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Hugh Hefner Dead: ‘Playboy’ Founder Dies at 91

Hugh Hefner, the iconic founder of Playboy, died on Wednesday, September 27. The businessman was 91.

“My father lived an exceptional and impactful life as a media and cultural pioneer and a leading voice behind some of the most significant social and cultural movements of our time in advocating free speech, civil rights and sexual freedom. He defined a lifestyle and ethos that lie at the heart of the Playboy brand, one of the most recognizable and enduring in history. He will be greatly missed by many, including his wife Crystal, my sister Christie and my brothers David and Marston, and all of us at Playboy Enterprises,” his son Cooper Hefner said in a statement.

Hugh Hefner
Hugh Hefner on November 17, 2005 in Los Angeles, California. Dan Tuffs/Getty Images

Born Hugh Marston Hefner on April 9, 1926, in Chicago, Illinois, Hefner was the oldest of two boys born to Grace and Glenn Hefner. He graduated high school in 1944 and joined the Army. He later earned a Bachelor’s degree from the University of Illinois at Urbana-Champaign. 

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In 1949, he married his first wife, Millie Williams. After they welcomed daughter Christie and son David in the early 1950s, they divorced in 1959. In 1985, he suffered a stroke right before his 59th birthday and reevaluated his behavior. 

“I suspect this will change the nature and focus of my life,” the entrepreneur told the Chicago Tribune at the time. “To have that experience and come back from that is something of a miracle and blessing. When you come that close to the edge and look over, the dramatic nature of what occurred gave me permission in a single day to drop the luggage of a lifetime.” 

In 1989, he married Playmate of the Year Kimberley Conrad, and together they had sons Marston and Cooper. The couple separated in 1998 and she moved into a home adjacent to the Playboy Mansion. They didn’t officially divorce until 11 years later. He went on to marry Crystal Harris. The couple had originally planned to wed in June 2011, but just five days before their nuptials, Crystal made the controversial decision to call things off. They later reunited and married on New Year’s Eve 2012. 

“I tried marriage twice before but there’s no comparison,” Hugh told Us Weekly in 2014 of his marriage to Crystal. “This is the real deal. And to find true love at this age? It’s remarkable.”

Holly Madison, Hugh Hefner, Bridget Marquardt Kendra Wilkinson
Holly Madison, Hugh Hefner, Bridget Marquardt and Kendra Wilkinson on October 7, 2006. Jamie McCarthy/

The first issue of Playboy, which featured actress Marilyn Monroe on the cover, was produced on a kitchen table in Hugh’s South Side Chicago apartment. 

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“The first few days, weeks told me that there was an audience out there and that was all I needed,” Hef told Us at the magazine’s 60th anniversary party in 2014. “It was the best surprise. I had no idea and I was so fortunate. I had no idea what lay ahead — it’s unreal what it’s become.”

Playboy Enterprises went public in 1971 and at the time there were 23 Playboy clubs, resorts, hotels, and casinos worldwide. Playboy Mansion West was acquired in 1971, and several years later Hugh made it his personal residence. 

The mansion has become exclusively linked to Hef and was featured on the reality series The Girls Next Door, which ran for six seasons in 2005 and starred the Playboy founder and his many girlfriends, including Kendra Wilkinson, Holly Madison, and Bridget Marquardt.

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Hef also loved to celebrate his birthday, starting the annual tradition of screening his favorite film, Casablanca, at the Playboy Mansion. “Casablanca is my all time favorite film and we watch that movie and then gather in the dining room, which we have transformed into Rick’s Café Américain and we have Champagne and caviar by candlelight,” Hugh told Us in 2011 of the tradition. “It’s a very romantic evening. Everyone dresses up in the style of the 1940s, similar to the movie.”

Hef has been applauded for his humanitarian and charity work through the years. He has worked to restore the iconic Hollywood sign, referring to it as “Hollywood’s Eiffel Tower,” which earned him a star on the Hollywood Walk of Fame. 

A longtime lover of film, Hugh has donated millions of dollars to the UCLA Film & Television Archive and the USC School of Cinematic Arts in his lifetime.

He is survived by his wife, Crystal, and his four children. 

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