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AFP/Getty Images

The year was 1955, and science fiction author Charles Beaumont had, by most accounts, crossed the line with his latest short story.

“The Crooked Man” depicted a dystopian future where homosexuality was the norm, heterosexuality was outlawed and angry anti-straight mobs marched through the street chanting “make our city clean again!” Even the relatively progressive Esquire magazine had rejected the piece because it was too controversial.

But Beaumont found a fan in a young Hugh Hefner, who agreed to run it in his Playboy magazine, then less than two years old.

Outraged letters poured in to Playboy. Even readers of the pioneering nude publication found Beaumont’s tale of straight people dressing in drag and sneaking into dark barrooms to find partners too offensive for their tastes.

Hefner responded to the backlash in a defiant note. “If it was wrong to persecute heterosexuals in a homosexual society,” he <a href="https://www.advocate.com/news/daily-news/2009/08/28/hugh-hefner-gay-rights-pioneer" target="_blank">wrote</a>, “then the reverse was wrong, too.”

The move would serve to represent an early example of Hefner’s lifelong commitment to gay rights, and civil rights in general. Hefner, who died Wednesday at 91, prided himself as an advocate for the LGBT community, taking public stands on high-profile issues such as sodomy laws, same-sex marriage and transgender rights well into his later years.

The anecdote about “The Crooked Man” was little known until 2009 when it was highlighted in “<a href="http://www.imdb.com/title/tt1503776/" target="_blank">Hugh Hefner: Playboy, Activist and Rebel</a>,” a documentary on Hefner’s civil rights advocacy. The film expounds on Hefner’s efforts to promote black writers and artists, expand reproductive rights and resist racial segregation. Some <a href="http://content.time.com/time/arts/article/0,8599,2007993,00.html" target="_blank">criticized</a> the documentary for glossing over the more controversial aspects of his legacy, namely drug abuse and sexism, while others <a href="https://www.slantmagazine.com/film/review/hugh-hefner-playboy-activist-and-rebel" target="_blank">dismissed</a> it as a shrewd attempt to remake his image.

Indeed, Hefner’s life was full of contradictions that are sure to be debated exhaustively in the days and weeks following his death. He portrayed himself and his magazine as defenders of women’s rights, but his critics have called him anything but, pointing to his rotating cast of girlfriends, multiple divorces and general objectification of women in the pages of Playboy (“They <em>are</em> objects,” he once told <a href="https://www.vanityfair.com/hollywood/2017/09/hugh-hefner-dies-dead-playboy" target="_blank">Vanity Fair</a>).

A widely publicized memoir by one of his former girlfriends, Holly Madison, described a life of manipulation and constant fighting at the Playboy Mansion. Hefner was also <a href="http://www.hollywoodreporter.com/thr-esq/hugh-hefner-demands-dismissal-lawsuit-902277" target="_blank">accused</a> last year of paving the way for Bill Cosby to drug and sexually assault a woman at the famed estate in 2008. Hefner denied the allegation.

Elyse Samuels

Hefner’s contradictions weren’t lost on <a href="https://books.google.com/books?id=JGMEAAAAMBAJ&amp;pg=PA42&amp;lpg=PA42&amp;dq=playboy+sodomy+laws&amp;source=bl&amp;ots=O_jP2X94tj&amp;sig=_IrOREDHswRXNysr08ozYkvlKE0&amp;hl=en&amp;sa=X&amp;ved=0ahUKEwiTi8ujocfWAhUK6CYKHZqxDx4Q6AEIRjAH#v=onepage&amp;q=playboy%20sodomy%20laws&amp;f=false" target="_blank">the Advocate</a>, a gay magazine that published a wide-ranging interview with him in 1994. Hefner told writer Jeff Yarbrough their magazines had a lot in common in the sense that they were both “anti-discrimination.” Yarbrough was caught off guard.

“What surprises me about that statement is that Playboy and you, of course, are both known as representations of male heterosexuality and, to some degree, the objectification of heterosexual women,” Yarbrough told him. “I’m surprised you recognize the issue of oppression concerning gays and lesbians so clearly at a time when most Americans still don’t.”

Asked if he considered himself a gay rights activist, Hefner responded that he had been a “human rights activist” from the magazine’s inception. He said he had campaigned against the nation’s sodomy laws, which criminalized certain sexual acts. “If the pursuit of happiness has any meaning at all as it is written in the Constitution, the government’s intruding into one’s bedroom, into personal sexual behaviors, is as unconstitutional as anything can be,” Hefner said.

The interview also touched on the AIDS crisis, which “profoundly changed Hefner’s life” in the early 1980s, Yarbrough wrote. Hefner fixated on the disease soon after it was identified, he wrote, and used Playboy to keep a spotlight on the epidemic “with articles that examine everything from the disease’s origins to safer sex practices.”

Hefner told the Advocate: “The only thing ‘wrong’ with AIDS is the way our government responded to it. They are culpable on many, many levels. … I have chosen every aspect of human sexuality — and the discrimination that goes along with some of those aspects — as my major concern. Homosexuality and, later, the homophobia that surrounds the AIDS crisis are part of a much bigger picture for me.”

Long before Caitlyn Jenner became a household name, Hefner took something of a symbolic stand on transgender rights. In the 1980s, model and actress Caroline “Tula” Cossey was outed as a transgender woman by the tabloid News of the World and subjected to intrusive headlines. Playboy helped her bounce back from the ordeal by publishing a photo series with Cossey, making her the magazine’s first openly transgender model.

When the magazine reran the spread in 2015, Cossey thanked Hefner by name, saying the exposure helped her show that transgender women can be sexy. “I wanted to fight for the right of recognition,” she told <a href="http://www.playboy.com/articles/tula-first-transgender-in-playboy-1991" target="_blank">Playboy</a>. “That was my goal, and Playboy was a great platform for that.”

Hefner came out forcefully in support of same-sex marriage just as a group of marriage equality lawsuits were weaving through the federal court system. In a commentary in the September 2012 issue of Playboy, Hefner, then 86, <a href="http://www.politico.com/story/2012/08/hefner-gay-rights-under-assault-079930" target="_blank">argued</a> that same-sex marriage was “a fight for all of our rights.”

“Without it, we will turn back the sexual revolution and return to an earlier, puritanical time,” he wrote. He railed against people trying to “criminalize your entire sex life,” using language that echoed his remarks to the Advocate decades earlier.

“No one should have to subjugate their religious freedom, and no one should have their personal freedoms infringed,” Hefner wrote. “This is America and we must protect the rights of all Americans.”

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<a href="https://www.washingtonpost.com/news/morning-mix/wp/2017/09/28/judge-strikes-down-kentucky-antiabortion-law-requiring-ultrasound/" target="_blank">Judge strikes down Kentucky antiabortion law requiring ultrasound</a>

<a href="https://www.washingtonpost.com/news/morning-mix/wp/2017/09/28/missouri-prosecutors-brutal-murder-of-transgender-teen-is-not-a-hate-crime/" target="_blank">Missouri prosecutors: Brutal murder of transgender teen is not a hate crime</a>

<a href="https://www.washingtonpost.com/news/morning-mix/wp/2017/09/28/megyn-kelly-is-striking-out-with-her-celebrity-guests/" target="_blank">Megyn Kelly is striking out with her celebrity guests</a>

<a href="https://www.washingtonpost.com/news/morning-mix/wp/2017/09/28/a-police-officer-posted-a-dont-drink-and-drive-video-then-he-was-in-a-deadly-crash-and-booked-on-suspicion-of-dui/" target="_blank">An police officer posted a ‘don’t drink and drive’ video. Then he was involved in a deadly crash.</a>

Northeastern University, BA in journalism

Derek Hawkins is a reporter and editor on The Washington Post's National desk focusing on visually-driven stories. 

Derek Hawkins

The Washington Post

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