21 Club — 21 West 52nd Street
The swanky 21 Club was even swanky back in 1929, when it was one of the most high-profile speakeasy joints in the country, catering to Hemingway, Bogart, Sinatra and other Hollywood types. A 1930 raid prompted the construction of a secret passageway to a hidden door to an adjacent cellar, where the club’s booze was stashed. When cops raided, the bartender would simply press a button, flipping the bar’s shelves upside down and smashing the bottles of booze directly into the NYC sewer system.
300 Club — 151 West 54th Street
Actress and spitfire Texas Guinan would greet her customers, “Hello suckers,” as they poured in droves to the speakeasies where she emceed. Finally opening her own place, the 300 Club had 40 sexy fan dancers who would rub up against illegal imbibers. When busted by the cops, she’d say patrons brought their own liquor with them, and that her girls simply had to dance so close to the customers because the club was “too small.”
El Fey Club — 123 West 45th Street
Hell’s Kitchen mobster Larry Fay ran a bootlegging racket, running whiskey from Canada to New York in his fleet of city cabs. He opened El Fey on 45th Street to help unload the booze fresh from the north and hired once-customer Guinan as the boisterous hostess of the club.
Landmark Tavern – 626 11th Avenue
Landmark Tavern opened its doors in 1868, long before Prohibition, on what was then the waterfront of the Hudson. Founded by Patrick Henry Carley and his wife, who lived on the second and third floors with their children, it was originally an Irish saloon. Since Prohibition killed the economy of many drinking establishments, they had to transform the third floor into a speakeasy in order to support their family. The bar was never raided and has been open consistently since 1868.
Club Intime — 205 West 54th Street
The Midtown outpost of Flute Bar and Lounge was once Club Intime, a speakeasy stop for society men who frequented Polly Adler’s brothel nearby. Another Texas Guinan joint, the bar celebrates its history with a hot-jazz party the last Saturday of every month, inviting guests to dress in their old timey best and sip champagne in the same alcoves where Guinan’s patrons did.
Chumley’s — 86 Bedford Street
It was a tragedy when Chumley’s closed its doors in 2007 to fix a collapsed chimney, then never re-opened (or will it still?). The cozy speakeasy opened in 1922 at 86 Bedford — which is fabled to have coined the restaurant term to “86” something, or get rid of it. When warned of a police raid, the Chumley’s staff were told to send their customers out the Bedford Street door. Somehow, the cops would always enter through the Pamela Court entrance, allowing the customers to escape without being seen.
The Stork Club — East 53rd Street
The Stork was always a celebrity hot spot — before, during and after Prohibition. Gossip columnist Walter Winchell (1930’s answer to TMZ) called it New York’s New Yorkiest place — and based all of his newspaper columns and radio broadcasts on gossip he overheard at his private Table 50.
The Cotton Club — 644 Lenox Avenue
Despite being home to the greatest black entertainers of the era, including Lena Horne, Count Basie, Ella Fitzgerald, Louis Armstrong, and Duke Ellington (who was the house band during Prohibition), Harlem’s Cotton Club was strictly whites-only — and also strictly upheld a standard of extreme racism. Its owner, bootlegging gangster Owney Madden, ran the club from Sing Sing as a place to unload his bootleg beer, attracting celebs and locals who wanted in on the best jazz performances in New York.
Casa Blanca — 33 West 56th Street
El Fey owner Larry Fay’s other venture, the Casa Blanca Club, was a haven for gangsters that started to lose popularity in 1931. On New Year’s Day in 1932, Fay announced to his staff that they’d be getting a 30% pay cut. The doorman wasn’t too pleased, and came at Fay that night with a gun, shooting him dead and putting a permanent end to Fay’s bootlegging and racketeering career.
Connie’s Inn – 7th Avenue and West 131st Street
Connie’s gave the Cotton Club a run for their money, booking jazz acts like Louis Armstrong, Fats Waller, and Fletcher Henderson — the only difference was that Connie’s let the musicians design their own shows. They shut down as soon as Prohibition ended, seeing no point or fun in legally selling booze.