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11 surprising facts you (probably) never knew about Hugh Hefner

5 facts you may not know about Playboy magazine founder Hugh Hefner
WATCH: Playboy magazine founder Hugh Hefner died at the age of 91. Here are five things about him you may not have known.

Without question, Playboy magazine founder Hugh Hefner is a dichotomous figure.

Hefner died Wednesday in his home in Los Angeles at the age of 91. Playboy Enterprises confirmed he died of natural causes.

With his passing comes the question: Who was Hefner, exactly? On one hand, he was a swinging playboy himself, often surrounded by women and seen as a lecherous sleaze, and on the other, he was a philanthropist, a vocal activist for LGBTQ rights, civil rights and a supporter of gay marriage.

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What many people don’t realize is that Playboy magazine is and was chock-full of top-notch journalism, and the common remark “I’m buying Playboy for the articles” (in other words, not the nudity) is what makes the joke. People did actually purchase the mag for its written content.

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Slowly, over decades, the image of “Hef” grew larger than life, and soon the Playboy Mansion, the infamous grotto and all of the Playboy “bunnies” cemented Hefner’s legacy and what he’ll most likely be remembered as.

Hefner lived a long, interesting life despite all of the perceived craziness. Here are some things about Hugh Hefner you most likely didn’t know.

Hefner bought the crypt next to Marilyn Monroe’s

Purchased at the Westwood Village Memorial Park Cemetery in 1992 for $75,000, his plan was to be interred next to her for eternity. It looks like that’s still the plan.

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Hefner helped reconstruct the Hollywood sign, twice

Hilariously, Hefner purchased the “Y” in “Hollywood” with $27,000 of his own money for the second restoration. The first reconstruction took place in 1978, largely due to his fundraising efforts.

An endangered rabbit is named after Hefner

Sylvilagus palustris hefneri, also known as the Lower Keys rabbit, bears the Playboy founder’s name in recognition of his financial support.

Hefner’s first wife, Mildred, cheated on him while he was at war

When she admitted it, Hefner famously called it “the most devastating moment of my life.” (Later, Mildred felt such guilt over her transgression, she allowed Hefner to sleep with other women. They divorced after 10 years of marriage.)

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Hugh Hefner

His first real job was as a copywriter at Esquire magazine

He quit in 1952 after his request for a $5 raise was rejected. Playboy magazine’s first issue was released in 1953, a mere one year later.

Hefner gave avant-garde writing a chance in Playboy

One example is Charles Beaumont’s The Crooked Man, which looked at a homosexual society of the future where heterosexual men were persecuted for their preferences. Despite being rejected by other publications, Hefner published it in Playboy, along with many other contentious pieces.

Former president George W. Bush and politician John Kerry are his distant relatives

And that’s not all! Not only is he ninth cousins with both Bush and Kerry, but Hefner also claimed to be an 11th-generation direct descendant of William Bradford, one of the “pilgrims” who came to America on the Mayflower.

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A stroke in 1985 changed Hefner’s trajectory

Despite the minor nature of his stroke, it made him re-examine his priorities. The legendary Playboy Mansion parties were significantly reduced, and he handed over the reins of the Playboy enterprise to his daughter, Christie, in 1988.

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Hefner admitted to experimenting with bisexuality

A notorious ladies’ man married three times, Hefner said he dabbled in bisexuality after his first marriage ended. It was the beginning of the ’60s at the time, when swinging and orgies were de rigueur.

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Hugh Hefner mourners conflicted on legacy Playboy founder leaves behind
Hugh Hefner mourners conflicted on legacy Playboy founder leaves behind

Hefner was an obsessive chronicler

He was notorious for keeping track of his life to a painstaking degree. As of 2011, Hefner had almost 2,400 volumes of scrapbooks in the attic of his mansion, filled with pictures of his various parties and gatherings.

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His overuse of Viagra may have contributed to his hearing loss

The erectile medication has been linked to sudden sensorineural hearing loss (SSHL), and Hefner reportedly “popped the pills like Skittles.” (Ed. Note: The author of this article interviewed Hefner in 2009, and can attest that he could barely hear. His assistant at the time had to relay all questions.) It didn’t bother Hefner much, however. One of his former lovers said, “He would rather have sex than have his hearing.”