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 SimmonsThe 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.
8. Bill O’ReillyThe Guest: I think I summed up my thoughts on Bill O’Reilly fairly well by spending a week making
7. Michael RichardsThe 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.
6. Paris HiltonThe 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.
5. John McCainThe Guest: A lot more press was made by McCain’s
4. Harmony KorineThe 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!
3. Harvey PekarThe 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.
2. MadonnaThe 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.
1. Crispin GloverThe 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.
When not collecting moments we'd rather forget, Michael is head writer for and co-founder of Those Aren't Muskets!