The most uncomfortable Letterman interviews ever

In many regards, David Letterman is the perfect antidote to the airless celebrity interview. During his long, legendary tenure as a late-night talk show host, he earned a reputation for keeping guests on their toes, occasionally insulting visitors, taking pleasure in puncturing their pretenses, and cracking plenty of jokes at their expense. Letterman even admitted as much during a Justin Bieber interview in 2012: "That's what I do," he laughed. "I make people feel uncomfortable." 

Of course, Letterman has also fallen victim to plenty of guests who went out of their way to be openly confrontational, provocative, and gleefully obnoxious. Madonna tossed the F-word around fourteen times during her awkward 1994 appearance. River's Edge actor Crispin Glover narrowly avoided karate kicking Letterman in the face during a berserk 1987 interview. And let's not forget the time Cher called Letterman an "a**hole" during her late night debut in 1986.

Here's a closer look at some of David Letterman's most uncomfortable interviews during his TV tenure on Late Night with David Letterman (1982-93) and the Late Show with David Letterman (1993-2015).

​Madonna vs. Dave: Who was more insufferable?

New life goal: Participate in a televised interview that's so legendarily awkward, People magazine feels compelled to commemorate the broadcast's 20th anniversary, calling it "the most-censored network talk show episode in history." 

Madonna's March 1994 appearance on the Late Show finds the star at her most experimentally insufferable. To be fair, Letterman isn't exactly in fine form, either. He introduces Madonna as an artist who's "sold over 80 million albums … and slept with some of the biggest names in the entertainment industry." (This inspires an aghast Paul Schaffer to shout: "She's your guest!") As Madonna takes the stage, she hands Letterman a balled-up pair of her panties. She also chomps and sucks on a cigar, says "f**k" fourteen times, and compares a microphone to a particular part of the male anatomy. Right before cutting to commercial, she asks Letterman if he's wearing "a rug." Oh, and she also refuses to leave the stage, prompting aggravated folks in the audience to shout, "Get off!"  

Eventually, she does, which is a merciful move. After she leaves, Letterman quips: "Coming up in the next half hour, Mother Teresa is going to drop by." And then, one more zinger: "Oh, I see we've been canceled … there is no show tomorrow night."

Letterman to Paris Hilton: 'So how was jail?'

In October 2007, hotel heiress Paris Hilton made an appearance on the Late Show as part of some unofficial image-rehabilitation tour. Back in civilization after serving 23 days in jail, Hilton hoped to use the segment to hock her fragrance, Can Can, but Letterman clearly wasn't interested in playing the interview safe. 

After putting her at ease with small talk about the differences between Los Angeles and New York, Letterman asks the question on the tip of everyone's tongue: "How'd you like being in jail?" He also inquires about the quality of prison cuisine, so Hilton discusses "jail mystery meat." Letterman is also curious if her time in the clink led to any weight-loss milestones. Hilton is clearly displeased that Letterman is steering the interview down this particularly shady road (i.e. "Have your friends treated you differently since you've been out of the slammer?") She eventually insists, "I'm not answering any more questions about it," reminding Letterman that she's there to promote her clothing line, movie, and perfume. 

Letterman does not relent. When an audience member shouts, "We love you, Paris!," Letterman asks, "Is that somebody you met in prison?" He finally eases up when Hilton resorts to sad-little-girl posturing, telling Letterman he's hurting her feelings. To make amends, he spritzes Can Can in the air, says it's "not too bad," and then pretends to drink greedily from the bottle.

​Letterman somehow makes you feel bad for Justin Bieber

It would seem David Letterman is apparently not a fan of body art, nor is he particularly fond of Justin Bieber. When the Biebs breezed onto Letterman's show in June 2012, the curmudgeonly talk-show host gave him considerable grief for some new ink. "Well, tell me that's the last one," Letterman grumbles, in oddly paternal fashion. As Today reported, things went from merely uncomfortable to all-out intense when Letterman grabs hold of Bieber's arm and starts meddling with the singer's new "Believe" tattoo, prompting Bieber to yelp in pain: "Aye, aye, aye! This is brand new!"

The awkwardness doesn't end there. Letterman advises Bieber not to "go nuts" and completely cover himself in tattoos "like the Sistine Chapel… It's too much!" Tellingly, Bieber responds, "I'm not going for the Sixteenth Chapel." Letterman seizes on the gaffe right away: "Canadian high school!"

In March 2013, more salt was poured onto the wound when Bieber's ex, pop star Selena Gomez, visits Letterman to promote the film Spring Breakers. The talk-show host recounts his awkward Bieber interview thus: "The last time he was on, he and I got into a conversation, and he said something, and I said something, and he said something, and I said something, and I made him cry." Gomez mordantly responds: "Well then, that makes two of us." 

​Michael Richards was sorry. You'll be, too.

Talk about a switcheroo. Anyone who tuned in to watch Jerry Seinfeld's interview with David Letterman in November 2006, was instead treated to a blazingly awkward apology from Michael "Kramer" Richards, who appeared via satellite from Los Angeles.

Richards had just made an unthinkable and career-defining gaffe, spewing out a litany of racist slurs during an ostensible stand-up comedy routine at the Laugh Factory in Los Angeles. During his Late Show apology, Richards claims he "said some pretty nasty things to some Afro-Americans," a term that prompts some audience members to cackle awkwardly. ("Stop laughing, it's not funny," says a tired-sounding Seinfeld.) A dazed, glassy-eyed Richards later notes: "I'm hearing your audience laugh and I'm not even sure that this is where I should be addressing the situation." He adds that he's "really busted up" over the whole mess. Richards apologizes to "the blacks, the Hispanics, the whites… everyone that was there that took the brunt of that anger." He claims he needs to do some "personal work," chalking up the meltdown to having "a bad night." 

Following the appearance, Entertainment Weekly essentially reviewed the apology, calling it "extremely uncomfortable to watch." Meanwhile, The Washington Post said it "took on a Krameresque spin." 

Farrah Fawcett talks and talks and talks...

It was all extraordinarily strange. In 1997, Farrah Fawcett paid a visit to Letterman's talk show on the heels of a much-touted Playboy cover and a Pay-For-View show coyly titled Farrah Fawcett: All of Me. Unfortunately, David Letterman didn't seem to get much of Fawcett at all, because she appeared to be completely out of it.

She apologizes to Letterman for being late, saying there "were people, lots of people." Later, she tries telling a story that involves a road, a wall, and "the thing." She also appears temporarily transfixed by the fake backdrop of Manhattan behind Letterman's desk and confesses: "I really thought I was looking out the window… because I've never been here before." Elsewhere in the segment, Fawcett drinks the water out of Letterman's coffee mug as the audience whoops.

Fawcett later said all this strangeness was a "performance," and longtime boyfriend Ryan O'Neal claimed she called him in tears after the show. In his book, Both of Us: My Life with Farrah (via The Hollywood Reporter), O'Neal said Fawcett was "attempting to play the part of the ditsy bunny thinking it would be a clever way to promote the magazine." 

Cher calls Letterman an 'a**hole'

It took four long years to convince Cher to appear on Late Night, but the "Believe" singer finally relented and made her first of several appearances in May 1986. It's an achingly awkward segment right out of the gate. Letterman tells Cher she smells "terrific," and even asks what fragrance she's wearing. "Is this as good as it gets?" Cher wonders. A disgruntled Letterman pointedly asks what a better line of questioning might be. "I don't know because I've watched this show," Cher answers, somewhat menacingly.

Letterman asks why it took so long for her to appear on his show, and she comes clean. She says it's because she thought he was an a**hole." The crowd alternately whoops and boos, and Letterman laments, "You know, I think a lot of people feel that way about me, though." 

Elsewhere in the segment, Letterman asks Cher to show off her tattoos. He's noticeably distant and distracted, which prompts Cher to ask: "You okay?" A flustered Letterman answers, "I don't know … that 'a**hole' comment … You're the first person to call me that in person…" 

Speaking at a concert in March 2017, Cher said she only made the appearance because producers agreed to pay a $28,000 hotel bill that she'd managed to rack up (via the Daily Mail). 

Crispin Glover: A master class in cringe

In July 1987, actor Crispin Glover appeared on Late Night and kicked up enough free-floating anxiety to blow a hole through the space-time continuum. From the moment Glover saunters onstage in a bizarro fright wig, tight pinstripe slacks, platform shoes, and kooked-out glasses, you know the interview is being transmitted from the dark side of the crystal. 

In a sing-song voice, he tremulously reads excerpts from an L.A. Weekly article that disparages him, prompting Letterman to ask sidekick Paul Shaffer: "Is this the first time you've seen another guy drown? Is this the first time you've watched a guy die?" (Incidentally, he's referring to himself, not Glover.) The situation escalates when Glover challenges Letterman to an impromptu arm-wrestling match ("I'm strong!") and then commits wholeheartedly to a freewheeling karate kick that narrowly avoids hitting Letterman in the face. ("I can kick!" Glover warbles.) That's the last straw for Letterman: "I'm gonna go check on the Top Ten… I'll be back," he says, leaving the stage. 

Glover has remained tight-lipped about what prompted his dazzling tour-de-force freakout, telling Letterman in a giggly follow-up appearance a few weeks later that he "wanted it to be this interesting kind of a thing." (Mission accomplished!) 

​Andy Kaufman really put his neck out

Legendary comic Andy Kaufman appeared as a guest on Late Night with David Letterman on several occasions, and every appearance was pretty uncomfortable in one way or another. That time he appeared on the show disheveled and shellshocked, asking the audience for money? Uncomfortable. Also awkward: The 1983 bit where Kaufman hugged audience members and gushed about how much he loved his parents, who made a surprise appearance on the show: "This is my mommy and daddy," Kaufman told the crowd.  

But if we had to name Kaufman's most uncomfortable Letterman appearance, we'd have to go with the 1982 episode in which Kaufman gets knocked right out of his chair (and, in fact, knocked right off the whole stage) by wrestler Jerry Lawler. Kaufman was already wearing a neck brace, no less! Keep in mind, the comedian was referring to himself as the world's first "Intergender Wrestling Champion" at the time. 

The scuffle was big news, but in truth, there was "never any real animosity" between Lawler and Kaufman, and the moment was "just almost like improv," Lawler told Film Fad in 2014. "I loved it when Andy Kaufman would come on," Letterman told NPR in 2015. "It was just fantastic and unusual and the audience never knew whether he was serious."

Joaquin Phoenix's perplexing performance art

In February 2009, Joaquin Phoenix put his own awkward spin on Andy Kaufman's prankish performance art. During his interview with Letterman, the usually clean-cut actor wanders onstage looking like a cross between a hobo, a cult leader, and late-career Jim Morrison. (A bemused David Letterman compares the new aesthetic to the Unabomber.)

Turns out, the dazed and mumbly appearance was part of a lengthy publicity campaign for the industry satire I'm Still Here, a mockumentary co-directed by Casey Affleck that imagined Phoenix abandoning acting to pursue a new career as a hip-hop artist. "David Letterman was not in on the joke," Phoenix told Playboy in 2014 (via the Daily Mail.) 

The following year, Phoenix apologized to Letterman in another appearance, saying: "I hope I didn't offend you in any way." Letterman replied, "Oh, no, no, no. I was not offended. … I'm telling you, it was so much fun. It was batting practice, you know what I mean?"

Letterman to Harvey Pekar: 'Shut the f**k up'

During his second appearance on NBC's Late Night with David Letterman, comic book writer Harvey Pekar managed to seriously rile the host. The July 1987 segment begins chummily enough, with Letterman thanking Pekar for featuring him on the cover of Volume 12 of American Splendor. He notes that Pekar seems altogether more "relaxed," "contented," and "laid back" than the first time he guested.

Turns out, Pekar wasn't feeling "laid back" at all. He reveals that he'd been offered his own talk show, but ultimately turned it down: "You get co-opted," he notes, pointedly. "You can't do anything serious. And it's a drag to go on night after night doing simple-minded bull***t." After a commercial break, Pekar launches into a tirade about NBC and General Electric. "This is very bad manners," Letterman tells him. "This is very, very inappropriate." After another commercial break, Letterman successfully regains control of the show, saying, "You're a guest in my house, so shut the f**k up. You show up to my house and you sneeze in the hors d'oeuvres." 

The squirmy awkwardness continued when Pekar returned to the show in August 1988. He went on another one of his spiels, inspiring an irate Letterman to snap: "What you're saying is not true … this is not the place to say it." Letterman later calls American Splendor "your little Mickey Mouse magazine … your little newsletter." 

Let's all take a moment to collectively cringe.