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
Back TogetherA six-decade age difference and a few insults couldn't keep Hugh Hefner and Crystal Harris apart ...
Them again?Has Hugh Hefner welcomed runaway bride Crystal Harris back into the Playboy mansion?
Golden tweetsBetty White joins the tweeting masses. Plus, more celeb news in the Shortlist.
Failed EngagementA look back at all the lovebirds whose relationships fell flat before making it to the altar.
Child's PlaySee which stars are like Danny Glover's character in "Lethal Weapon" and are too old to be doing what they're doing.
no charges?Marston Hefner won't face charges for allegedly abusing his Playmate girlfriend if he publicly apologizes...
arrestedHugh Hefner's son is arrested for allegedly attacking up his girlfriend, a former Playmate.
Fresh StartAfter a rough 2011, see which stars need a fresh start in 2012.
2011 Love ReportSee who found love and who experienced heartbreak in 2011 ...
Drug problemsCrack and marijuana contributed to Sinead O'Connor's breakup, plus more news in the Shortlist.