Before Playboy mogul Hugh Hefner takes a trip to the
altar to marry on-again, off-again girlfriend Crystal Harris, take a
trip down memory lane with omg! as we look back at some of Hef's
gal pals from over the years.
Mildred Williams
It’s hard to imagine Hef with someone his own age, but long before he was a media mogul, Hef married fellow 23-year-old Mildred Williams in 1949. The couple went on to have two children – daughter Christie, now 60, and son David, now 57 – before divorcing in 1959. Christie would grow up to become chairwoman and CEO of Playboy Enterprises.
It’s hard to imagine Hef with someone his own age, but long before he was a media mogul, Hef married fellow 23-year-old Mildred Williams in 1949. The couple went on to have two children – daughter Christie, now 60, and son David, now 57 – before divorcing in 1959. Christie would grow up to become chairwoman and CEO of Playboy Enterprises.
Barbi Benton
Beauty Barbi Benton became Hefner’s main squeeze in the late ‘60s after meeting him while working as a model on his TV show “Playboy After Dark,” when Benton was just 18 and the magazine publisher was 42. Benton eventually released a few country music albums, starred in iconic TV series “Hee-Haw,” and appeared on the cover of Playboy a whopping four times, including in 1982, six years after she and Hef broke up.
Beauty Barbi Benton became Hefner’s main squeeze in the late ‘60s after meeting him while working as a model on his TV show “Playboy After Dark,” when Benton was just 18 and the magazine publisher was 42. Benton eventually released a few country music albums, starred in iconic TV series “Hee-Haw,” and appeared on the cover of Playboy a whopping four times, including in 1982, six years after she and Hef broke up.
Shannon Tweed
Before she became Kiss guitarist Gene Simmons’ better half, actress Shannon Tweed, who was bestowed with the honor of Playboy’s Playmate of the Year in 1982, was hoping to become Mrs. Hugh Hefner. "When Shannon says 'Why don't we get married?' and I say no, she punches me. I think having kids is a reason for getting married. I've had two," Hef told People in December 1982, after the couple had been dating for 14 months. "Shannon [27 at the time] is unusually mature and I'm not the average 56-year-old. A lot of the boy is left in me." Tweed moved on to Simmons the following year and married him 28 years later … in a wedding ceremony Hef attended!
Before she became Kiss guitarist Gene Simmons’ better half, actress Shannon Tweed, who was bestowed with the honor of Playboy’s Playmate of the Year in 1982, was hoping to become Mrs. Hugh Hefner. "When Shannon says 'Why don't we get married?' and I say no, she punches me. I think having kids is a reason for getting married. I've had two," Hef told People in December 1982, after the couple had been dating for 14 months. "Shannon [27 at the time] is unusually mature and I'm not the average 56-year-old. A lot of the boy is left in me." Tweed moved on to Simmons the following year and married him 28 years later … in a wedding ceremony Hef attended!
Carrie Leigh
Though Hugh Hefner has a knack for remaining friendly with many of his exes, 1983 Playboy cover girl Carrie Leigh wasn’t one of them. Leigh, who started dating Hef in 1983 – when she was 19 and he was 57 – moved into her new boyfriend's fabled mansion and sued Hefner for $5 million in palimony after the two broke up. “He promised to marry me, he promised to have a child with me, promised to support me," she said at a press conference. She later got married to someone else and dropped the suit.
Though Hugh Hefner has a knack for remaining friendly with many of his exes, 1983 Playboy cover girl Carrie Leigh wasn’t one of them. Leigh, who started dating Hef in 1983 – when she was 19 and he was 57 – moved into her new boyfriend's fabled mansion and sued Hefner for $5 million in palimony after the two broke up. “He promised to marry me, he promised to have a child with me, promised to support me," she said at a press conference. She later got married to someone else and dropped the suit.
Kimberly Conrad
After 30 years of living as a bachelor (and a busy one at that), Hef decided to make another trip down the aisle at age 63, this time to marry a 1988 Playmate of the Month, Kimberly Conrad, who was just 27 at the time. Conrad gave birth to Hef’s other two children, sons Maston and Cooper, now 22 and 21 respectively. Hef and his second wife split after nine years together, but Hef didn’t actually file for divorce until 2009, shortly after Cooper turned 18, when he asked a judge to reduce his spousal support from $40,000 to $20,000 a month. Throughout their separation, Conrad had lived with the couple’s sons in a house conveniently located next door to the Playboy mansion.
After 30 years of living as a bachelor (and a busy one at that), Hef decided to make another trip down the aisle at age 63, this time to marry a 1988 Playmate of the Month, Kimberly Conrad, who was just 27 at the time. Conrad gave birth to Hef’s other two children, sons Maston and Cooper, now 22 and 21 respectively. Hef and his second wife split after nine years together, but Hef didn’t actually file for divorce until 2009, shortly after Cooper turned 18, when he asked a judge to reduce his spousal support from $40,000 to $20,000 a month. Throughout their separation, Conrad had lived with the couple’s sons in a house conveniently located next door to the Playboy mansion.
Sandy and Mandy Bentley
After Hefner’s second marriage ended in 1998, he was “beat up emotionally and bruised,” he later told The Daily Beast, and sought comfort in numbers. Two of the women he started seeing were Illinois-born twin sisters Mandy and Sandy Bentley, who quickly became residents of the Playboy Mansion and were featured on the cover of the lad mag in May 2000. However, Sandy reportedly didn’t want to be tied down to one person either, and when Hefner found out she was seeing someone behind his back, he showed her the door
After Hefner’s second marriage ended in 1998, he was “beat up emotionally and bruised,” he later told The Daily Beast, and sought comfort in numbers. Two of the women he started seeing were Illinois-born twin sisters Mandy and Sandy Bentley, who quickly became residents of the Playboy Mansion and were featured on the cover of the lad mag in May 2000. However, Sandy reportedly didn’t want to be tied down to one person either, and when Hefner found out she was seeing someone behind his back, he showed her the door
Tina Jordan
Single mother and former loan officer Tina Jordan also moved into the Playboy Mansion when she met Hefner (46 years her senior) in 2001 and became Playmate of the Month in March 2002, when she was 29. The couple broke things off in 2004.
Single mother and former loan officer Tina Jordan also moved into the Playboy Mansion when she met Hefner (46 years her senior) in 2001 and became Playmate of the Month in March 2002, when she was 29. The couple broke things off in 2004.
Brande Roderick
If you blinked, you might have missed Brande Roderick in the sea of blond girlfriends Hef has had over the last decade. The now 38-year-old dated the icon around 2000-2001 and (what do you know?) became a Playboy Playmate in 2001. After she and Hef broke things off, Roderick began an acting career and eventually married former NFL linebacker Glenn Cadrez, with whom she has a 2-year-old son.
If you blinked, you might have missed Brande Roderick in the sea of blond girlfriends Hef has had over the last decade. The now 38-year-old dated the icon around 2000-2001 and (what do you know?) became a Playboy Playmate in 2001. After she and Hef broke things off, Roderick began an acting career and eventually married former NFL linebacker Glenn Cadrez, with whom she has a 2-year-old son.
Izabella St. James
Polish-born Izabella St. James met Hefner at a Los Angeles nightclub in 2000, while she was a law school student at Pepperdine University. After getting her degree, she didn’t follow in the typical lawyer’s footsteps – instead she moved into the Playboy Mansion! She later went on to write the book Bunny Tales: Behind Closed Doors at the Playboy Mansion about being a housemate, which didn’t exactly endear her to Hefner. “Quite simply, Izabella … was one of a number of girls that I dated and lived at the house in the early part of 2001,” Hef later told The Daily Beast. “Despite what she writes, she didn’t leave of her own volition. She left because she was asked to leave because she didn’t get along with some of the other girls. She was in conflict with some of the nicer girls like Holly [Madison] and Bridget [Marquardt], and I kind of cleaned house.”
Polish-born Izabella St. James met Hefner at a Los Angeles nightclub in 2000, while she was a law school student at Pepperdine University. After getting her degree, she didn’t follow in the typical lawyer’s footsteps – instead she moved into the Playboy Mansion! She later went on to write the book Bunny Tales: Behind Closed Doors at the Playboy Mansion about being a housemate, which didn’t exactly endear her to Hefner. “Quite simply, Izabella … was one of a number of girls that I dated and lived at the house in the early part of 2001,” Hef later told The Daily Beast. “Despite what she writes, she didn’t leave of her own volition. She left because she was asked to leave because she didn’t get along with some of the other girls. She was in conflict with some of the nicer girls like Holly [Madison] and Bridget [Marquardt], and I kind of cleaned house.”
Holly Madison, Bridget Marquardt, and Kendra Wilkinson
And when Hefner "cleaned house," he was left with these three ladies: Holly Madison, Bridget Marquardt, and Kendra Wilkinson. Each woman caught his eye at various times, but they came together in 2005 for a reality series about life at the famed abode called “The Girls Next Door.” For six seasons, they shared their lives behind the walls at the mansion, but Hefner's relationship with each woman started to unravel. First, Wilkinson fell in love with NFL player Hank Baskett, who she went on to marry; Madison, his No. 1 girlfriend, dumped Hefner when he told her he didn’t want to get married again or any have more children (she's currently pregnant); and Marquardt was the last to leave, in 2009, because she wanted to become her own person. Although the romances fizzled, Hef has remained on (mostly) friendly terms with the trio of women.
And when Hefner "cleaned house," he was left with these three ladies: Holly Madison, Bridget Marquardt, and Kendra Wilkinson. Each woman caught his eye at various times, but they came together in 2005 for a reality series about life at the famed abode called “The Girls Next Door.” For six seasons, they shared their lives behind the walls at the mansion, but Hefner's relationship with each woman started to unravel. First, Wilkinson fell in love with NFL player Hank Baskett, who she went on to marry; Madison, his No. 1 girlfriend, dumped Hefner when he told her he didn’t want to get married again or any have more children (she's currently pregnant); and Marquardt was the last to leave, in 2009, because she wanted to become her own person. Although the romances fizzled, Hef has remained on (mostly) friendly terms with the trio of women.
Crystal Harris In 2008, Hefner met Crystal Harris at his annual Halloween bash at the Playboy Mansion. Just months later she moved in along with the Shannon Twins and quickly slipped into the role of No. 1 girlfriend. While Madison couldn’t get Hefner to commit to marriage, Harris did. Hefner popped the question over Christmas in 2010 and she said yes. However, the road to the altar wasn’t smooth. Weeks before their June 2011 wedding, Harris called it off and left Hefner red faced as he had already put her on the cover of the June issue of Playboy with the headline: "Introducing America's Princess, Mrs. Crystal Hefner." Oops! Although he swore off marriage (again!), he reunited with Harris a year later and in early December 2012 they announced that they were once again engaged. The star-studded nuptials are set to take place at the mansion on New Year’s Eve – though, as we’ve learned, anything can happen.
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