The founder and chief creative officer of Playboy Enterprises infamously dated blonde after blonde, most notoriously courting the cast members of the short-lived reality series The Girls Next Door. Even though he certainly had his fill of bombshells — previously admitting to sleeping with "more than" 1,000 women — Hef maintained that he always stayed faithful during the multiple times he was married.
"There were chunks of my life when I was married, and when I was married I never cheated," he has said. "But I made up for it when I wasn't married. You have to keep your hand in."
Hugh with Kendra Wilkinson, Bridget Marquardt, and Holly Madison.
Hef was a distinguished polygamist with a reported net worth of $43 million and famously welcomed his multiple girlfriends to live in his house, also known as the Playboy Mansion. Though he never proposed to his "No. 1 girlfriend" of seven years, Holly Madison — who has since outed many of the Mansion's secrets (like what sex with Hef was like and how she was offered prescription drugs!) — Hugh tied the knot with Crystal Harris in 2012. At the time, he was 86 and Crystal was 26. At the time of his death, they were still together and keeping a low profile.
Scroll through the gallery to see what Hugh Hefner's exes look like then and now!