Top 10 Most Awkward Letterman Interviews

on 16 September 2010 in Slideshows


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10. Drew Barrymore When Drew Barrymore comes bounding on stage sans bra bearing a gift of flowers for Letterman, there is no indication of what you’re in store for. After a relatively tame conversation about Drew’s recent appearance at a club where she stripped off for a ‘performance piece’, she bravely offers Letterman a sneak peak and jumps up on his desk giving him a full frontal flash. Unlike the Courtney Love incident though, it’s a very hot moment which Letterman thoroughly enjoys, taking down the details of the aforementioned club. Letterman you old dog! Unfortunately the audience don’t get to see Drew’s goods, and it goes back to tame-city after that.

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    10. Drew Barrymore When Drew Barrymore comes bounding on stage sans bra bearing a gift of flowers for Letterman, there is no indication of what you’re in store for. After a relatively tame conversation about Drew’s recent appearance at a club where she stripped off for a ‘performance piece’, she bravely offers Letterman a sneak peak and jumps up on his desk giving him a full frontal flash. Unlike the Courtney Love incident though, it’s a very hot moment which Letterman thoroughly enjoys, taking down the details of the aforementioned club. Letterman you old dog! Unfortunately the audience don’t get to see Drew’s goods, and it goes back to tame-city after that.

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    9. Harvey Pekar The typically neurotic New Yorker Harvey Pekar was the inspiration for the central character in American Splendor- a film about a frustrated cartoonist working in a dead-end office job, proved too much for Letterman’s patience. Considering Pekar’s last appearances on Letterman, the producers had a good idea of the train wreck the interview would be. Pekar is on the offensive the whole time, while Letterman’s producers gleefully rub their hands together and superimpose a thought-bubble containing donuts next to Pekar’s head- a mortal sin against a guest on any chat show. As it gets progressively worse, Letterman actually bans Pekar from the show, and they stumble to the end with Letterman looking as though he’s been sodomised with the large end of a microphone. Tough break.

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    8. Paris Hilton Filmed just after she rolled out of jail, this interview is probably the most merciless display of facetiousness Letterman has ever shown to a guest, which most people, besides the Hilton clan, had no qualms about. But even still, it’s difficult to watch without squirming in your seat due to the sheer brutality of Dave’s line of questioning. It’s clear she wasn’t invited on the show to talk about perfume or her new musical, instead Letterman gets straight to the point asking “how do you like being in jail?” adding “and they locked up your friend Nicole too”. I'm not sure if they rehearsed the interview, but you've got to be pretty stupid not to expect Letterman to dig into you after being in jail for a DUI. Like, derrr.

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    7. Courtney Love It was 2004 that this glorious interview took place, and it’s a glimpse of Courtney Love in a less than lucid state, looking like she had just been hit by a steam roller, revived roadside and sedated, before having a paint gun apply her make-up and shuffled onto stage. With constant threats of terrorising the audience with her sunken chest, Dave can do little but try and make some sense of what she’s saying, but he mostly just laughs uncomfortably, looking around for the next ad break. He must be getting used to this by now; the producers have probably created a protocol for 'unruly and unmanageable' guests. “What is the nature of your life these days?” he asks, which doesn't elicit the desired response from Love. After baring her tits once more, she yells at the audience “Did I breast feed? Did I breast feed?!” For her daughters sake, I hope to god she didn't. Check out the madness below:

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    6. Harmony Korine You can’t help but feel sorry for Harmony Korine- a shy and geeky budding filmmaker who isn’t used to being on the other side of the camera. Korine’s 1995 appearance on Letterman as a 19 year old marks the release of his first feature film 'Kids'-a brutal documentary-style film based on the lives of drug-taking street kids. Dave’s description of Harmony as “pleasantly odd” doesn’t exactly set the bar very high, but when he sees the way Korine is dressed he asks if the “skate park was closed”...very funny grandpa. When the poster child for edgy, unrelenting indie films calls his brutal movie “a really amazing blockbuster” it tweaks Letterman’s ‘funny bone’, and like a bored unneutered dog, he doesn’t let go until the he’s squeezed every last drop of humour from it. The awkward highlight has to be a 4.02 when Harmony offers Letterman one of his own jokes, eliciting many sideways glances and arched eyebrows from Letterman. What a bully.

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    5. Farrah Fawcett After the success of Charlie’s Angels, the not so angelic Farrah Fawcett became one of those washed-up celebrities who spent way too much time in tanning oil next to their kidney-shaped pool, getting botched plastic surgery to try and reverse the effects of sun damage. But there is a point when it all stops looking fun and you see how pathetic and sad they have become- this is where the interview sets off. Fawcett appears unhealthily thin and in some sort of substance-enhanced glassy-eyed state. She talks about her fans and New York, whilst giggling and looking around the studio at Paul Shaffer, probably surprised to find that he is, in fact, a real person. You can tell that Letterman has no idea what to make of this, but he goes with it anyway. The real awkward highlight is when she explains how she hasn’t celebrated her 50th birthday yet, but struggles to form a meaningful sentence amidst the cackling laughter from the audience.

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    4. Madonna This is Madonna when she was at her obnoxious and sexual peak, around the time she released the goth-inspired ‘Frozen’- before rodeo Madonna, ballet-class Madonna and before her face became plastic surgery’s ground zero. Like a number of other guests, Madonna is aware of Letterman previously making jokes in fairly poor taste about her sex life and refuses to play nice, making it a very uncomfortable 20 minutes of barely- disguised insults, bleeped-out profanities from Madonna and awkward silences as Dave prays for an ad break. You just know it’s going to be bad when in the first 5 minutes of the interview Madonna calls Letterman a ‘sick fuck’ as he tries to convince Madonna to kiss an audience member.

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    3. Michael Richards Michael Richards is like that awesome uncle who lets loose at parties and introduces you to Frank Zappa, but then one time, he gets a bit too loose and you realise he’s actually a racist old bastard who still calls African-Americans ‘blacks’ as a plural (‘The blacks did not appreciate my racist tirade of abuse’). Why Kramer, WHY?! Unfortunately Jerry Seinfeld’s attempt to smooth things out in a letterman interview was not the best avenue for a serious apology, which the ensuing ten minutes of awkwardness will attest to. The audience is already laughing even before Richards says a word, while Seinfeld unconvincingly pleads to the audience ‘Stop laughing, it’s not funny’. But it is. It’s seriously funny, and probably the best possible payback Richards got for ruining our love affair with Kramer.

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    2. Joaquin Phoenix The current release of I’m Still Here has done little to put perspective on the status of former actor Joaquin Phoenix, who was at the height of his hip-hop stoner period when he appeared incognito with full beard and sunglasses on Letterman. Phoenix appears withdrawn and uncomfortable- a big change compared to his last visit, where he was still charming and funny, telling a story about a mouse in his house that he had given a name. Before Phoenix comes on, Letterman sings his praises and that of the recent film Two Lovers he had just appeared in. He begins by commenting on his change of appearance particularly his new beard, making Phoenix ‘feel weird about it’. After an awkward silence of about 10 seconds, Letterman asks “what can you tell us about your days with the Unabomber?” which does not go down well. Phoenix attempts a comeback saying “what do you have them on? What are you gassing them with?” alluding to the fact that the audience is laughing indiscriminately at everything. Ten painfully hilarious minutes later, Letterman finishes by saying “I’m sorry you couldn’t be here tonight Joaquin”, which finally gets a laugh out of him. Enjoy the full clip here:

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    1. Crispin Glover It’s not completely clear in this interview whether Crispin Glover is just being his usual insane possibly drug-fucked self, or whether he’s rehearsing for the role of an anxious psychopath who still thinks he’s at Woodstock. In any case it makes for a very entertaining interview, even managing to scare Letterman so much he actually gets up off his chair and back away when faced with a hick kick from Glover’s platform-adorned appendages. Glover rambles through the interview, seeming on the edge of a nervous breakdown, complaining how the press can twist your words around. The audience meanwhile is in hysterics as they yell out “nice shoes!” Even Paul Shaffer won’t touch it, while Dave asks him “is this the first time you’ve seen another guy drown?” He is apparently alluding to himself there, but it could go either way. Glover is back on the show a couple of years later, and although he’s somewhat subdued compared to his previous performance, he isn’t making much sense. The lesson here: never trust an actor with a briefcase.

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