In mid-1962, Playboy founder Hugh Hefner was given a partial transcript of an interview with Miles Davis. It covered jazz, of course, but it also included Davis’s ruminations on race, politics and culture. Fascinated, Hef sent the writer—future Pulitzer-Prize-winning author Alex Haley, an unknown at the time—back to glean even more opinion and insight from Davis. The resulting exchange, published in the September 1962 issue, became the first official Playboy Interview and kicked off a remarkable run of public inquisition that continues today—and that has featured just about every cultural titan of the last half century.

To celebrate the Interview’s 50th anniversary, the editors of Playboy have culled 50 of its most (in)famous Interviews and will publish them over the course of 50 weekdays (from September 4, 2012 to November 12, 2012) via Amazon’s Kindle Direct platform. Here is the interview with Howard Stern from the April 1994 issue.