21 West 52nd St
Guarded by lawn jockeys on the balcony above its entrance, 21 Club is an iconic New York restaurant which started as a Prohibition-Era speakeasy.
The 21 Club is a “jacket required, jeans not permitted” kind of place with a very expensive menu and an intimidating list of regulars. The assigned celebrity table seating-lists have included Dorothy Parker at table #6, Ernest Hemingway at table #7 (also assigned to Richard Nixon and Henry Kissinger), George Clooney at #8, and none other than Frank Sinatra at #14.
The 21 Club opened on January 1, 1930, with one momentous celebration. The club founders and owners, cousins Jack and Charlie, got the idea that operating speakeasies during the Prohibition was much more profitable and fun than finishing college. They were in the speakeasy business since 1922, and in 1929 opened their popular Puncheon Club on West 49th Street.
However, the Puncheon Club would not last long, as the location was claimed for the Rockefeller Center. Jack and Charlie threw a spectacular gala demolition party where decked out and highly inebriated guests destroyed the club, picking up its iron front gate and carrying it over to the new location at 21 52nd Street. This iron gate is still there.
Once, when the restaurant was raided by the police, the waitstaff swiftly dumped all the alcohol. However, Jack and Charlie ran a classy joint and resented the loss of expensive libations. To solve the problem, they installed a clever security system with false walls, hidden doorways, and secret stairways, ensuring that the police would not discover the treasure of a secret wine cellar housing 2,000 cases of wine. The cellar also held the private collections of many celebrity patrons, such as Presidents Gerald Ford and Richard Nixon, Elizabeth Taylor, Sophia Loren, Mae West, Eva Gabor, and Aristotle Onassis.
Technically, the wine cellar was not even located in the 21 Club, but rather in the basement of the neighboring house #19. In case the police inquired, the 21 Club could honestly profess that there was no alcohol stored on the premises. The bar shelves were designed to collapse, sending the bottles safely down a shaft.
The club’s entrance is famously adorned with lawn jockey figures. The first one was a gift from a patron in the early 1930s. Not to be outdone, the others presented the 21 Club with jockeys painted to represent the racing colors of the stables they owned.
Along with movie stars and the biggest celebrities, every sitting president since FDR has dined in the 21 Club – except for George W. Bush (he visited there before he became president) and Barack Obama. The Club is mentioned or featured in such movie classics as Rear Window, North by Northwest, Breakfast at Tiffany’s, All About Eve, and Manhattan Murder Mystery, among many others.
Visit it not for the food but out of fear that if it closes or is remodeled, you’ll always regret having never visited the 21 Club.