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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.

Justin Bieber

Justin Bieber (June 21, 2012)

As Letterman got older, his profound lack of interest in youth culture became more and more obvious. Take, for example, this interview with Justin Bieber, which starts off pleasantly enough. But as it rolls along, the host's clear indifference to the Canadian phenom creates a noticeable, entertaining tension. By the time the Beeb incorrectly refers to Michelangelo's Vatican painting as the Sixteenth Chapel, well, there's no stopping Dave from mocking the poor kid. Bieber tries to smile his way through the chat, but when he finally tells Letterman that he feels uncomfortable, the host cackles and delivers a comeback that could be the master's mantra: "That's what I do: I make people feel uncomfortable."

Farrah Fawcett

Farrah Fawcett (June 5, 1997)

"You're making fun of me," the former Charlie's Angels star told Letterman during her first appearance on his show. Yes, but what made the segment delicious — and also more than a little sad — was how deadpan Dave was while getting his licks in, and how unaware she seemed to be. On to promote a Playboy cover and a pay-per-view special, Fawcett seems distracted, harried, incoherent — and everybody in the studio knows it but her. The interview is a litany of disasters: Fawcett fumbles through a rambling story about Central Park, a stage manager trips during the broadcast. But the highlight/lowlight has to be the moment when she stops what she's saying to stare at the fake backdrop behind Letterman and exclaim, "Wow…," briefly thinking it's the real New York City skyline. Fawcett, who died of cancer in 2009, claimed in 1999 that her behavior on the Late Show was a "performance." It sure didn't feel that way in the moment.

Lindsay Lohan

LAS VEGAS - APRIL 9: In her first interview anywhere since November 2012, actress Lindsay Lohan talks about her upcoming trip to rehab, her guest star roles in the series "Anger Management" and film "Scary Movie 5" and more when she visits the LATE SHOW with DAVID LETTERMAN, Tuesday, April 9 2013 (11:35 PM-12:37 AM, ET/PT) on the CBS Television Network. (Photo by Jeffrey R. Staab/CBS via Getty Images)

Lindsay Lohan (September 4, 2013)

Even Letterman's most awkward interviews can be compelling thanks to Dave's ability to ask meaningful, albeit uncomfortable questions to guarded guests. When Lindsay Lohan came on to promote Scary Movie 5, she was already far gone into her tabloid nightmare. (The actress was scheduled to start a rehab stint the following month.) The conversation is ragged and somewhat combative — Letterman tries to read her a list of jokes the staff had written about her addiction problems — but there's also a weird tenderness to their exchange. Surprisingly, the host was able to draw out the vulnerability and charm that once made her seem like the next big movie star. Viewers tuned in hoping for a train wreck; instead, they got to see one of the more tender exchanges between Lohan and a TV personality not known for pulling punches or acting paternal.

Cher

Cher (May 22, 1986)

Best known as "The Interview Where Cher Calls Dave 'An Asshole,'" this visit was four years in the making, as Letterman and his staff had been trying to get the actress-singer to come on Late Night from its inception. Visibly nervous, the host begins clumsily starting off by telling her she smells nice ("Is this as good as it gets?" she asks) and never really recovers. After a bit of small talk, she says that her reluctance to come on was due to the fact that he allegedly could be "an asshole" to guests; Letterman then flails to come up with questions and frets aloud how many people secretly think he's a creep. Cher clearly has a ball toying with the inexperienced, intimidated host, and the 16-minute interview ended up becoming both an endearingly awkward exchange and her first of many visits to the show.

Harmony Korine

Harmony Korine (October 17,1997)

Once Letterman went over to CBS (and his show moved up an hour), he started attracting a greater consistency of A-list movie stars and directors. The one downside is that when he came across a dyed-in-the-wool indie auteur, the host's genial tone didn't mix so well with his guests' studied cool. The clearest example of this tension was Letterman's interactions with screenwriter and director Harmony Korine, which peaked on this 1997 appearance to promote the defiantly peculiar Gummo. At one point, the young filmmaker's fumbling, halting half-answers finally drive Dave to turn to the camera and confide, "You're just sitting there in your house, eating Cheetos. You think this is easy, don't you?" In 2013, Letterman revealed to Spring Breakers star James Franco that the reason Korine was later banned from the show was that Dave caught him riffling through fellow guest Meryl Streep's purse backstage.

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Paris Hilton (September 28, 2007)

The knock on Letterman is that he’s “too mean” — a charge that’s ridiculous since what makes Dave great is that he cuts through the nicey-nicey nonsense of most chat shows. That said, he was spectacularly cruel to Paris Hilton during this fall 2007 appearance. The celebrity wanted to promote her latest fragrance, and Letterman couldn’t have cared less. After a couple disinterested questions about New York versus Los Angeles, the host gets right to it: “How’d you like being in jail?” Needling her about her short recent prison stint for driving with a suspended license, Letterman never lets up, even after Hilton curtly insists she’s not going to talk about it anymore. (Thankfully, not before he asks, “Have your friends treated you differently since you’ve been out of the slammer?”) Dave later apologized, but we owe him many thanks for not playing ball with a blatant image-rehabilitation project — as well as for that moment when the host drinks her dumb perfume.

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Bill O’Reilly (October 27, 2006)

Most of Letterman’s contentious interviews stem from bizarre behavior from his celebrity guests. But when the host of The O’Reilly Factor visits Dave, the tension derives entirely from the two men’s vast political differences. Their highlight clash was in October 2006 — and in hindsight, this exchange is a perfect time capsule of Bush-era America as the country remained bitterly divided about Iraq and confronting terrorism. Increasingly angry at O’Reilly’s rhetoric and blustering righteousness, Letterman memorably snarls, “You’re putting words in my mouth, just the way you put artificial facts in your head.” And even at the end, he’s throwing zingers, mixing self-deprecation with incisiveness: “I’ll just end up by saying, I have no idea what I’m talking about. But I don’t think you do, either.

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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.

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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.”

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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.