Letterman vs the World: Dave's 10 Tensest Interviews - Rolling Stone
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Letterman vs the World: Dave’s 10 Tensest Interviews

From Madonna dropping F-bombs to a hobo-bearded Joaquin Phoenix, we revisit the ‘Late Show’ host’s biggest on-air stand-offs

Madonna and David LettermanMadonna and David Letterman

You can't host a talk show for 33 years and have a warm rapport with every single guest. In 1986 when Cher first appeared on Late Night With David Letterman — in a segment that was memorably difficult — she astutely observed, "I see how you deal with your guests. And sometimes it's really great and you seem to like them. And then sometimes, if you don't like 'em, you might as well take a picnic lunch."

Letterman laughed, but he didn't dispute her assessment, and indeed some of his finest interviews have taken place with a palpable tension between guest and host. With that in mind — and a tip of the cap to infamous appearances by Crispin Glover, and Andy Kaufman and Jerry Lawler — here are 10 of Dave's tensest, most awkward interviews. Yes, many of these are well-known, but it's amazing to go back and watch them now: Contentious they may be, but they're also often fascinating, revealing and very, very funny.


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