The wives and girlfriends of Playboy's founder Hugh Hefner

The wives and girlfriends of Playboy's founder Hugh Hefner

Over the past 100 years we've met many wives, lovers and girlfriends of the king of men's entertainment. His particular style? Blondes, beautiful, with pronounced curves and young. Up to 60 years younger than him! Here is a review of his love life that began in the way you would least expect.

  • Since 1949, he dated hundreds of his Playboy models and was married 3 times.
  • He had simultaneously up to 7 girlfriends and the myth says he slept with over 1000 women.
  • From those 1000, only a handful had the privilege of touching his heart and soul.

1) Hugh Hefner was the typical conservative Northwestern University student, who married his only girlfriend, Mildred Williams a couple of months after he met her and consumed his love in 1949.

Hugh and his first wife Mildred

Guess what? She cheated on him after he went to the Army and crushed his heart. He was still and honorable man and stayed together for another 10 years after filing for divorce in 1959. And then, the frenzy started.

Barbi and Hugh in the Playboy Club. Source: PL GOULD/IMAGES/GETTY

2) After 10 years of being single, he found the love of a model just two years older than his daughter Christie. From 1969 to 1976 he dated Barbi Benton. She insisted they should travel and managed to take Hef in tours around the world.

Became even close friends with Hef's daughter and they would borrow each other's clothing. 

3) Dated the 1982 Playmate of the Year, Shannon Tweed. She dumped Hef for Gene Simmons, the singer of Kiss.

Carrey on the cover of the magazine

4) Changed from models to actress and dated for 5 years Carrie Leigh. About the Playboy Mansion in Los Angeles she would say 'You can check out any time you like, but you can never leave'?

5) Married a 26-year-old model called Kimberley Conrad in 1989. They had two boys together: Marston and Cooper (current working to represent California’s 30th Senate District). 

Brande and Hugh together. Source: Getty

6) Baywatch it is. Hugh fell in love from Brande Roderick after her role in the famous movie. 

Hugh and his 7 girls. Source: Getty

7) "When the relationship with Brande broke up, I added more girls" said Hugh. He lived with up to seven women in his house. All blonde and gorgeous like the model Izabella St. James.

Girls next door poster. Source: Ebay

8) "Girls Next Door": Holly Madison, Bridget Marquardt, and Kendra Wilkinson. The famous bunnies were featured on E! Entertainment Television show for 6 seasons. 

Hefner with the twins. Source: Alamy

9) 20-year old twins Karissa and Kristina Shannon. 

10) Last Love: Crystal Hefner. His third wife, at the age of 24 years old. 

Bruno Wahrmann Lockhart

Digital Media Expert. Journalist. Former TV host. University of San Diego Alumni. 6′ 4″ but my mom still calls me 'tiny'+ info

Related Articles

More News

More News