The many loves of Hugh Hefner… and the ‘devastating’ marriage betrayal that turned him into a Playboy
HUGH Hefner built his life and career around beautiful women and boasted of bedding a thousand of them throughout his life.
But his Playboy lifestyle was sparked by the “devastating” betrayal of his first wife, who admitted to an affair days before their wedding – after he had waited TWO years to lose his virginity with her.
Mildred ‘Millie’ Williams was Hugh’s childhood sweetheart and Hugh was determined to “save himself” for her through his stint in the army, while she attended the University of Illinois.
But, after “two years of foreplay”, Hugh – who died yesterday at the age of 91 – was heartbroken to discover she had slept with someone else.
He said: “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. My wife was more sexually experienced than I was. After that, I always felt in a sense that the other guy was in bed with us, too.”
Despite the revelation, the pair tied the knot in 1949, and had two children – daughter Christie Hefner, born in 1952, and son David, born three years later.
But the betrayal cast a shadow over the marriage and, wracked with guilt, Millie gave her husband permission to sleep with other women during their marriage.
Millie was also instrumental in the setting up of Playboy which launched in 1953 with Marilyn Monroe as its first centrefold.
Hugh had wanted to call it Stag Party, but was threatened with legal action from rival mag Stag, so Millie, Hugh and pal Eldon Sellers came up with the name Playboy.
After ten years, in 1959, the marriage came to an end and the new lavish lifestyle that became synonymous with Hef began.
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He bought the original Playboy Mansion, in Chicago, reinvented himself as a man about town and surrounded himself with young beautiful models.
He also showcased his party lifestyle in the TV shows Playboy's Penthouse (1959–1960) and Playboy After Dark (1969–1970).
In 1971, Hef bought his second Playboy mansion - a 22-room Gothic-style pile in Los Angeles – for £800,000 and his parties became legendary throughout the 1970s.
Among his lovers at the time were the Playboy models Donna Michelle, Marilyn Cole, Lillian Müller, Shannon Tweed, Barbi Benton, Karen Christy, Sondra Theodore and he claimed to have slept with “maybe eleven out of twelve months' worth of Playmates" during his single years.
Sometimes his love life came back to bite him – as it did in 1988 when Carrie Leigh, his lover of six years, filed a £4 million palimony suit against him.
Carrie, who had moved into the famous Playboy mansion when she was 19 and Hugh was 57, said: “He promised to marry me, he promised to have a child with me, promised to support me.”
But Hugh batted off the charge, claiming: “I’m the silliest possible target for a palimony suit, because I’m the most confirmed bachelor of the 20th century.”
But he didn’t stay single for long.
After a minor stroke in 1985, at the age of 59, Hef decided to tone down his partying and wild lifestyle and in 1989, he wed Playmate of the Year Kimberley Conrad, who was 26 years his junior.
The couple has two sons - Marston Glenn, born 1990, and Cooper Bradford, born 1991, before separating in 1998.
While Hugh continued to live with multiple girlfriends in the now notorious Playboy Mansion, Kimberley moved into the house next door and the couple stayed married for 11 years, only divorcing when Cooper turned 18.
In 2004, the Playboy legend moved “number one girlfriend” Holly Madison into the house, along with other lovers Kendra Wilkinson and Bridget Marquardt and a year later the trio began starring in their own TV show, The Girls Next Door.
Holly split with Hugh five years later, and all three moved out, with both Holly and Kendra going on to star in their own spin off series.
Hugh moved buxom twins Kristina and Karissa in to the LA mansion, along with Crystal Harris – who was to become his third and final wife.
The Playboy mogul got engaged to Crystal – who was 60 YEARS younger – on Christmas Eve, 2010.
Six months later she dumped him, just five days before their planned wedding and after the July issue of Playboy – featuring Harris on the cover with the headline “Introducing America's Princess, Mrs. Crystal Hefner” – had hit the shelves.
Playboy issued a sticker reading “Runaway Bride” to cover the front page.
The pair did kiss and make-up, however, and on New Year’s Eve, 2012, they wed at the Playboy Mansion in a private ceremony – he was 86 and she was 26.
Hefner – who was survived by Crystal and his four children – is said to have left nothing in his will to his third wife.
