This Month in Playboy History spotlights the magazine that helped redefine postwar American culture, fearlessly pushing boundaries around sexuality, censorship, and personal freedom.

Each short episode revisits a single calendar month across three different years, weaving together headline-making moments from founder Hugh Hefner’s world, provocative interviews with cultural icons like Bob Dylan and Steve Jobs, and the unforgettable Playmates who became part of the magazine’s enduring legacy.