Hefner helped usher in the 1960s sexual revolution with his groundbreaking magazine, around which he built a multi-million-dollar business empire.
He began his career working as a copywriter for Esquire, before founding Playboy in 1953 with the help of several investors including his mother, who loaned him $1,000, according to a New York Times profile.
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The first issue of the magazine featured a nude cover of Marilyn Monroe photographed four years before, and sold over 50,000 copies, according to Playboy Enterprises. Hefner would famously go on to purchase the burial crypt next to Monroe’s, located in Los Angeles, for $75,000.
In 1959, Hefner began exploring the burgeoning television market by hosting Playboy’s Penthouse, a variety show set in a bachelor pad.
Over the years, Hefner came to be renowned for his swinging lifestyle, and his habit of keeping a harem of young women at his legendary Playboy Mansion.
He was married three times — in 1949, 1989 and most recently in 2012.
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Hefner said his swinging lifestyle might have been a reaction to growing up in a repressed family where affection was rarely exhibited.
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His so-called stunted childhood led to a multi-million-dollar enterprise that centered on naked women but also espoused Hefner’s “Playboy philosophy” based on romance, style and the casting off of mainstream mores.
That philosophy came to life at the legendary parties in his mansions — first in his native Chicago, then in Los Angeles’ exclusive Holmby Hills neighborhood — where legions of male celebrities swarmed to mingle with beautiful young women.
— With files from Reuters