Hugh Hefner's Life in Pictures

There were few people over the past six decades who had as much of an impact on the world of sexuality as Hugh Hefner. He's had so much of an impact that he's earned one-name status: Hef. Hef's life was been one heck of a thrill ride, one filled with twists and turns in both business and his personal life. His life was so intriguing and spectacular that on April 7, 2017 — two days before his 91st birthday — Amazon aired a 10-episode documentary series "American Playboy: The Hugh Hefner Story." A few months later, on Sept 27, 2017, Hef passed away. Keep reading to check out the highs and lows of the publishing mogul's life…

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There's no debate about what put Hugh Hefner on the map. In 1953, at the age of 27, Hef published the first issue of Playboy with Marilyn Monroe on the cover. No one knew that it would be a turning point in society. Just a few years earlier, Hef was writing copy for Esquire magazine. Legend has it that he left that job after they refused to give him a $5 raise. He then decided to raise capital (he even got money from his mom) to start Playboy. Needless to say, it worked.

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In 1963, Hugh Hefner was arrested on obscenity charges after publishing a nude pictorial of actress Jayne Mansfield. Jayne was on Hef's side, saying, "Beauty cannot be obscene." The case went on for several months. Charges were eventually dropped when the case ended in a mistrial. Still, the publicity from the case only earned Playboy and the mogul more notoriety.

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While Hugh Hefner lived a life of glitz and glamour filled with sultry nights and plenty of skin, his family life suffered. Through the 1950s, he worked tirelessly to launch Playboy. Because of all of this, he admits that his family wasn't exactly his top priority, despite the fact that he had two young kids at the time, Christie and David. He told People in 2016 that he was an "absent dad." Still, fences seemed to be mended over time: Christie became president of Playboy in 1982 and its CEO in 1988, a position she held for 21 years.

In 1959, Hugh Hefner honed his inner Johnny Carson and became the host of "Playboy's Penthouse," a talk show that saw him chatting with celebrities while Playboy bunnies played around in the background. The show lasted two years. Hef created a similar show called "Playboy After Dark" in 1969.

Love has been a tricky thing for Hugh Hefner. In 1949 while living in Chicago, Hef married Mildred Williams. After 10 years, they were divorced. According to a 2006 episode of an "E! True Hollywood Story," Millie, as she was known, had cheated on Hef while he was away serving in the U.S. Army, admitted her affair and then let him be with other women during their marriage because of her guilt.

It was the home that changed everything for Hugh Hefner. In 1971, he purchased a property in Los Angeles' Holmby Hills neighborhood — a home that became better known as the Playboy Mansion. Almost immediately, Hef began throwing lavish parties at the residence and the "grotto" within the pool area became legendary. Invitations to his parties were one of the most coveted items in a town that knows all about parties, as they included celebrities and beautiful women. Fast-forward 45 years to a day no one ever expected would come: On Aug. 16, 2016, it was announced in a press release that the famous Playboy Mansion had been sold to Hef's neighbor for $100 million, which at the time was the most expensive home ever sold in Los Angeles County. The one caveat of the sale: Hef gets to live in the mansion until his death for $1 million a year.

It should come as no surprise that Hugh Hefner likes women. He's also not shy about how many women he's been with. While speaking to Esquire in 2013, he was asked how many women he's slept with, to which he replied, "Over a thousand, I'm sure. How could I possibly know?" He added, "There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn't married. You have to keep your hand in."

Hugh Hefner's health began to raise concerns in 1985 after he had a minor stroke. At the time, a book called "The Killing of the Unicorn" had been published — it was about the murder of a former Playmate and the magazine's financial decline. Many cited this book as the cause of Hef's medical episode. Afterward, he told the Chicago Tribune, "I suspect this will change the nature and focus of my life. 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."

Many only know Hugh Hefner as the man who brought Playboy to life and don't realize he's actually quite charitable too. Although he's a Chicagoan by birth, Los Angeles captured his heart. He helped restore the iconic "Hollywood" sign twice! In 1978, he dropped $27,000 to purchase the "Y" in the sign in an effort to restore it to its original glory. In 2010, he paid $900,000 to help a group that was trying to stop development around the sign. He also once gave the University of Southern California $2.1 million for its cinematic arts program. He gives money to animal rights organizations. Through his charity, the Hugh M. Hefner Foundation, he advocates for defending civil rights and civil liberties with a special emphasis on First Amendment rights and rational sex and drug policies.

Hugh Hefner found love again in the '80s after meeting Kimberly Conrad, a woman 37 years his junior. Kimberly was featured as Playboy's Playmate of the Month in January 1988 and was named Playmate of the Year in 1989, which was also the same year that she and Hef tied the knot (his second marriage). They went on to have two children, Marston and Cooper. After nine years, though, their marriage essentially collapsed and the two separated but remained married for the kids. Their separation lasted 11 years. They officially divorced in 2010.

Hugh Hefner reintroduced himself to younger generation in 2005 when he starred on the E! reality show "The Girls Next Door," a series that chronicled his life with his three — yes, three — girlfriends: Holly Madison, Bridget Marquardt and Kendra Wilkinson (all of whom were significantly younger than him). Camera crews detailed every bit of his life and the relationships he had with the three blondes, all of whom lived in the Playboy Mansion at the time. His relationship with the three Playmates ended in 2008 and 2009, but he continued filming the show for another season in 2010 with cameras showcasing his relationships with then-19-year-old twins Kristina and Karissa Shannon and then-23-year-old Crystal Harris. Crystal was called his "No. 1 girlfriend."

Crystal Harris was the one that got away… only to come back to Hugh Hefner. Hef and Crystal became engaged in late 2010. They set a wedding date for June 19, 2011. But five days before they were supposed to walk down the aisle, Crystal called off the wedding and ran away. At the time, she was on the cover of Playboy, which was intended to publicize the wedding. Soon after she fled, stickers were placed on the cover that read "Runaway Bride." As this unfolded, and he was suddenly single, Hef told The Hollywood Reporter, "The truth of the matter is, I should be single. I'm better served that way. Maybe I don't pick the right women. Or maybe I'm just too complicated." Shortly after all that, Hef and Crystal reconciled and finally married on Dec. 31, 2012. He was 86; she was 26. They reportedly have an "ironclad" prenuptial agreement.

In 2015, Hugh Hefner's former girlfriend Holly Madison wrote a book about her time in the Playboy Mansion and it was none too flattering to her ex. In "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," Holly claimed Hef offered her drugs the first time they met. "'Would you like a Quaalude?' Hef asked, leaning toward me with a bunch of large horse pills in his hands, held together by a crumpled tissue," she wrote. "Hef did not miss a beat: 'Okay, that's good,' he said, nonchalantly. 'Usually, I don't approve of drugs, but you know, in the '70s they used to call these pills thigh-openers,'" she claimed he told her. She said he was manipulative, pitted women against each other and even tried to buy her off in his will. "It was there, in black and white," she wrote. "The will stated that $3,000,000 would be bestowed to Holly Madison at the time of his death (provided I still lived in the Mansion)." Hef denied nearly everything Holly wrote, equating her story to a book of fiction.

Did 2008 come back to haunt Hugh Hefner in 2016? Chloe Goins sued Hef and Bill Cosby that year for sexual battery, gender violence and other alleged crimes stemming from a 2008 incident she said occurred at the Playboy Mansion. In the lawsuit, she claimed that Hef was known for inviting young, impressionable women to his house and plying them with alcohol and drugs to loosen their inhibitions. Hef, she alleged, introduced her to Bill while knowing that he "had a history of severe and serial sexual battery and or possibly rape of women [and] was negligent at the very least." The lawsuit stated that Hef "knew or should have known such actions would lead to harm." A few years prior, a woman sued the comedian alleging that he'd molested her at the Playboy Mansion when she was 15 years old. "Bill Cosby has been a good friend for many years and the mere thought of these allegations is truly saddening," Hugh said in a statement at the time. "I would never tolerate this kind of behavior, regardless of who was involved."

The headlines read "Hugh Hefner is gravely ill" and "Hugh Hefner is down to 90 pounds." That was in 2016. The funny thing is, that was all news to Hef himself. But it wasn't the first time the media had printed stories claiming that he was in decline. Hef, still sharp as a tack, took to Twitter (yes, he tweets) to poke fun at the reports. "I wish the tabloids had informed me a little earlier in the week that I'm sick," he wrote. "I might have canceled my weekend plans."

On Sept. 27, 2017, Hugh Hefner passed away. In a statement, his son Cooper Hefner said, "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."