10 of the Most Fascinating ‘Playboy’ Interviews

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.”