On East 59th Street between 5th Avenue and Madison is a nondescript, gray and slightly dour looking building. Nine stories high and alleviated only with a relaxed and charming Italian wine bar occupying half of the ground floor, the building is as anonymous as it is unassuming. But once, Number 5, East 59th street was so exclusive in its glamorous secrecy that entry was only permitted to those holding a particular key. This key was plain except for a silver and black enameled rabbit head on one side, and an individual number on the reverse, next to the initials NY. Long since forgotten, this was once the home to Hugh Hefner’s famed Playboy Club.

Top Places in New York

New York, New York

Nikola Tesla Street Corner

Commemorating the spot where the famous scientist fed his pigeons.

40.7536, -73.9850

Added by Alicia Bones

New York, New York

Pomander Walk

Peek through the gates at this oasis from the city, full of Old English charm.

40.7943, -73.9731

Added by Oliver Hong

New York, New York

Sylvan Terrace

A discreet little stairway on St. Nicholas Avenue leads to a quaint and unexpected cobblestone street of 19th century wooden rowhouses.

40.8349, -73.9399

Added by michelleferlito

See more things to do in New York »

The first Playboy nightclub opened in Chicago in 1960, with New York following in December 1962. At one point, Hefner operated over 40 clubs all over the world, from Michigan to Manila, where entrance could only gained by ownership of a key which cost $25 a year. The owner of the key would approach the doors of Number 5 and hand his key to a bunny girl guarding the entrance. Once inside, the aspiring playboys would find plush, dimly lit Playmate bars, dining rooms, cabarets, and club rooms all patrolled and serviced by the Playboy bunny waitresses.

The Bunny Instruction Manual of 1968, given to all newly hired bunnies revealed, “Playboy Clubs are world famous for their distinctive decor....man-sized drinks and particularly their beautiful bunnies.” Amongst those serving the man-sized drinks in Manhattan were Debbie Harry, Lauren Hutton, and Gloria Steinem.

Working life for a Playboy bunny was governed by strict rules that if broken would lead to instant dismissal. Dates with keyholders were absolutely forbidden, as was chewing gum on duty. Other offenses included “bunny ears not worn in center of head, bent incorrectly” or worse of all “unkempt tail.” 

For some reason the rules were much stricter in New York. The manual specified that “at all clubs, except New York club, bunnies may dance with patrons....provided there is no close physical contact.” While at Playboy clubs all over America, “the twist, watusi, bugaloo, etc. are examples of acceptable dances,” all were forbidden for the hard drinking ad men of Madison Avenue. 

Playboys may have expected the bunnies “to be a beautiful, well-groomed young lady who projects warmth and graciousness at all times” but the nightclubs eventually fell out of favor and began closing in quick succession throughout the 1980s, with the last closing in 1991. Several attempts to open modern version of the nightclubs in Las Vegas, London, and India have met with mixed success. 

The New York Playboy club closed its doors in 1986, bringing to an end the swinging era when most men wore cufflinks and tie clips, and were served man-sized Old Fashioneds by Hefner’s glamorous bunny girls. Provided of course that their iconic rabbit ears were not bent incorrectly.

Update March 2018: The restaurant is gone and the building is up for lease.