy hung was from a gift from the head of Imperial Airways (now British Airways), who wanted to impress some investors he was dining with. Not to be outdone, other corporate bigs—first from airline companies, including TWA’s Howard Hughes, and then from every field imaginable—soon followed suit, and the collection built up to cover pretty much every inch of space above the tables. Among the ephemera: a battery-powered Starship Enterprise, a roughly 15-foot commemorative oar from the Henley Regatta, an Air Force One model from President Clinton and a pool cue used in The Hustler that Jackie Gleason swapped for a model train he envied. Regular guests continue to contribute stuff to this day—though, as there’s limited space, the house gets to determine what’s put up.
While the Bar Room remains the place most visitors go to eat lunch or dinner, the first thing you see upon entering the place is Bar ‘21’: it became its own area in 2011. You can lounge in its plush booths without a tie, enjoy an abbreviated menu that includes some versions of what’s available in the main room and sip martinis while gazing at original paintings by Frederic Remington.
Though there’s certainly a lot to see on the main floor, in some ways the highlight of ‘21’ Club is subterranean and hidden—perhaps fitting for a for a place that operated in the Prohibition era. The wine cellar is behind a 2.5-ton stone door that seems to have no natural access; the key is an 18-inch meat skewer that fits into a hole in the wall, a trick that dates back to the days of hiding the goods during Prohibition. Behind the door, a room holds personal bottles that customers have set aside there, many never to be consumed. Among them are bottles belonging to Richard Nixon, Ivan Boesky, LeRoy Neiman and Chelsea Clinton (a gift from Chelsea’s parents in anticipation of her 21st birthday).
Past the shelves, the cellar opens up into a private dining room, the centerpiece of which is a long common table; you can enjoy a private meal for up to 22 guests. Over in the far corner sits a wooden booth with elaborate carving; it was once the preferred seat of Mayor Jimmy Walker, who supposedly brought his mistress here. Note: you can request a tour of the wine cellar when you make a reservation (ask again when you arrive to ensure its availability).
Upstairs at ‘21’ is a more formal space. Used frequently for special events, it’s only open to the public Friday and Saturday evenings and offers a four-course prix-fixe menu. The many oil paintings on its walls herald a hushed atmosphere that’s a contrast to the lively Bar Room below.
The food and drink
The restaurant, headed these days by executive chef Sylvain Delpique, is known for dishes that have been on the menu across decades: steak tartare, chicken hash, chicken paillard, baked Alaska and the ‘21’ burger—which has gone through a number of incarnations but is widely credited with being the first fancy burger in town. These carry on ‘21’s history of luxury American cuisine, which in past menus has highlighted items like green turtle soup and breast of guinea hen. There are lighter, more contemporary touches, like the kale chips that accompany monkfish or the apple and celery in the crab cake. The menu also includes seasonal ingredients like English peas or zucchini blossoms.
The martini and Manhattan are undoubtedly the house drinks here, but the cocktail program isn’t just old school; bartenders make their own syrups and the Paloma is made with scotch bonnet pepper. Kriendler’s book claims the Bloody Mary was a ‘21’ Club invention; that seems rather up in the air, but his mention of the B&B coming from here seems on firmer ground. As for the wine list, its vintages number into the thousands—as do the prices for some of the finer bottles.
The dress code
A longtime holdout for its dress code, ‘21’ required a jacket and tie for men until 2009. This led to the restaurant carrying loaners in case of emergencies, as well as some incidents when customers didn’t wish to comply. According to Naini, “Sometimes we turned away very famous people because of the dress code, like when Burt Lancaster and Better Midler wore jeans.”
A jacket is still required to dine in the Bar Room, and it pays to look nice and avoid garments like jeans and sneakers—but the lounge area is business casual.
- Richard Nixon was a regular at the restaurant (Naini says that after his presidency ended and he lived in New Jersey, Nixon lunched here regularly on Saturdays). He is just one in a procession of presidents to have dined at the establishment since the days of FDR—Barack Obama the exception (George W. Bush came when he was governor of Texas).
- Table 30 is Bogie’s Corner, or the Humphrey Bogart–Lauren Bacall table, and a favorite with customers. The most frequent request is Table 3, where Wall Street’s Gordon Gekko tells Bud Fox to get the steak tartare (Gekko doesn’t eat anything as, according to him, “Lunch is for wimps”), hands him a fat check and welcomes him to big-time investing.
- The restaurant has also featured in All About Eve, Sex and the City, Rear Window and, probably most famous of all, The Sweet Smell of Success.
- Columnist Robert Benchley, a frequent drinking companion of Dorothy Parker, is memorialized by a plaque that says “Robert Benchley–His Corner,” which hangs where he would hold court at Table 3.
- The restaurant incorporates three different buildings—17, 19 and 21 W. 52nd St.—and has expanded multiple times over the years; architects Duggin and Crossman designed all three.
- The ‘21’ Club published The Iron Gate back in 1936. It’s a compendium of drawings and stories by the arts-inclined clientele, with ‘21’ as the subject. One of its pieces had Rube Goldberg illustrating a contraption to get you past the door. These days it’s a bit easier.