Drugs, DUIs & Death: Hugh Hefner’s Most Shocking Secrets & Scandals Uncovered

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Sep. 28 2017, Updated 5:33 p.m. ET

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Hugh Hefner died on Sept. 27 and left behind a legacy of drugs, sex and more. Click through these slides to relive the 91-year-old’s biggest scandals as RadarOnline.com reveals the secrets he wanted to take to the grave with him.

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Hefner started Playboy in December 1953 while he was married to Millie Williams. The couple welcomed two children, Christie and David, before they divorced in 1959. Hefner later revealed that his wife had an affair while he was overseas in the army.

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He bought the Playboy Mansion in 1971, and it later became a raunchy party scene for celebrities including Leonardo DiCaprio, Colin Farrell and Owen Wilson.

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The Playboy mogul had a small stroke in 1985, just one year before he married Kimberley Conrad.

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Hefner and Conrad had two sons, Marston Glenn and Cooper Bradford, before they split in 1998. Marston was later arrested for DUI in 2015.

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He began dating a slew of women shortly after — with one of his girlfriends being Holly Madison. The blonde later revealed in her tell-all memoir that Hefner gave her Quaaludes to get her to sleep with him the first time they met, but his other girlfriend Kendra Wilkinson slammed her claims, and revealed that she first had sex with Hefner when she was just 18-years-old.

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Madison also claimed that Hefner offered her $3 million to stay with him, but she still packed her things and left the mansion. Hefner later told Radar: “Over the course of my life I’ve had more than my fair share of romantic relationships with wonderful women. Many moved on to live happy, healthy and productive lives and I’m pleased to say remain dear friends today. Sadly, there are a few who have chosen to rewrite history in an attempt to stay in the spotlight. I guess, as the old saying goes: You can’t win ’em all!”

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Hefner was dragged into Bill Cosby's sexual assault drama, as one of his accusers listed Hefner in her suit! Chloe Goins claimed that Hefner played a role in her alleged assault her at the Playboy Mansion in 2008, but The Cosby Show actor denied the claims and defended Hefner.

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“Bill has been a good friend for many years and the mere thought of these allegations is truly saddening,” Hefner later told The ENQUIRER. “I would never tolerate this kind of behavior, regardless of who was involved.”

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Radar later uncovered that Hefner was listed in top Hollywood madam Hedi Fleiss’ “little black book”.

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Hefner tied the knot for the third time with 26-year-old Crystal Harrisin 2012. They remained a couple until his death — although he was sick for a majority of their marriage.

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“Hef is deteriorating rapidly,” an insider told The National ENQUIRER in May of this year. “He’s also stopped eating, which is a sure sign the end is near. His doctors say it’s just a matter of time.”

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“He was never right after his brother died the day before Hef’s 90th birthday,” the insider added.

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His son Cooper confirmed his declining health in August, telling The Hollywood Reporter: “It’s tough to watch him struggle, but I’m just happy it’s physical and not mental.”

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Now, Hefner will be buried next to longtime muse Marilyn Monroe when he is finally laid to rest.

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