Hugh Hefner

Hugh Hefner started his magazine Playboy in 1953, a mainstream lifestyle publication that celebrated sex at a time when Americans were none too willing to talk about such things in public. The first issue included a now-famous calendar photo of Marilyn Monroe and quickly sold out. Playboy, not without controversy, became a smashing success, known for its high quality of writing as well as its regular photos of naked women. Hefner also opened nightclubs in the 1960s and '70s, featuring scantily clad women known as "Bunnies." He even had a TV show, Playboy's Penthouse, in the early days of cable television. He had a stroke in 1985 that slowed his swinging lifestyle, and in 1988 he turned over business operations to his daughter, Christie. After nearly a decade of being a husband and father, Hef bounced back in the late '90s as a swinging senior citizen, once again enjoying the limelight and boasting a harem of much younger girlfriends.