There’s more to Dave Letterman than that famous gap-toothed smile: the late night talk show host has been on air making audiences laugh for 25 years, first as host of Late Night with David Letterman on NBC, and then on CBS’ Late Show.


Over the years Dave has had a laundry list of famous (and infamous) guests. The legendary comedian recently spoke to Rolling Stone about his life behind the Late Show desk, as well as some of his more memorable moments.


"I remember being very intimidated by Madonna," Dave tells the magazine, "because I didn’t know anything about popular music, and I didn’t know whether we should even worry about her after her first appearance." He goes on to say that the "material girl" was less than pleased with his jokes about her sex book, and let him know her displeasure on the show.


"Now we find out that she’s outraged, and she comes on and was unpleasant and all of that. I think she kind of realized that she had underestimated the impact of doing that," he says.


In typical Dave style, he rolled with the punches.


"But now that seems so long ago that we’re both like, ‘Who cares?’ Then the other fact is that it’s all artificial," he adds. "We’re all pretending. We’re putting on a show and trying to be cute and trying to say funny things, and we don’t really mean much of it. "


Dave also clears up rumors around the whispered about rift between himself and Oprah Winfrey, saying he hopes things are good with them now.


"I think that she, like anyone would, got tired of me making jokes about her"


As for his career in general, the bespectacled host seems very upbeat.


"I like the people I’m working with. It’s a completely different show than it used to be, it’s more host-friendly than it ever has been. . . . I’m not working as hard as I used to,"  he jokes. "All I have to do, really, is pick out a tie and sit down."


Check out the rest of the interview in Rolling Stone, on stands Thursday.

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