On September 26, 2026
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Chicago Stories · S4E5 — The Making of Playboy
Synopsis
Hugh Hefner founded Playboy in the 1950s in Chicago, establishing a brand instantly linked with sensuality. He acquired the famed Playboy Mansion on Chicago’s Gold Coast, transforming it into a legendary locale for lively gatherings. Simultaneously, Hefner opened the first of thirty Playboy Clubs in the city, where cocktail waitresses wore heels and distinctive bunny tails.

