Hugh Hefner, who died on Wednesday, September 27, at age 91, was always surrounded by beautiful women. The Playboy founder married three times, but was mostly recognized for having multiple live-in girlfriends at the Playboy Mansion.
Though the media mogul tried his hand at marriage, his first two — to his childhood sweetheart Mildred Williams in 1949 to 1959, and Kimberley Conrad from 1989 to 2010 — didn’t last. He is survived by his third wife, Crystal Harris, as well as four adult children from his two previous marriages.
Scroll through to look back at the icon’s greatest loves.