NUMBER OF NOTCHES: “Thousands”
CAREER HIGHLIGHTS: Founded Playboy magazine, romantically involved with many Playmates, including Holly Madison, Bridget Marquardt, Kendra Wilkinson, Barbi Benton, Karen Christy, Willa Ford, Donna Michelle, Marilyn Cole, Patti McGuire, Shannon Tweed, Sondra Theodore, and Carrie Leigh, et al.
Hard to believe but Hugh Hefner was a virgin until after he got out of the Army in his twenties. Naturally, he had to make up for lost time. In
Hef’s Little Black Book, the 83-year-old Playboy founder admitted that he has slept with “thousands of women—and they still like me.” And the women don’t disagree: “Nobody can really let go of him,” one ex confessed. “You can hate him, hate him, hate him, but at the same time you have all these emotional mushy feelings about Hef. That’s why he’s still friends with all of us.”