Hugh Hefner, the charismatic Playboy founder and publisher who passed away on Wednesday, had a complicated relationship with women. But one thing we can’t argue with is that the man and the magazine both played a seminal role in bringing about a sexual revolution. Personally, Hugh Hefner was one of the first celebrities to publicly support women’s reproductive rights, as well as LGBT equality and racial justice.

“Without the Playmates, I’d be the publisher of a literary magazine.” – Hugh Hefner

There have been a lot of lurid publications throughout history, of course, but Playboy was able to become a global brand and cultural icon by going beyond the typical conventions of a skin mag at the time. Or at least, just enough to turn readers on and leave them wanting more. People who are attracted to women came for the sexy photos, and stayed (in theory) for the smart editorial.

Playboy‘s literary legacy is strong, cemented by the magazine’s balls-to-the-walls ethos where no hot topic is off-limits. Over the years, Playboy has published fearless essays and journalism; eye-opening interviews with Malcom X, Ayn Rand and Steve Jobs; and unforgetable fiction by Gabriel García Márquez, Haruki Murakami and Margaret Atwood.

Related: The Tenth Zine Is a Flawless Response to #GayMediaSoWhite

In 1970, Hugh Hefner even went insofar as to thank the Playmates for making Playboy more than just a boring literary journal. At the end of the day, that hackneyed joke was kind of right all along: People did read Playboy for the articles. Check out some of the hottest pieces of fiction and non-fiction to have appeared in the pages of the iconic publication.

“The Crooked Man,” Charles Beaumont (1955)

Originally rejected by Esquire, this short story envisioned a world where homosexuality was the norm and heterosexual men where heavily persecuted. Playboy received an onslaught of letters about how awful this scenario was, to which Hugh Hefner personally responded: “If it was wrong to persecute heterosexuals in a homosexual society, then the reverse was wrong, too.”

“Death of a Deceiver,” Eric Konigsberg (1995)

Playboy was the first publication to chronicle the real-life story of Brandon Teena, the 21-year-old transgender man who was raped and murdered in Nebraska. His story inspired the Oscar-winning movie Boys Don’t Cry.

“Fahrenheit 451,” Ray Bradbury (1954)

The science-fiction novel – about a society where censorship runs amuck and controversial books are burned – was published as a novel the year before, but it lit up in the collective consciousness only after it was subsequently serialized in Playboy.

“The Visitor,” Roald Dahl (1965)

Little known fact: Roald Dahl was a freak. The beloved children’s book author would sometimes dabble in more-adult-oriented material. Like this short story about Uncle Oswald, “the greatest fornicator in the world.”

“Sex Is Politics,” Gore Vidal (1979)

Gore Vidal was a regular contributor to Playboy. In one of his most celebrated pieces, “Sex Is Politics,” Vidal made the argument that politicians use sexual issues to control society – throwing darts at the heteronormative patriarchy that ruled American politics at the time. And still continues to.

“The Bog Man” by Margaret Atwood (1991)

Playboy scored a few points with feminists when it published a story by Margaret Atwood, the author of the Handmaid’s Tale. Atwood’s parlay in the magazine resulted in a story about cheating, affairs, and a 2,000-year-old corpse.