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 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.


Madonna (March 31, 1994)

In the spring of 1994, the Late Show was still clobbering Leno’s Tonight Show in the ratings, and Letterman was in his rightful spot at the top of the cultural heap. So when Madonna came by the show in a willfully bratty mood, the host didn’t even blink. Dropping f-bombs, offering Dave her panties and making lame sexual innuendos, the singer has rarely come across as crassly “provocative” as she did that night. (She later said that the show’s writers egged her on to be as controversial and difficult as possible, in order to make the appearance memorable.) And he made every single second of it comic gold, refusing to be thrown by her stunts and working his slow-burn irritation to perfection. When she weakly tries to zing him on his hair — “Is that a rug?” — he fires back at her severe ‘do, “What is that, a swim cap?” When she tries to extend her visit — “Can’t this just go on and on?” — Letterman snorts, “It seems like it has, don’t it?” Honestly, we would have watched a full hour of these two.


Harvey Pekar (August 31, 1988)

In the early days of Late Night, Letterman made his name aligning himself with cool outsiders — R.E.M., Andy Kaufman — but those relationships weren’t always cozy. Now perhaps best known because of the movie made about him, American Splendor (starring Paul Giamatti), comic book artist Harvey Pekar delivered numerous hostile appearances on the show. The curmudgeon-vs-curmudgeon battle peaked with his 1988 interview, where he went off on General Electric, NBC’s bosses at the time, and called Dave “a shill” for the company. It irritated Dave enough that he vowed to ban Pekar. “I’d rather be liked than thought of as a crazy man,” the late artist told the Los Angeles Times in 1995, “but with Letterman, I’ve been in a situation where you either lay down and let him insult you or you do something about it. Most people keep their mouth shut and let him dump on them. I don’t wanna do that.”


Joaquin Phoenix (February 11, 2009)

Whenever this clip is shown, it’s impossible not to feel bad for James Gray. The indie filmmaker, whose superb 2009 romantic drama Two Lovers starred Joaquin Phoenix, was probably thrilled to get the kind of promotion that a spot on the Late Show would afford his low-budget movie. Instead, Phoenix (and partner-in-crime Casey Affleck) hijacked the appearance for their own project, the faux-documentary I’m Still Here, in which the Oscar-nominated star “quits” acting for a hip-hop career — though Letterman wasn’t in on the stunt. (You can tell from his Unabomber joke, which is biting, terrific and filled with disdain for his catatonic interviewee.) Phoenix returned a year later, sans hobo beard, to apologize. The great irony: Both Two Lovers and I’m Still Here sank like stones — but this appearance will outlive them both.

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