21 Club

The 21 Club's roots trace to the Greenwich Village speakeasy 'The Red Head', opened by Jack Kriendler and Charlie Berns in the early 1920s. After several relocations, they established a speakeasy at 42 West 49th Street, which they called 'The Fronton'. In 1929, they purchased the townhouse at 21 West 52nd Street, renaming it '21'. To evade police raids, the owners installed a secret wine cellar behind a brick wall, accessible by a hidden door that swung open when a specific bottle was pulled from a rack. The cellar could be drained of its contents by a lever that dumped bottles into a sub-basement, and the entire system was designed to be dismantled quickly. The speakeasy became a favorite of celebrities, politicians, and writers, including Ernest Hemingway, who reportedly drank there, and the fictional character Jay Gatsby is said to have been inspired by its atmosphere.

After Prohibition ended in 1933, '21' transitioned into a legitimate restaurant, retaining its exclusive cachet. The facade became famous for its collection of cast-iron jockey statues, painted in the racing colors of prominent patrons, including the Vanderbilts, the Whitneys, and the Rockefellers. The statues, which number 33, were originally used as a marker for the speakeasy's location; a jockey with a raised arm signaled that the establishment was open for business. Over the decades, the restaurant became a power-dining venue, hosting presidents from Franklin D. Roosevelt to Donald Trump, and was a backdrop for numerous films, including 'The Godfather' (1972) and 'Wall Street' (1987). The restaurant also maintained a private dining room on the second floor, known as the 'Punch Room', which was used for secret meetings and celebrity gatherings.

The menu at '21' was classic American, featuring dishes like chicken hash, steak tartare, and the signature '21' burger, which was served with a secret sauce. The restaurant was also known for its extensive wine list, which at its peak included over 50,000 bottles stored in the original Prohibition-era cellar. The wine cellar was a point of pride, and the restaurant's sommeliers were respected for their expertise. In 2005, '21' earned two Michelin stars, a recognition it held until 2012.¹ The restaurant also had a tradition of serving a complimentary glass of champagne to female guests, a practice that was discontinued in the 1990s.

In 1985, the Kriendler family sold '21' to General Mills, which later sold it to the Riese Organization in 1995. The restaurant changed hands several times over the following decades, with ownership by the Orient-Express Hotels (now Belmond) from 2006 to 2015, and then by a group of investors led by Aby Rosen. Despite its storied history, '21' struggled to adapt to changing dining trends and the rise of casual dining. The COVID-19 pandemic dealt a severe blow, and the restaurant closed temporarily in 2020. It reopened briefly in 2021 but never regained its former glory. In 2025, the owners announced the permanent closure, citing rising costs and a shift in consumer preferences.² The building, which is a New York City landmark, was sold for redevelopment, though the facade and jockey statues are preserved.

Beyond its famous patrons, '21' had several obscure features. The restaurant had a secret 'hidden' room behind a bookcase in the bar, used for high-stakes poker games and private parties. The wine cellar's emergency drain system was so effective that during a 1930 raid, agents found no evidence of alcohol. The jockey statues were not always on the facade; they were originally placed on the roof of the speakeasy to signal its location. The restaurant also had a tradition of serving a '21' cocktail, a blend of rum, gin, and fruit juices, which was invented by the bartender in the 1930s. Additionally, the restaurant's phone number, 'PLaza 1-2100', was one of the most famous in New York, and the restaurant was known for its policy of refusing service to anyone wearing a hat, a rule that was famously enforced on Frank Sinatra in the 1950s.

Speakeasy

An illicit establishment that sold alcoholic beverages during the Prohibition era in the United States (1920–1933).

Prohibition

The nationwide constitutional ban on the production, importation, transportation, and sale of alcoholic beverages in the U.S. from 1920 to 1933.

Jockey statues

Cast-iron statues of horse jockeys, painted in racing colors, that adorned the facade of the 21 Club.

Michelin stars

A rating system used by the Michelin Guide to grade restaurants on quality, with one to three stars awarded.