Before his affinity for blondes, Hef went for this brunette bunny; they even lived together from 1969 to 1976.
After Barbi, Hef dated former schoolteacher turned centerfold Sondra.
Shanon and Hef dated briefly before she moved in with Gene Simmons in 1985, whom she's been with ever since!
Hef married second wife Kimberly in 1989, the same year she became Playmate of the Year. They have two sons together and didn't finalize their divorce until 2010.
Brande was one of the many Playmates Hef dated in the late '90s. She went on to marry a former NFL linebacker and is a mom now.
Hef and his three live-in girlfriends Holly Madison, Bridget Marquardt, and Kendra Wilkinson starred in reality show The Girls Next Door from 2005 until 2008, when all three left the mansion.
Out of the three girlfriends Hef dated during that time, Holly was clearly his main squeeze, but she left with the others in 2008 and soon after started dating illusionist Criss Angel. Although technically not a Playboy Playmate, she did appear nude in the magazine.
The sixth season of The Girls Next Door featured 19-year-old twins Kristina and Karissa and 23-year-old Crystal Harris. The twin Playmates left Hef in 2010.