Hugh Hefner is living the dream of just about every heterosexual teen boy as the face of a groundbreaking adult entertainment empire. But before establishing Playboy magazine, opening the private key clubs, building the over-the-top mansion complete with girl-filled swimming grotto, inspiring a TV show and living 24-7 in silky robes, he was your average unmotivated student with an alleged IQ of 152 and strict Methodist parents. The founder of a high school newspaper served in the Army during World War II, attended the Chicago Art Institute and earned a psychology degree at University of Illinois at Urbana-Champaign (where he met first wife Mildred Williams). He then worked at Esquire as a promotional copywriter until 1953 when he raised $8,000 to launch Playboy with a nude pic of Marilyn Monroe. It was an instant hit, but workaholic issues and extramarital affairs eventually led the mother of his children Christie and David to leave him in 1959. In the ‘60s heyday, Playboy Enterprises built resorts, started modeling agencies, published books, produced movies and operated a record company. He hosted two weekly talk shows. The Walk of Fame star recipient created the jazz fest in 1978. A stroke in 1985 slowed him down and he married Kimberly Conrad in 1989, a union that produced two sons but ended in 1998. From 2005-09, his multitude of girlfriends was chronicled on E! reality show “The Girls Next Door.” He married one of them, Crystal Harris, when he was 86.
Hugh Hefner Search Results
Love Gets RealUnsolicited advice for eight of reality TV's troubled couples.
Happy for Hef?Holly Madison explains why she has mixed feelings about Hugh Hefner's engagement.
Sam's New NeighborLindsay Lohan moves in next door to Sam Ronson, plus more celeb news in the Shortlist.
Age Not An IssueHugh Hefner's fiance Crystal Harris says she doesn't notice their age difference.
Engagement BlingHugh Hefner's fiance Crystal Harris shows off her new bling.
Nuptial Upset?Is Hef's ex in disbelief over his engagement?
Tying the KnotHugh Hefner and Playmate Crystal Harris are getting hitched!
Playboy Photo SalePlayboy's most iconic photos will be auctioned off this week.
Betty's BachelorsWe try to match Betty White up with Mel Brooks, Bob Barker, Hugh Hefner and more.
'I Do' No. 2Former "Dawson's Creek" star James Van Der Beek marries for the second time.
From Crowd Ignite