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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.