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Letterman's 9 Most Hilariously Awkward Moments

David Letterman may not be the greatest late night host ever (sorry, nobody's ever going to top Craig Ferguson), but there’s one type of interaction in which Letterman absolutely shines: dealing with people he has no respect for. If Letterman thinks the guest isn't worth his time (and he'll let you know within the first thirty seconds), you'd be well advised to set the Tivo and microwave a bowl of popcorn, because shit is about to get hilariously awkward.

I used to think it was his becoming old, crotchety and possibly senile that gave rise to this bizarre streak of gut-busting faux pax, but the videos gathered below prove without a doubt that Letterman's been a dismissive prick since the very beginning. Well played, sir.

9. Richard Simmons

The Guest: Simmons isn’t the kind of guy who demands a lot of respect to begin with. It’s like how in nature, animals sometimes display bright colors as a warning that they’re dangerous. But, you know, the opposite.

The Tipping Point: At the beginning, you can almost tell yourself Dave’s genuinely faking interest. Sure there’s some sort of dangling tray fouling up the segment, but he’s not about to let that ruffle him. Unfortunately Simmons use of the phrase “go-go kart” is an offense he apparently can’t let slide by without comment.

The Highlights:

  • The simpering sarcasm that passes for Simmons’ anger, like a dandelion head bursting in your face on a crisp Spring morning.

  • The fact that Letterman mocks Simmons’ clothes is made all the more poignant when Simmons stands up a second later to reveal a lovingly sequined glitter shirt handmade in Dave’s honor.

  • The explosion. It’s an excellent enough moment to make me wish all TV segments ended with minor appliance fires. It would sure liven up the local news.

  • 8. Bill O’Reilly

    The Guest: I think I summed up my thoughts on Bill O’Reilly fairly well by spending a week making a five-minute video of him being an irresponsible prick. Dave’s feelings are probably along the same lines, which meant this clip was destined for Youtube greatness.

    The Tipping Point: After Dave spends a good thirty seconds thoughtfully articulating his fairly complex standpoint in response to Bill’s browbeating, emotionally provocative, sound bite of a question, Bill interrupts him to repeat the same question, but louder. It’s at this point you can see Dave realizing that they are no longer in the realm of reasoned debate, and responding accordingly.

    The Highlights:

  • Since this is the first time I’ve seen O’Reilly from an angle besides in-my-face, it’s also the first time I became aware that he has a troll-like hunchback. For a comedy blogger, this is excellent information to acquire.

  • The fact that CBS cut the video off at the exact height of Dave’s superiority over Bill. The only way they could have encapsulated the interview better would be to change their call letters to ZNG! If you want to see the whole excruciating interview, feel free to click this phrase right here.

  • 7. Michael Richards

    The Guest: As you may recall, Michael Richards went on an ethnically-themed tirade at a comedy club in the mid-00’s. In case watching the video of that wasn’t uncomfortable enough for you, here he is stammering out an awkward apology on national television.

    The Tipping Point: This one’s not Dave acting disrespectful as much as the whole damned situation being as uncomfortable as a long car ride with the grandparent who’s “of a different era.” Still, the fact that Dave calls Richards out when he seems to blame the black guys in the audience because they “heckled him” lets you know he’s not a big Kramer fan.

    The Highlights:

  • When Jerry Seinfeld, ostensibly one of the funniest people in the world, turns to the tittering audience and says “stop laughing, it’s not funny” in a way that irresistibly triggers another wave.

  • At one point, Richards questions whether the Letterman show was the right place to apologize, takes a dig at the audience, and then at Dave for making jokes about the situation. He then settles the issue definitively by sawing his hand through the air, going “ya-ta-ta!,” and sliding through the door of Jerry’s apartment to borrow food.

  • I know this one lags in the last third, but watch that part anyway, because I swear to God none of the words Richards puts together amidst collar-tugging silences coalesce into anything that means anything at all in any language. This is followed by some gibberish he cribbed from Maya Angelou to make a perfect bullshit sandwich (open faced).

  • 6. Paris Hilton

    The Guest: On some level, Paris Hilton must be aware that society by and large considers her an imbecile. It’s what she’s built her empire on. That, and her weird half-closed left eye. So it’s in keeping with her nature that of all the nights she could have appeared on The Late Show, she chose the week after she was released from prison. Thanks to Dave, she’s not likely to make that mistake again.

    The Tipping Point: Letterman clearly had this ambush planned from the very beginning. Basically the first words out of his mouth are “so…prison.” From about 0:50 on, it’s just a long tragic slide into a lecture from your Dad.

    The Highlights:

  • Letterman’s continuous recanting of facts about the case, as if Paris might have forgotten the details of her own life while designing a new fragrance.

  • When Paris, basically placid throughout the entire interview, finally asks aloud if they can stop talking about her jailtime, and Dave responds by changing gears from “coyly invasive” to “brutal, cutting sarcasm.”

  • About six minutes in, when you defy all your natural tendencies by actually starting to feel bad for Paris Hilton.

  • 5. John McCain

    The Guest: A lot more press was made by McCain’s failure to appear on The Late Show than when he actually did show up, but there’s not a lot more awkward than watching him trying to explain himself to several million swing voters while being openly mocked.

    The Tipping Point: When McCain is forced to utter the three words that can kill a Presidential campaign—“I screwed up”—and Dave laughs the laugh of a man who just warped the course of American history with his stupid TV show and unwillingness to let anything go.

    The Highlights:

  • McCain reveals his true feelings about Keith Olbermann at precisely 0:43.

  • And somewhere between 1:04 and 1:20, he officially becomes a sad old man.

  • During the course of the interview, McCain implies that Dave is a hack, overpaid, and a torturer, and says that he can use spy satellites to find out the details of his phone conversations. It’s nice to know that even in our ultra-PC world, the powerful can still threaten to have someone killed for fucking with them.

  • 4. Harmony Korine

    The Guest: Harmony Korine is the heroin-chic avant garde writer/director who helped bring us Kids and Gummo, two mock-documentaries about how terrible stuff can be if you’re poor, HIV-positive, addicted to drugs, or just leading a miserable, fucked up life. I know what you’re thinking: laughs ahoy!

    The Tipping Point: 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 and asks if the “skate park was closed,” you know Dave’s officially shifted into crotchety old man mode and is fixin’ to drive us all the way to Awkwards-ville at eight miles an hour with the blinker on.

    The Highlights:

  • When the poster child for edgy, unrelenting street film calls his brutal movie about the lives of cat-murdering white trash “a really amazing blockbuster.” Somehow, I can’t imagine the Armageddon crowd movie hopping to go check out Gummo.

  • Harmony’s constant wiping of his eyes and strange choking noises could either be inappropriate laughter at some imagined private joke or bitter tears for all the suffering in the world. Either way, I want to buy some of his drugs from him.

  • The part where Elliot Smith makes a surprise appearance and—oh, nevermind, that’s still Harmony.

  • 3. Harvey Pekar

    The Guest: Robert Crumb collaborator and central character of the film American Splendor, Harvey Pekar here manages to somehow be uglier and more obnoxious than Paul Giamatti putting all of his considerable talents towards being ugly and obnoxious.

    The Tipping Point: It’s pretty apparent from Harvey’s otherappearances on the show that Letterman’s Producers booked him for the sole purpose of causing a TV train wreck that channel surfers would be forced to stop an ogle. So when Letterman literally bans Harvey from the show, he’s essentially saying “hosting my own show is not worth the ordeal of talking to this man for four minutes.”

    The Highlights:

  • At 3:20, when Letterman’s staff officially decide to deploy the nuclear warhead of talk show interviews, the superimposed thought balloon. Either that, or Harvey’s brain has become so powerful that it can materially manifest donuts (although I’m not sure I’d be willing to eat a donut that came out of Harvey Pekar’s head).

  • The comments below the video, wherein people almost unanimously support Pekar as a “working class hero” and denounce Letterman as a “smug hypocrite.” I’m not saying I disagree with the latter, but really? A working class hero? John Lennon would not approve.

  • 2. Madonna

    The Guest: Before cowgirl Madonna, Kaballah Madonna, and Guy Ritchie-ruining Madonna, there was filthy sex goddess Madonna. Here, she punishes Dave for making jokes about her promiscuity and unseemly nature by graphically detailing her sex life and cursing like a sailor.

    The Tipping Point: Really, it’s Dave’s fault. He just had to push her. And after he spends the opening minute of the interview trying to get Madonna to kiss an audience member, she signals the beginning of his penance by calling him “a sick fuck.” From the look on Dave’s face, he knows things are only going to get worse from there.

    The Highlights:

  • Madonna gives Letterman her underwear and tries to get him to smell them, likens the boom mic to a big black dick, and turns every possible instance of sexual suggestiveness into a joke about her aching vagina. The whole interview is essentially your high school theatre class. Or possibly a Cracked article.

  • Madonna calls “untrue rumor” an oxymoron, which implies that she believes all rumors to be true. Therefore, I’d officially like to start the rumor that Madonna is only adopting kids so she can eat them when the End Times come. Then she and Alanis Morisette will hang out in a ranch house and compose ill-informed songs about linguistic concepts.

  • When she accuses Charles Barkley of “not understanding the meaning of friendship,” marking the most unlikely celebrity beef of all time.

  • By 13:20, they actually settle into a pretty awesome Abbot and Costello-ish routine culminating in one of Dave’s best zings of all time (at 14:55). The rest is entertaining enough that it actually made me want to see them do a national tour where they just talk to each other until they’re so full of hate that the show falls apart.

  • 1. Crispin Glover

    The Guest: Twenty years later, debate still rages in the lamer corners of the Internet as to whether this is footage of Crispin Glover, world’s best actor, or Crispin Glover, world’s highest man. Fake or real, it’s worth watching if only to see Paul Shaffer with slightly more hair.

    The Tipping Point: Whatever tipping point preceded this display of drug-induced self-reproach and pale nerdy flexing happened long before the interview took place. My question is how they did a rehearsal interview without realizing the guy was on a mountain of angel dust big enough to have been the remains of a wildfire in heaven.

    The Highlights:

  • Always on the cutting edge of fashion, Crispin perfectly models his six-inch platform shoes by directing a high kick directly at Dave’s face.

  • About halfway through, Glover proves that an incredibly high man can still read Variety. That’s right before he says “I’m strong,” then flexes muscles large enough to make you think “oh wow, he actually is kind of strong,” and then “David is in grave danger.”

  • Seriously, what the hell was in that case? Human eyes? Victorian flatware? I really want to know.

  • When not collecting moments we'd rather forget, Michael is head writer for and co-founder of Those Aren't Muskets!

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