Watch VoirFilms. Playboy, a brand now synonymous with sex, was launched by Hugh Hefner in the 1950s in Chicago. Hefner bought the iconic Playboy mansion in Chicago’s Gold Coast where his raucous parties became the stuff of legend. He also opened the first of 30 Playboy clubs in Chicago, outfitting cocktail waitresses in heels and bunny tails. Audio-narrated descriptions of key visual elements are available.