Nothing about Hugh Hefner and his life was ordinary. Hugh lived his life to the fullest and even in death, he made sure he left people in awe by having his remains placed beside Marilyn Monroe. Hugh, who built a publishing and entertainment empire on the idea that people should enjoy sex and life to the fullest, was the distant cousin of the ex-president George W. Bush. Hugh was a ninth cousin of Bush (removed twice) and Senator John Kerry (once removed). Hugh Hefner has two Guinness World Records to his name, one for being the longest-serving editor-in-chief of a magazine, and the other for holding the world’s largest collection of personal scrapbooks.  Here are the 11 facts that showcase the extravagant lifestyle that Hugh lived.

1 Hugh and his brother Keith Hefner were raised by strict Methodist parents.

For the colorful life he lived, Hugh had a strict and conservative upbringing. Hugh and his brother grew up in the 1920s on a quiet Chicago street lit with gas lamps. His mother was a school teacher and his father was an accountant. His parents raised him with some strict rules that reflected their Puritan morals. They were not allowed to swear, drink, play cards, or listen to the radio on Sunday. There was absolutely no hugging or kissing in the family. Hugh was allowed to sit on the workbench and could draw or sculpt with the colored clay when he was felt restless. Hugh was good at drawing and sculpturing using colored clay and was often found so lost in clay figures that he wouldn’t hear his mother when she called him.  Hugh also seemed totally disengaged which made teachers wonder if he could hear them. For such lack of attentiveness, his mother had him examined by a child psychologist at the Illinois Institute for Juvenile Research.

Hugh, even though he never excelled in school, was an intelligent person with an I.Q. of 152. He was voted “most likely to succeed” in high school. He graduated in the top quarter of his class in high school. He was drafted into the army and served stateside from 1944 to 1946. He graduated from the University of Illinois at Urbana–Champaign with a Bachelor of Arts in Psychology and a double minor in Creative Writing and Art. He earned his degree in two and a half years in 1949. For his graduate paper at Northwestern University, Hugh chose the subject of the behavioral analysis of sex and related U. S. Laws. The paper was titled “Sex Behavior and the U.S. Law.”(source)

2 Hugh worked with Esquire as a copywriter before starting Playboy. When he was denied a raise of $5, he quit Esquire and later on started Playboy.

Hugh started working with Esquire magazine in 1951 as a promotional copywriter at a salary of $40 per week. In 1952, when Hugh asked for a $5 raise, he was denied which made him quit the job. After 11 months, in 1953, Hugh started Playboy magazine. For the initial investment, Hugh had to take a mortgage, a loan of $600 from a bank, and raise $8,000 from 45 investors which included $1,000 from his own mother.  Hugh asked his father if he would invest in the magazine or loan him some money. His father thought the magazine was not a good business investment and declined. As Hugh was leaving, his mother took him aside and gave him a check for $1,000, not because she believed in the venture but because she believed in Hugh.

From that $1,000, Hugh bought photographs of Marilyn Monroe for $500 from a Chicago calendar maker. These pictures of Marilyn, which were nudes, were featured in the first issue of Playboy in December 1953. The first issue, in December 1953, was undated, and only about 54,000 copies were printed as Hugh himself was unsure that it would be successful enough to warrant a second issue.(1,2)

3 Hugh was an animal lover. He provided financial support to the endangered marsh rabbit. The rabbit species was named after him in honor of his support. At the age of 11, he wrote a poem “Be Kind to Dumb Animals” for which he received an award from Illinois Humane Society.

Hugh loved dogs, and when he broke up with former Playmate Shannon Tweed, they had a slight custody battle over their dog. Tweed said the dog ended up having puppies which they shared. The Playboy Mansion is one of the few residential properties in the U.S. to have a zoo license. According to his wife, one of the first things Hugh did after buying the mansion was to add the animals and the zoo. And just to make it a great environment for them, he added hilly areas and ponds to the otherwise flat land. The mansion had a dedicated Mansion’s Animals Department and a range of exotic animals in the zoo.(source).

4 Hugh was a virgin until he got married and was heartbroken by his first wife’s cheating. This betrayal is considered the origin of his playboy lifestyle.

In 1949, Hugh married the Northwestern University student Mildred Williams. Hugh met her in the mid-40s^ at the college. Hugh was a virgin until he got married. The couple had vowed to save themselves for the marriage, however, only Hugh kept his vow. His wife confessed to having an affair while he was away in the army. Hugh described the betrayal as the most devastating moment of his life. While married, Mildred allowed Hugh to have sex with other women out of guilt for her own infidelity and in the hope that it would preserve their marriage. They divorced in 1959, but Hugh did not re-marry for 30 years.(source)

5 Hugh supposedly had sex with more than 1,000 women, and some estimate it to be 2,000. However, in spite of the general perception, he is not the man who slept with the most women.  Pro wrestler Ric Flair and Basketball player Wilt Chamberlain both left Hugh miles behind by claiming to have had sex with 10,000 and 20,000 women respectively.

While Hugh’s playfulness started even when he was married, he claimed to have never cheated. He had sex with more than 1,000 women, and some even estimate it to be 2,000 women. When Esquire magazine asked Hugh how many women he had slept with, he said, “How could I possibly know? Over a thousand, I’m sure.” He also added that “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.”

Hugh also experimented with homosexuality. According to him, he was only “experimenting,” “testing the boundaries,” and was “just knocking down walls.” His homosexual encounter, according to him, was limited to him receiving oral sex for money from a man in downtown Chicago. However, Leigh (Hugh’s girlfriend from the 1980s) claimed to have interrupted Hefner’s liaisons with men a couple of times.

Hugh’s promiscuity might have created health problems too. According to his ex-girlfriend, Karissa, Hugh has gone nearly deaf due to the Viagra he’s been using to enhance his sex life. Even when people would lean down to his good ear to say something, there was hardly a time when he understood what was being said. Upon being advised to stop taking Viagra, Hugh said he would rather have sex than have his hearing.(1, 2,3)

6 Hugh Hefner doesn’t own the Playboy Mansion. He had to pay an annual fee to cover rent and other expenses like food and parties. This included the room and board for Hefner’s many live-in girlfriends.

Even though Playboy Mansion and Hugh Hefner are perceived inseparable, and while a popular perception is that Hugh Hefner is the owner of Playboy Mansion, the reality is far from that. According to the paperwork, when Hugh filed in court for his divorce in 2009, he claimed the Playboy Mansion was owned by Playboy Enterprise, and that he paid rent to live there. In addition to the rent for the bedroom he used, Hugh also paid fees to cover the expenses for food, parties, room, and boarding of his girlfriends. According to a business insider, Hugh paid only $100 for his rent while Playboy Mansion was under the ownership of Playboy Enterprise.

In June 2016, Playboy Mansion was sold to Daren Metropoulos for $100 million with the condition that Hugh must be allowed to stay in the mansion as long as he desires while paying rent of $1 million a year.(1,2)

7 Hugh had bought a jet for partying. It was worth $5.5 million and was called “The Big Bunny.” It was modified from a 119-foot-long DC-9, equipped with a living room, disco, and sleeping quarters with a round bed covered in fur. It also had showers and even a powder room suitable for up to 16 people.

When Hugh was 43, after a trip to London in 1963, Hugh purchased a custom-made, 119-foot plane for a whopping $5.5 million. Hugh named the plane “The Big Bunny” and installed spotlights on the wing tips so that the iconic rabbit could be seen flying through the air at night. He had to get special permission from the federal government to paint the plane black. He wanted his plane to stand out as there were no black planes at that time.

The main compartment also had a fully-stocked bar and discotheque, as well as two film projectors and a video machine. The in-flight meals included grand dishes like lobster and roast beef. Elvis Presley borrowed the aircraft, and it was used to transport orphans to the US when the Vietnam War ended.(source)

8 Hugh protected his children from his playboy lifestyle. When his daughter visited the Playboy Mansion as a teenager, the mansion was cleaned up in an effort to keep her from knowing what was going on, and when the two sons were raised at the Playboy Mansion, nudity was banned.

Known for his extravagant lifestyle, Hugh made an active effort to protect his children from witnessing his usual lifestyle. Gloria Steinem remarked to Weymouth that she’d been told stories about Christie’s teenage visits to her father’s house: “When Christie would turn up, the mansion was cleaned up, the kinky stuff put away, and the Parcheesi board taken out. There was this apparent effort to keep Christie from knowing what was going on.”

Another attempt by Hugh to protect his kids was the banning of nudity in the Playboy Mansion when he became the father of two sons whom he raised at the mansion. He changed the “Playmates at Play” signs to “Children at Play,” and the grounds were littered with the toys.(source)

9 Hefner advocated for gay rights in the 1950s. He also published a story about straight men being persecuted in a world where homosexuality was the norm after Esquire rejected it. And when he received angry letters for it, he replied that “If it is wrong to persecute heterosexuals in a homosexual society, then the reverse is wrong too”.

The Playboy founder was also an advocate for gay rights. In 1955, Hefner decided to publish a science fiction story that was rejected by Esquire magazine. This story, “The Crooked Man” by Charles Beaumont, described a dystopian future where heterosexuals are persecuted in a society where homosexuality is the norm. After the publication of the story, Hugh received much hate mail to which he replied, “If it is wrong to persecute heterosexuals in a homosexual society, then the reverse is wrong too”.

In his interview with “The Advocate,” Hugh claimed to have campaigned against the nation’s laws against sodomy and highlighted the AIDS crisis in the magazine through informative articles. He also argued that same-sex marriage was “a fight for all of our rights.” According to Hugh, “No one should have to subjugate their religious freedom, and no one should have their personal freedoms infringed.”(source)

10 In sharp contradiction to his public persona, Hugh Hefner was a charitable person. He gave Hunter S. Thompson’s wife $25,000 after her husband died when she was frozen out of his bank accounts. He donated twice to restore the Hollywood sign in addition to providing the initial funding for the first rape kit.

In 1978, the Hollywood Chamber of Commerce came to the conclusion that the only way to preserve the iconic Hollywood sign would be to completely replace the letters. The cost of replacing the letters would be $250,000 at that time. Hugh helped restore the sign by holding a fundraising event at the Playboy Mansion where the letters were auctioned off.  Once again, in 2010, Hugh donated $900,000 to the trust of public land that was trying to buy the land surrounding the Hollywood sign so that a new development wouldn’t block the sight of the sign.

When Martha Goddard who was a survivor of sexual assault initiated a movement to create a comprehensive rape kit and lobbied hard to get it into circulation, she received initial funding for the first rape kit from Hugh Hefner’s Playboy Foundation. Hugh also established the Hugh M. Hefner Foundation  in 1964 to facilitate “individual rights in our democratic society.”

Other notable charities of Hugh’s includes his support to the “Children of the Night” – a nonprofit organization dedicated to rescuing America’s children from the ravages of prostitution, and also contributions to Brandeis University from which Hefner’s daughter Christie graduated. In 2006, Hefner also made a $1 million donation to the UCLA Film and Television Archive for public screenings of American cinema, establishing the Hugh M. Hefner Classic American Film Program, and in 2007, he made a $2 million-dollar donation to the USC School of Cinematic Arts.(1, 2)

11 Hugh Hefner has roses delivered to Marilyn Monroe’s grave every day and is buried next to her. They never met.

Even though it was Marilyn Monroe whose pictures helped Playboy to become massively successful, Hugh and Marilyn never met. However, Hugh didn’t forget Marilyn’s contribution to his success. He had roses delivered to Marilyn’s grave every day. Joe DiMaggio, one of Marilyn’s former husbands, vowed to deliver roses to the site every day after Marilyn passed. When Joe passed away, Hugh took on the responsibility as a sign of respect. Hugh also bought the crypt right next to Marilyn’s for the price of $75,000 at Westwood Memorial Park in Los Angeles. Hugh said to The Times in 2009, that “Spending eternity next to Marilyn is too sweet to pass up.”

A surprise in Hugh’s will was he did not include his wife in his will. In addition to the absence in Hugh’s will, the iron-clad prenuptial agreement that Hugh had for the marriage will result in his wife not getting a single penny from the wealth Hugh left behind.(1,2)