Playboy founder Hugh Hefner died yesterday at 91. No matter your personal feelings about the man or his work, Hefner printed “more serious journalism and fiction than just about any other magazine publisher,” as CJR’s Pete Vernon notes. Yes, the magazine invented the centerfold, but it also earned a literary legacy in its 60-plus years.

Playboy has published extensive interviews, compelling profiles, deep-dive investigations, short stories, and essays, in between its NSFW photo spreads. The Playboy archives are a trove of journalistic might, and fascinating fodder for anyone interested in writing, culture, politics, or any combination of those. Below, we’ve gathered just a few examples of some of the great journalism to grace the pages of Hefner’s Playboy.

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Death of a Deceiver, Eric Konigsberg, January 1995

 Konigsberg’s piece on the violent murder of Brandon Teena, a transgender man from Nebraska, was the first of its kind (though its language would be considered tone-deaf by today’s standards). Teena’s life and death became the subject of the Academy Award-winning film, Boys Don’t Cry, starring Hilary Swank.

Teena Renae Brandon’s mystery was over the moment her body was discovered, facedown on a bed in a farmhouse in Humboldt, Nebraska. It was early in the morning on December 31, 1993, and lying dead with Teena were two others. Each of the three had been shot twice, execution style, with a .38 revolver. “Through and through” is how the coroner would classify their wounds, meaning the bullets had entered the victims’ heads from side and exited the other. In addition, Teena had been stabbed in the liver and her skull had been crushed. She was 21.”

Word of the triple murder raced through Humboldt, a town of 1330. At a bar called Big Mike’s, townspeople gathered around a police scanner awaiting identification of the victims, and by dark the news came: The first was a local woman, and the second a young man, a friend of hers. The of the third fatality, the one whose skull had been crushed, was Teena Brandon.

“Brandon?” The locals were perplexed. The barmaid remembered a boy named Brandon living in that house. He had shown up in Humboldt a month or two before and hung out with kids from nearby Falls City. He told people he was from Lincoln, about two hours away. He was small, 5’5″, but good-looking: blue eyes, a wide mouth, heavy eyebrows, and sandy hair combed into a halfhearted ducktail. He wore Western shirts and looked so young they had carded him at the bar: “Brandon Ray Tenna,” his ID had read. “Date of Birth: 12/10/72. Sex: M.”

Playboy Interview: Martin Luther King Jr. (Part One, Part Two), Alex Haley, January 1965

During his time at Playboy, black journalist Alex Haley made his mark through exhaustive interviews with cultural and political titans of the era. His interview with the civil rights leader was the longest interview he ever gave a publication. You’ll be seeing Haley’s name a few times on this list (he would go on to write the book and miniseries Roots).

King: I mean to say that a strong man must be militant as well as moderate. He must be a realist as well as an idealist. If I am to merit the trust invested in me by some of my race, I must be both of these things. This is why nonviolence is a powerful as well as a just weapon. If you confront a man who has long been cruelly misusing you, and say, “Punish me, if you will; I do not deserve it, but I will accept it, so that the world will know I am right and you are wrong,” then you wield a powerful and a just weapon. This man, your oppressor, is automatically morally defeated, and if he has any conscience, he is ashamed. Wherever this weapon is used in a manner that stirs a community’s, or a nation’s, anguished conscience, then the pressure of public opinion becomes an ally in your just cause.

Playboy Interview: Malcolm X, Alex Haley, May 1963

Haley sat down with the other revolutionary leader in the Civil Rights Movement, Malcolm X, at a restaurant in Harlem. In his introduction, Haley notes the interview is both “an eloquent statement and a damning self-indictment of one noxious facet of rampant racism,” and is worth reading for that reason.

Playboy: Is there anything then, in your opinion, that could be done–by either whites or blacks–to expedite the social and economic progress of the Negro in America?

MALCOLM X: First of all, the white man must finally realize that he’s the one who has committed the crimes that have produced the miserable condition that our people are in. He can’t hide this guilt by reviling us today because we answer his criminal acts–past and present–with extreme and uncompromising resentment. He cannot hide his guilt by accusing us, his victims, of being racists, extremists and black supremacists. The white man must realize that the sins of the fathers are about to be visited upon the heads of the children who have continued those sins, only in more sophisticated ways. Mr. Elijah Muhammad is warning this generation of white people that they, too, are also facing a time of harvest in which they will have to pay for the crime committed when their grandfathers made slaves out of us. But there is something the white man can do to avert this fate. He must atone–and this can only be done by allowing black men, those who choose, to leave this land of bondage and go to a land of our own. But if he doesn’t want a mass movement of our people away from this house of bondage, then he should separate this country. He should give us several states here on American soil, where those of us who wish to can go and set up our own government, our own economic system, our own civilization. Since we have given over 300 years of our slave labor to the white man’s America, helped to build it up for him, it’s only right that white America should give us everything we need in finance and materials for the next 25 years, until our own nation is able to stand on its feet. Then, if the Western Hemisphere is attacked by outside enemies, we would have both the capability and the motivation to join in defending the hemisphere, in which we would then have a sovereign stake. The Honorable Elijah Muhammad says that the black man has served under the rule of all the other peoples of the earth at one time or another in the past. He teaches that it is now God’s intention to put the black man back at the top of civilization, where he was in the beginning–before Adam, the white man, was created. The world since Adam has been white–and corrupt. The world of tomorrow will be black–and righteous. In the white world there has been nothing but slavery, suffering, death and colonialism. In the black world of tomorrow, there will be true freedom, justice and equality for all. And that day is coming–sooner than you think.

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The Day Bobby Blew It, Brad Darrach, July 1973

Playboy also did some damn good sports reporting. This piece documents the unraveling of Bobby Fischer in the hours leading up to the 1972 World Chess Championships, a.k.a. the “the Match of the Century.” It’s a long read, but worth it for Darrach’s crisp language and the madness that unfolds.

What the press had, or decided to say it had, was something known for more than a decade to his jealous rivals as “the monster”: Bobby was often discussed as a sort of paranoid monomaniac who was terrified of girls and Russian spies but worshiped money and Spiro Agnew, as a high school dropout with a genetic kink who combined the general culture of a hard-rock deejay with a genius for spatial thinking that had made him quite possibly the greatest chess player of all time. The monster was at best a caricature of Bobby, but he sure made terrific copy.

I sometimes think it is the voice of a man pretending to be an object, so that people won’t notice he is soft and alive and then do things to hurt him. But Bobby is too vital to play dead successfully. Energy again and again short-circuits the robot. Energy like a tiger prowls and glares inside him. Now and then it escapes in a binge of anger. Every night, all night, it escapes into chess. When he sits at the board, a big dangerous cat slips into his skin. His chest swells, his green eyes glow, his sallowness fills with warm blood. All the life in his fragmented body flows and he looks wild and beautiful. When I see Bobby in my mind, I see him sprawled with lazy power at a chessboard, eyes half closed, listening to the imaginary rustle of moving pieces as a tiger lies and listens to the murmur of the moving reeds.

The Man in the Bomb Suit, Mark Boal, September 2005

Journalist Mark Boal embedded with bomb-disposal experts in Iraq to pen this piece for Playboy. It became the inspiration behind his screenplay for the Academy Award-winning film, The Hurt Locker (which was not without controversy).

 He grabs the cap and heads back toward the safety zone, barely noticing a second white bag nearly out of his sight line in a roadside gully. There is a moment now when he doesn’t breathe. He can run for his life and hope to beat this secondary bomb, which an insurgent placed specifically to kill him as he worked on the first one, or he can dive on it and take his chances. He pitches himself into the dirt and reaches for the blasting cap’s wire with shaky hands, the menu of possible outcomes running through his mind. He decides he has to act now; there is no time for deliberation. He pulls it apart, pink wire by pink wire, since all of Baghdad’s bombs seem to be wired with discolored old Soviet detonation cord. Then he breathes.

Playboy Interview: Steve Jobs, David Sheff, February 1985

Before Apple was a household name, Playboy nabbed an interview with the iconic Steve Jobs. It’s full of fascinating tidbits about his life and the early years of Apple.

Jobs: A computer is the most incredible tool we’ve ever seen. It can be a writing tool, a communications center, a supercalculator, a planner, a filer and an artistic instrument all in one, just by being given new instructions, or software, to work from. There are no other tools that have the power and versatility of a computer. We have no idea how far it’s going to go. Right now, computers make our lives easier. They do work for us in fractions of a second that would take us hours. They increase the quality of life, some of that by simply automating drudgery and some of that by broadening our possibilities. As things progress, they’ll be doing more and more for us.

Playboy Interview: Miles Davis, Alex Haley, September 1962

Considered controversial at the time, Haley’s interview provided a window into the soul of the revered jazz musician. It’s an entertaining and insightful read for Davis’s opinions on politics, culture, and inescapably, race. It was also the first interview ever published in Playboy.

Playboy: Did you grow up with any white boys?

Davis: I didn’t grow up with any, not as friends, to speak of. But I went to school with some. In high school, I was the best in the music class on the trumpet. I knew it and all the rest knew it — but all the contest first prizes went to the boys with blue eyes. It made me so mad I made up my mind to outdo anybody white on my horn. If I hadn’t met that prejudice, I probably wouldn’t have had as much drive in my work. I have thought about that a lot. I have thought that prejudice and curiosity have been responsible for what I have done in music.

Playboy: What was the role of the curiosity?

Davis: I mean I always had a curiosity about trying new things in music. A new sound, another way to do something — things like that. But man, look, you know one of the biggest things that needs straightening up? The whole communication system of this country! Take the movies and TV. How many times do you see anybody in the films but white people? You don’t dig? Look, the next movie or TV you see, you count how many Negroes or any other race but white that you see. But you walk around in any city, you see the other races — I mean, in life they are part of the scene. But in the films supposed to represent this country, they ain’t there. You won’t hardly even see any in the street crowd scenes — because the studios didn’t bother to hire any as extras.

Negroes used to be servants and Uncle Toms in the movies. But so much stink was raised until they quit that. Now you do have some Negroes playing feature parts — maybe four or five a year. Most of the time, they have a role that’s special so it won’t offend nobody — then it’s a big production made like that picture is going to prove our democracy. Look, I ain’t saying that people making films are prejudiced. I can’t say what I don’t know. But I see the films they make, and I know they don’t think about the trouble a lot of colored people find with the movies and TV.
A big TV network wanted to do a show featuring me. I said no, and they asked me to just look at a show featuring a big-name Negro singer. No, I ain’t calling no names. Well, just like I knew, they had 18 girls dancing for the background — and every one of them was white. Later on, when I pointed this out to the TV people, they were shocked. They said they just hadn’t thought about that. I said I knew they hadn’t. Nobody seems to think much about the colored people and the Chinese and Puerto Ricans and Japanese that watch TV and buy the things they advertise. All these races want to see some of their own people represented in the shows — I mean, besides the big stars. I know I’d feel better to see some kids of all races dancing and acting on shows than I would feel about myself up there playing a horn. The only thing that makes me any different from them is I was lucky.

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TOP IMAGE: Hugh Hefner celebrating Playboy's 50th anniversary. (Photo by Denise Truscello/WireImage)