Hugh Hefner, who died in September 2018 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 attempts— to childhood sweetheart Mildred Williams from 1949 to 1959, and to Kimberley Conrad from 1989 to 2010 — didn’t last. He is survived by his third wife, Crystal Hefner (née Harris), as well as four adult children from his two previous marriages. (Hugh shared Christie and David with Williams and Marston and Cooper with Conrad.)
Hugh’s love life was the subject of the Girls Next Door reality TV series, which aired on E! from 2006 to 2009. The six-season series primarily highlighted his relationships with the likes of Holly Madison, Bridget Marquardt and Kendra Wilkinson. The final season of the show introduced Crystal, and twins Kristina and Karissa Shannon.
“I’ve been blessed for many, many things but to find true love at this age, at this stage of life, is beyond words,” Hugh previously told E! News in 2014, two years after marrying Crystal. “Things could not be better.”
After the former magazine editor’s death, Crystal exclusively opened up about her loss to Us Weekly.
“It’s been a whirlwind,” Crystal told Us in March 2020. “It’s been trying to find myself. I became someone else’s identity for 10 years. I’m finding my own identity and place in the world. It’s scary. … I’ve been doing a lot of traveling and seeing the world. I didn’t do much of that living at the house. Hef and I were just homebodies. He didn’t like me traveling. I guess I’m making up for lost time.”
Hugh’s past relationships made headlines once again after the January 2022 premiere of the A&E docuseries Secrets of Playboy. The Vegas Diaries author and other former Playmates came forward with allegations about the Illinois native’s inappropriate behavior during his mansion residency.
“We sign our names to support Hugh M. Hefner. From all we know of Hef, he was a person of upstanding character, exceptional kindness and dedication to free thought,” a collective of former Playboy employees and models wrote in a joint statement, obtained by Us Weekly, in February 2022. “He demonstrated a commitment to living an honest life beyond everything else. Our time within Hugh Hefner’s Playboy and the organization’s subsidiaries remains a period all of us are fond of.”
Scroll through to look back at the icon’s greatest loves: