Jack and Charlie's "21," date unknown

The story of the bar that ended up here at 21 West 52nd Street began downtown. Cousins Jack Kriendler and Charlie Berns opened a speakeasy called the Red Head on East 4th Street in 1922. Jack and Charlie's venture moved to 88 Washington Place (it was called the Fronton here) and then 42 West 49th Street (called the Puncheon Club here). The Puncheon Club became one of the most popular speakeasies in town, with famous actors, artists, and politicians as regulars. They were forced out of their 49th Street digs by the development of Rockefeller Center in the late 1920s.

Reopened as "Jack and Charlie's 21" here circa 1930, the club continued its illicit activities. They had clever ways to avoid detection. If the case of a raid, employees would push a button to enact a system of levers used to tip the shelves of the bar, sweeping the bottles down a chute and into the city's sewer system. After Prohibition ended the venue continued as a bar (legally) and restaurant. Supposedly a number of celebrities and politicians (JFK, Elizabeth Taylor, Sammy Davis, Jr. to name a few) have stored their personal wine collections here. Known today at the 21 Club, the 37 jockeys that line the facade remain (and even got a restoration in 2015).