
Hugh Hefner was best known for creating ‘Playboy’ magazine, but he was also known for his playboy lifestyle. When Hugh died at the age of 91 in 2017, he had been married three times, but there were plenty of other women in his life throughout his years. While the magazine creator had been with hundreds of women, there were a handful that also got to be his official ‘girlfriends.’ Hugh sometimes dated many women at one time, as well.
During ‘The Girls Next Door’ years, Hugh dated Holly Madison, Bridget Marquardt, and Kendra Wilkinson all at the same time, and all three lived in the Playboy mansion with him. Hugh was married to Crystal Hefner at the time of his death, and her new memoir, ‘Only Say Good Things: Surviving Playboy and Finding Myself’ hit shelves in January of 2024.
Click through to see photos of Hugh’s wives and girlfriends over the years in our official gallery.
Hugh & ‘The Girls Next Door’

Hugh Hefner & Sondra Theodore

Mildred ‘Millie’ Williams

Hugh Hefner & Barbi Benton

Shannon Tweed

Hugh Hefner & Carrie Leigh

Hugh Hefner & Kimberley Conrad

Hugh Hefner With Mandy & Sandy Bentley

Hugh Hefner & Brande Roderick

Izabella St. James

Hugh Hefner & Holly Madison

Hugh Hefner & Bridget Marquardt

Hugh Hefner & Kendra Wilkinson

Hugh Hefner With Kristina & Karissa Shannon

Hugh Hefner & Crystal Harris
