10 of the Most Fascinating ‘Playboy’ Interviews

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Playboy magazine is known for its sexy centerfolds and covers, but the gentleman’s glossy has a long history of publishing short stories and interviews with notable personalities. The eternal joke that people read Playboy for the articles is really true. The magazine’s archive reveals a collection of deeply personal and insightful conversations with filmmakers, musicians, and other cultural figures. We’ve highlighted ten that share profound and fascinating moments from pop culture and American history.

Miles Davis, 1962

The interview that started it all for Playboy was with jazz legend Miles Davis. By 1962, the musician had struggled with a heroin habit, toured Paris, and released a series of albums with collaborator Gil Evans. Alex Haley, the journalist responsible for some of the magazine’s most famous interviews, was sent to speak with Davis. Some of the dated language is cringeworthy, but Davis is passionate and candid as he shares his views on race and American culture. The musician had a reputation for being “flinty and truculent,” but his softer side appeared when proudly mentioning his wife, Frances. He also discusses the difference between audiences in Europe and the U.S. “In this country, it’s more following of personalities,” he shares. But it’s Davis’ thoughts on race and prejudice that will stay with you for some time to come, as he concludes: “This whole prejudice mess is something you would feel so good if it could just be got rid of, like a big sore eating inside of your belly.”

Stanley Kubrick, 1968

Playboy is probably the last place you’d expect to read an interview with the reclusive Stanley Kubrick, let alone an interview that covers metaphysics, philosophy, and the nature of God. The conversation centers on Kubrick’s 2001: A Space Odyssey, which was released several months prior.

The first thing you’ll notice while reading is that speculation about Kubrick’s themes and symbolism isn’t a new. Last year’s documentary Room 237 discussed some of the wild perceived meanings in The Shining. Back in 1968, interviewer Eric Norden was pressing Kubrick about the same things in his space epic.

“You’re free to speculate as you wish about the philosophical and allegorical meaning of the film,” Kubrick responded, “And such speculation is one indication that it has succeeded in gripping the audience at a deep level, but I don’t want to spell out a verbal road map for 2001 that every viewer will feel obligated to pursue or else fear he’s missed the point.”

We also love Kubrick’s dig at New York, specifically against the group of critics who called 2001 dull:

“New York was the only really hostile city. Perhaps there is a certain element of the lumpen literati that is so dogmatically atheist and materialist and Earth-bound that if finds the grandeur of space and the myriad mysteries of cosmic intelligence anathema.”

You can read part of the interview here, or purchase it for a mere dollar.

Bette Davis, 1982

The grande dame of cinema spoke to Playboy about the nature of celebrity and her famously sassy reputation. “If you don’t dare to be hated, you’re never going to get there. To be an uncontroversial actor is nothing to aim for,” she mused to the magazine.

She also spoke about controversial issues:

“I believe abortion is better than having 10,000,000 children you can’t support… When I was a child, born in 1908, education taught you that your destiny was to marry and have children. Just because you’re a woman — but that is not your destiny. There are many great women who were just never meant to be mothers, that’s all. We are improving this way enormously.”

And she chimed in about her idol status amongst the gay community:

“Homosexuals are probably the most artistic and appreciative human beings, who worship films and theater… Generally, homosexuals are very appreciative of serious work in the arts, so it’s highly complimentary to be someone they choose.”

Read an interview excerpt here, or purchase it.

Gene Siskel and Roger Ebert, 1991

The banter between film critics Gene Siskel and Roger Ebert is endlessly charming in this 1991 interview. The cineastes playfully griped about Siskel’s lack of technical prowess, and their strengths and weaknesses. We’re treated to a story about Robert Mitchum smoking weed and discover that the men made a point of not socializing in order to save their best commentary for the camera. We also find out that Woody Allen, Mel Brooks, Michael Caine, Dolly Parton, and Meryl Streep ranked as some of their favorite stars to interview. Prepare to miss two of filmdom’s finest.

Martin Luther King, Jr., 1965

If you only read one interview on our list, please make it this one. The civil rights leader sat down for an in-depth talk about the movement. He addresses claims of extremism, and shares poignant stories about his boyhood and the people he encountered along his journey for freedom. A passage about the many threats to his life is absolutely heartbreaking:

“If I were constantly worried about death, I couldn’t function. After a while, if your life is more or less constantly in peril, you come to a point where you accept the possibility philosophically. I must face the fact, as all others in positions of leadership must do, that America today is an extremely sick nation, and that something could well happen to me at any time. I feel, though, that my cause is so right, so moral, that if I should lose my life, in some way it would aid the cause.”

King concludes the interview with a moving and beautiful statement that is all the more powerful since the anniversary of his “I Have a Dream” speech just passed:

“I subject myself to self-purification and to endless self-analysis; I question and soul-search constantly into myself to be as certain as I can that I am fulfilling the true meaning of my work, that I am maintaining my sense of purpose, that I am holding fast to my ideals, that I am guiding my people in the right direction. But whatever my doubts, however heavy the burden, I feel that I must accept the task of helping to make this nation and this world a better place to live in — for all men, black and white alike.”

Steve Jobs, 1985

Joshua Michael Stern’s Steve Jobs biopic is in theaters, but this 1985 interview with the Apple founder makes a case for staying home and reading about Jobs instead. The year Jobs was forced out of Apple and started NeXT Computer, he sat down with the magazine for a fascinating talk about his hopes for the future and the early days of the Internet. He also possibly defined Apple’s model for success when asked about his thoughts on newer tech companies taking over from the old guard:

“That’s inevitably what happens. That’s why I think death is the most wonderful invention of life. It purges the system of these old models that are obsolete. I think that’s one of Apple’s challenges, really. When two young people walk in with the next thing, are we going to embrace it and say this is fantastic? Are we going to be willing to drop our models, or are we going to explain it away? I think we’ll do better, because we’re completely aware of it and we make it a priority.”

Vladimir Nabokov, 1964

On the author’s writing rituals:

“I never learned to type. I generally start the day at a lovely old-fashioned lectern I have in my study. Later on, when I feel gravity nibbling at my calves, I settle down in a comfortable armchair at an ordinary writing desk; and finally, when gravity begins climbing up my spine, I lie down on a couch in a corner of my small study. It is a pleasant solar routine. But when I was young, in my 20s and early 30s, I would often stay all day in bed, smoking and writing. Now things have changed. Horizontal prose, vertical verse, and sedent scholia keep swapping qualifiers and spoiling the alliteration.”

On Nabakov’s “obsessive attention” to words in Lolita:

“For my nymphet I needed a diminutive with a lyrical lilt to it. One of the most limpid and luminous letters is ‘L.’ The suffix ‘-ita’ has a lot of Latin tenderness, and this I required too. Hence: Lolita. However, it should not be pronounced as you and most Americans pronounce it: Low-lee-ta, with a heavy, clammy ‘L’ and a long ‘o.’ No, the first syllable should be as in ‘lollipop,”’ the ‘L’ liquid and delicate, the ‘lee’ not too sharp. Spaniards and Italians pronounce it, of course, with exactly the necessary note of archness and caress. Another consideration was the welcome murmur of its source name, the fountain name: those roses and tears in ‘Dolores.’ My little girl’s heart-rending fate had to be taken into account together with the cuteness and limpidity. Dolores also provided her with another, plainer, more familiar and infantile diminutive: Dolly, which went nicely with the surname ‘Haze,’ where Irish mists blend with a German bunny — I mean a small German hare.”

John Lennon and Yoko Ono, 1981

Conducted a year before his death, this interview with the couple took place during the recording of their collaborative album, Double Fantasy. A good portion of the talk is Lennon defending his relationship with Ono. “Nobody controls me. I’m uncontrollable,” the musician scoffed. “Of course, it’s a total insult to me… ” Ono added.

Lennon’s fire continued when asked about a Beatles reunion:

“It can never be again! Everyone always talks about a good thing coming to an end, as if life was over. But I’ll be 40 when this interview comes out. Paul is 38. Elton John, Bob Dylan… we’re all relatively young people. The game isn’t over yet. Everyone talks in terms of the last record or the last Beatle concert… but, God willing, there are another 40 years of productivity to go. I’m not judging whether ‘I am the Walrus’ is better or worse than ‘Imagine.’ It is for others to judge. I am doing it. I do. I don’t stand back and judge… I do.”

Timothy Leary, 1966

Read on for pages and pages about sex and LSD. The interview was conducted the same year that Leary founded his “religious” organization, the League for Spiritual Discovery, in an attempt to make LSD legal. It was also the same year that the LSD was made illegal in the United States, including usage in scientific research.

Ayn Rand, 1964

We wouldn’t date you if you read Ayn Rand. We’d make an exception for this interview, though — because there’s something perversely entertaining about the juxtaposition of Rand’s surly mug and Playboys cover that month, which reads: “Girls of Russia and the Iron Curtain Countries.” Rand sat for this interview during a period in her life when she was giving some of her most controversial lectures. She was also rallying for Barry Goldwater during the 45th presidential election.