A guide to Hugh Hefner's many wives and girlfriends through the years

Playboy Magazine founder Hugh Hefner died Wednesday surrounded by friends and family at the Playboy Mansion. While building his lifestyle empire, Hefner also became quite the ladies man.

Hefner has been married three times and has dated a number of Playboy bunnies since 1949. While he has claimed to have slept with over 1,000 women in his 91 years of life, only some have been able to call themselves his girlfriend and even fewer his wife.

Keep reading to see the most prominent women who have been in Hefner’s life.

Hugh Hefner married his first wife Mildred Williams in 1949. They met at Northwestern University.

Williams admitted to cheating on him before their wedding when he was in the army.

"I had literally saved myself for my wife, but after we had sex she told me that she'd had an affair. That was the most devastating moment in my life," said Hefner in 2007 to the Daily Mail. 

The couple stayed together for a another decade, but divorced in 1959. The had two children together, Christie and David. Christie Hefner was the Playboy Enterprises Chairman and CEO for 20 years until she stepped down in 2008.

Hefner dated Barbara Lynn Klein from 1969 to 1976 and convinced her to change her name to Barbi Benton.

Benton appeared on the cover of Playboy in 1969, 1970, 1972, and 1985. After dating Hefner, she married real-estate developer George Gradow in 1979.

Shannon Tweed dated Hefner briefly after being named 1982 Playmate of the Year.

The "Falcon Crest" star dated Hefner until she started a relationship with "Kiss" singer Gene Simmons, who were married in 2011. They have two children together.

Carrie Leigh lived with and dated Hefner for five years in the '80s before leaving him.

Leigh filed three lawsuits against Hefner after they broke up, including one for publishing unauthorized photos of the model.

She described the Playboy Mansion as a cult to The Washington Post in 1999.

"When you live in an environment like that that's so different from how other people live, you start forgetting who you are and what you believe is right," said Leigh of living in the Playboy Mansion. "It's like the song 'Hotel California' — 'Mirrors on the ceiling, pink champagne on ice. We're all just prisoners here.' You know? 'You can check out any time you like, but you can never leave'? It took me a few years after I did leave to wipe it out of my head."

Kimberley Conrad became Hefner's second wife when she was 26 in 1989.

Conrad and Hefner had two children, Marston and Cooper. Though they were separated in 1998, Hefner waited until 2009 to file for divorce citing irreconcilable differences.  

"I would’ve been happy to divorce her when we separated, but she wanted to remain married for our boys," Hefner told People in 2009.

From the time Hefner and Conrad separated in 1998, he dated a multitude of Playmates, including actress Brande Roderick.

The "Baywatch" actress was Playmate of the Year in 2001. She married former NFL linebacker Glenn Cadrez in 2007 and they have one child together.

Hefner told The Daily Beast he dated several women at the same time along with Roderick for the next two years.

"Almost at the same time I met a pair of twins named Sandy and Mandy Bentley," Hefner told The Daily Beast of his relationships after his second wife. "For the next two years, my live-in girlfriends were Brande, Mandy, and Sandy—which reads like bad fiction, but was true."

Tina Marie Jordan was among one of the seven women Hefner dated in the early 2000s.

Hefner made Tina Marie Jordan the Playmate of the Month in March 2002.

When Hefner and Roderick broke up, he added a bigger rotation of girlfriends, including Izabella St. James.

"When the relationship with Brande broke up, I added more girls," said Hefner in 2011 to The Daily Beast. "At one point, it was up to seven. Izabella was one of those seven."

St. James moved into the Playboy Mansion in 2002 and lived there for two years.

Then there were live-in girlfriends Holly Madison, Bridget Marquardt, and Kendra Wilkinson.

The trio were featured on E!'s "The Girls Next Door," which debuted in 2005. The show ran for six seasons. 

Wilkinson is now married to Philadelphia Eagles' Hank Baskett and the two have a daughter and son. Madison is married to Pasquele Rotella and they have two children.

Afterwards, he dated 20-year-old twins Karissa and Kristina Shannon who appeared on the final season of "The Girls Next Door."

The twins moved out of the Playboy Mansion and into the Playmate House in 2010. The two claimed the move was because they were dating younger men. 

At the same time, he was dating Crystal Harris who eventually became his third wife.

Hefner became engaged to a 24-year-old Harris in December 2010. Though she broke off their engagement before their planned 2011 wedding, the two were eventually wed in December 2012.

Since Hefner's death, Harris deleted her Instagram and her Twitter account has been set to private. It has been reported she will "inherit nothing" of Hefner's fortune due to their pre-nup. 

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