In 1962, future Pulitzer Prize–winning author Alex Haley sat down with jazz musician Miles Davis for what would become an institution of American journalism—the Playboy Interview. To celebrate the Interview’s 50th anniversary, Playboy has 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, a glimpse at our conversation with The Daily Show host from the March 2000 issue.

“Preconceived notions are invalid. With accountants the big gag is that they’re boring. But I’m sure there’s a hang-gliding accountant out there who knows how to play the drums and fucks like a champ. I’m sure there’s an accountant somewhere who comes home late at night drunk, sticks his dick in the butter, laughs his ass off and goes, ‘If they only knew.’”

“Reporting news is a huge responsibility. It has to be taken more seriously. Bobcat Goldthwait had a great joke about the guy who videotaped the Rodney King beating. His joke was: “Put down the camera and help him!” He’s right. News isn’t a Discovery Channel documentary where you’re not supposed to feed the apes because that would be messing with the journalistic credibility of your documentary. It’s real life. News shows do, at times, affect the real news with their coverage.”

“Here’s what I think of when somebody has the nerve to ask me what it’s like to step over the line with a joke: What about a news program that shows a guy whose wife just got blown up in an accident? Right away they’ve got a camera at his house, in his face, and the correspondent asks, “How does it feel?” Then they show you the body. What answer will we get that’s not some variation of “shitty”? What right do we have to know how that guy feels after losing his wife? There are times when I think, Man, this news guy would do a report from inside an open wound if he could.”

“Some of us are optimists, some are pessimists. Some see the glass half full, some see the glass half empty. And some are sitting on shards of glass and trying to pick them out of their ass.”

To read the interview in its entirety on your Kindle App, Kindle Fire or Kindle Touch, click below.

*Or read the interview with access to all Playboy interviews on iPlayboy.*