Lifelong ladies man Hugh Hefner finally married Crystal Harris on New Year's Eve. In honor of their recent nuptials, let's take a look at the other ladies in Hef's past.
Playboy founder Hugh Hefner has had countless lovers over the years — some more notable than others. Here's a chronological history of the wives, girlfriends, and Bunnies who found themselves in his bed. Because Hef has never been a one-woman man, there's a lot of overlap.
Image by Dan Kitwood / Getty Images
Mildred Williams (1949-1959)
Hef married his first wife in 1949. Mildred cheated on Hugh while he was in the Army, but she later gave him a free pass for sleeping with other women.
Donna Michelle (c. 1963-1964)
1964's Playmate of the Year Donna Michelle was only 17 when she first posed nude in Playboy. She died in 2004.
Barbi Benton (1969-1976)
Partnered for eight years, Barbi and Hugh met on the set of Playboy After Dark. Hef later said that meeting Barbi was his favorite memory of doing the show.
