Hugh Hefner’s Wives & Girlfriends — Pics

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September 28, 2017 12:54AM EDT

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Holly Madison dated Hugh Hefner for seven years and was at one point considered his ‘No. 1’ girl. Holly was one of the stars on ‘The Girls Next Door’ and has written two scandalous memoirs about her time with Hef. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Holly Madison was hef’s “No. 1” for seven years. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Kendra Wilkinson was another one of Hef’s co-stars on ‘The Girls Next Door.’ She moved into the Playboy Mansion when she was just 18! Kendra ended up marrying her husband, NFL player Hank Baskett, at the mansion in 2009. She has since starred in a spinoff series titled ‘Kendra,’ written a tell-all and competed on ‘Dancing with the Stars.’ (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Kendra Wilkinson was one of Hugh’s co-stars on ‘The Girls Nextdoor.’ (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Kristina Shannon and Karissa Shannon, the Shannon Twins, both dated Hugh at the same time and lived in the Playboy Mansion! (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — The Shannon Twins were both Hugh’s girlfriend! (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Crystal Harris is a former Playmate of the Month and was engaged to Hef twice before they finally got married in 2012. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Crystal Harris was Hef’s wife at the time of his death on Sept. 27, 2017. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Bridget Marquardt was one of Hugh’s girlfriends from 2002 to 2008, and one of the Playboy models who starred on ‘The Girls Next Door.’ (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Izabella St. James was a Polish Playmate and the very first of Hef’s former lovers to write a tell-all about their romance. She dated him from 2002 to 2004. Izabella is known for attacking Holly in the media. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Brande Roderick, a former ‘Baywatch’ actress, dated Hugh from 2000 to 20001. Brande has since married former NFL player Glenn Cadrez and started a family. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Brande Roderick was one of Hugh’s main loves. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Holly Madison, Bridget Marquardt and Kendra Wilkinson were Hugh’s ‘The Girls Nextdoor’ co-stars and girlfriends. (REX/Shutterstock)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Kimberley Conrad Hefner was Hugh’s second wife. They were married from 1989-2010. (Courtesy of Playboy)

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Hugh Hefner & The Women Who Loved Him

Hugh Hefner & The Women Who Loved Him — Crystal Harris was Hugh’s third wife. (REX/Shutterstock)

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