The Playboy Interview: Late-Night Talkers

About the Series: 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 past half century.
To celebrate the interview€s 50th anniversary, the editors of Playboy have assembled 13 compilations of the magazine€s most (in)famous interviews€"from big mouths and wild men to sports gods and literary mavericks. Here is our collection of 12 interviews with the most engaging nighttime hosts.