Playboy, Howard Cosell, Gene Siskelr, Roger Ebert, Rush Limbaugh, Howard Stern, Bob Novak, Rowland Evans, Bill O'Reilly, Michael Moore, Donald Trump, Mark Cuban, Simon Cowell, Keith Olbermann & Michael Savage 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 outspoken personalities.