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 the social and entertainment pages of publications.
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 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 Gwynn 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.
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.