
After Joaquin Phoenix's (un?)successful foray into the world of drugs, rapping and late night Letterman failures, we thought to ourselves, "Well this sounds familiar." And it wasn't just the anti-comedy of an Andy Kaufman act either. For some reason, Letterman's show in particular seems to turn some celebrities into drooling zombies who Dave can't help but poke fun of. Below, the Best of Letterman Bombs.
Crispin Glover: 1987
The original "fucking with you" performer on Letterman, Glover deserves credit because he fooled everyone, Dave included, into thinking he was a giant, creepy weirdo. And I mean he is, but his whole routine here is just over the top. At the time, no one had any idea of what to make of Marty McFly's dad wearing a wig and giant shoes, looking like he's about two minutes away from having to breathe through a paper bag. David gets pissed because he realizes Glover is fucking with him, and from then on, Dave adheres to the "poke at them, before they can poke at you" principle.
Madonna: 1994
Dave never loses his cool in this interview, although this episode is so notorious as to have its own Wikipedia page for being the most censored network television show in history. Madonna cursed, lit up a cigar and refused to leave the set after her interview. Good thing she's totally cleaned up her act, right guys?
Farrah Fawcett: 1997
Oh, this one is just sad. Farrah is obviously on some sort medication (did they have Ambien back in the 90s?) or maybe accidentally took an E-pill or something, because her pupils are gigantic. And Dave, God bless him, keeps gently fucking with her because she is totally a space-cadet and doesn't seem to know she's on national television. Farrah insisted after the show that this was just her way of joking with the audience, and in a creepy moment of foreshadowing, pointed to actor Joaquin Phoenix as an example of her "style." Well, crazy knows crazy, I guess.
Bill O'Reilly: 2006
In 2006, Bill O'Reilly went head-to-head with Letterman in a two-part interview where the men locked horns on almost every topic. In this clip, O'Reilly starts out on the offense, saying, "Do you want America to lose in Iraq? Easy question," while Dave retorts, "It's not easy for me because I'm thoughtful."
It only gets better from there, with Dave saying, "You're putting words in my mouth just the way you put artificial facts in your head." Maybe the first time we've really just loved David Letterman, instead of feeling neutrally apathetic about the gap-toothed host.
Paris Hilton: 2007
She just wanted to talk about her perfume, Jesus! Why is that ugly old man being so mean to her? Why is he talking about prison! She no want to go back there! Prison bad! Herpes outbreak, painful! Paris hate David. He not hot.

Not on the list but honorable mentions are Harvey Pekar (if Letterman didn't like the American Splendor creator so much, he wouldn't have kept asking him back), John McCain (McCain rolled with the punches too well for it to get awkward), and Drew Barrymore flashing her tits for him for his birthday (reminds me of drunk Meredith from The Office).
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Basically, it's fun sometimes to watch an asshole.
You gotta hand it to the guy. He's been doing what he does best for a really, really, really long time.
ISN'T IT FUNNY HOW THE PUBLICITY MACHINE WORKS?
Joaquin Phoenix quits ‘acting,’ goes on David Letterman to promote (ahem) a barely whispered-about movie, feigns indifference to Dave and the movie Two Lovers and the audience, and even more dangerously, the publicity game itself.
And snap, just like that, this little $12 million “last” movie of Joaquin’s gets more attention than a $12 million media blitz could buy.
La La Land’s legitimate shrink Dr. Drew Pinsky, who’s actually seems pretty level-headed most of the time, voices “grave concern” about Phoenix’s disheveled and flat affect and wonders aloud if the actor isn’t, A) intoxicated on something, or B) experiencing depression.
But if you watch Joaquin closely in the Letterman clip that’s now gone viral, he’s certainly lucid enough to take his own jabs at Dave.
CrabbyGolightly come hither.