The Playboy Club was initially a chain of nightclubs and resorts owned and operated by Playboy Enterprises. The first Playboy Club opened in Chicago in 1960. Each club generally featured a Living Room, a Playmate Bar, a Dining Room, and a Club Room. Members and their guests were served food and drinks by Playboy Bunnies, some of whom were featured in Playboy magazine. The clubs offered name entertainers and comedians in the Club Rooms, and local musicians and the occasional close-up magician in the Living Rooms. Starting with the London and Jamaica club locations, the Playboy Club became international in scope.

A Playboy Bunny is a cocktail waitress who works at a Playboy Club and selected through standardized training. Their costumes were made up of lingerie, inspired by the tuxedo-wearing Playboy rabbit mascot. This costume consisted of a strapless corset teddy, bunny ears, black sheer-to-waist pantyhose, a bow tie, a collar, cuffs and a fluffy cottontail. In more recent Playboy Clubs, such as Sin City that was re-opened in 2006, Playboy bunnies wore slightly altered costumes that were based on the original bunny suit.