As the founder and editor-in-chief of Playboy magazine, Hugh Hefner was famous for his many girlfriends , wild parties and controversial lifestyle. Surprisingly though, despite all the women that passed through the Playboy mansion over the years, Hefner was only married three times: first to Mildred Williams between 1949 and 1959, then to Kimberley Conrad between 1989 and 2009, and finally to former Playboy model Crystal Harris, from 2012 until his passing in 2017, per Business Insider. {"@context":"https://schema.

org","@type":"ImageObject","caption":"Crystal Harris Hefner alongside Playboy founder and former husband Hugh Hefner. Photo: @crystalhefner/Instagram","url":"https://cdn.i-scmp.

com/sites/default/files/d8/images/canvas/2024/05/31/d4168da9-5f6c-4c33-92db-f3e246e6a980_7390c88c.jpg"} Crystal Harris Hefner alongside Playboy founder and former husband Hugh Hefner. Photo: @crystalhefner/Instagram Hugh proposed to Crystal in 2010, when she was 23 and he was 83 – yes, they had a 60-year age gap.

And while their marriage might appear to follow a typical gold-digger narrative at first glance, Crystal was actually never in Hugh’s will. In fact, the couple even signed an ironclad prenup, which meant she was unlikely to inherit any of his millions, per Us Weekly. {"@context":"https://schema.

org","@type":"ImageObject","caption":"Crystal Harris poses for The New York Times in January. Photo: @crystalhefner/Instagram","url":"https://cdn.i-scmp.

com/sites/default/files/d8/images/c.