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16 Facts About Hugh Hefner You Didn’t Know


On Wednesday, September 27th, Hugh Hefner (aged 91), passed away of natural causes at the Playboy Mansion. The announcement was made by the Playboy Mansion officials and his passing leaves behind a legacy in adult entertainment.

Despite how some might feel about the nature of his work, Hugh Hefner was a pioneer in a lot of different ways, including LGBTQ rights, Civil Rights, and protecting the First Amendment. Hugh believed that freedom of speech and thought was an important part of the American dream.

Here are 16 facts about Hugh Hefner you might not have known, that take a look back at his career, his life, and the empire of adult entertainment that he created.

1. Hugh Hefner Once Worked for Esquire Magazine. His work there included being a copywriter, and apparently, when Hugh was refused a $5.00 raise on his paycheck, he immediately quit the magazine to start his own venture.

2. Shortly after leaving Esquire, Hugh filed for a Mortgage which gave him $600, received over $8,000 from 45 different investors, including $1,000 from his own Mother, who although didn’t condone his plan, had faith in him to succeed in his business.

3. In the early 90s, Hugh bought a burial plot next to Marilyn Monroe in Westwood Village Memorial Park Cemetery where he is scheduled to be buried, following his memorial service.

4. During WWII, Hugh served as a writer for a military magazine.

5. His first issue of Playboy sold over 50,000 copies and featured a nude Marilyn Monroe on the front cover.

6. Hefner was an early advocate for LGBTQ rights back in the 1950s when they published “The Crooked Man” a story about a dystopian future where heterosexuality is persecuted in a homosexual dominant society. When criticized about the story, Hefner said, “If it was wrong to persecute heterosexuals in a homosexual society, then the reverse was wrong, too.”

7. Also a Civil Rights advocate, in a bold move in the 1960s, Hefner sent black author Alex Haley to interview what most call the “American Hitler” and leader of the American Nazi Party George Rockwell. Haley would also be asked to interview Malcolm X and Martin Luther King Jr to feature stories in Playboy.

8. Hugh Hefner once experimented with bisexuality. In the late 60s, discrimination started taking a backseat during the sexual revolution, and by the 1970s people were more open to acceptance, even if there were taboos still in existence.

9. In the late 70s Hefner helped organize a fundraiser that helped restore the Hollywood Sign. The sign was under a great deal of disrepair, and its restoration helped push Hollywood into a brighter future.

10. In 2010, Hefner donated a whopping $900,000 needed by a local conservation group to help protect an endangered species of rabbit, which is now named after him, the Sylvilagus Palustris Hefneri.

11. In his later years, Hefner reportedly used so much Viagra to treat erectile dysfunction, that a side effect of the drug caused him to lose his hearing.

12. In the mid-1980s, Hefner suffered a major stroke that left him temporarily paralyzed and unable to speak. He managed to make a miraculous full recovery and vowed to live a healthier lifestyle after this occurred.

13. Hefner was once arrested for publishing and promoting obscene literature, but was later released due to a deadlocked jury. It’s crazy to think how close Hugh Hefner was to being convicted of this when nowadays it can be found literally anywhere on the internet.

14. Among his many various partners over the years, Hugh kept company with 5 different women and was married to 3 other women. Mildred Williams from 1949 – 1959, Kimberly Conrad from 1989 – 2010, and finally Crystal Harris in 2012, who is now widowed from Hugh in 2017.

15. Hefner admitted to sleeping with upwards of 1,000 women in his lifetime. He claimed that during his marriages, he was faithful, but when he hasn’t married anymore, he made up for it.

h15 Twitter | @hughhefner

16. Hugh Hefner holds the Guinness world record for the longest-running editor-in-chief for a published magazine.


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