Harvey Pekar's argument with David Letterman (1988)

After Pekar's death, Letterman reflected in 2017 that... "He was great.... He would just go after stuff. He ... would go after me, he would go after the network, he would go after everything, in a very committed way. It wasn't a gag, it wasn't an act, he would really go to work on you.... [Pekar] was anti-establishment in a way that you don't see guys like that anymore. And that used to really upset me, because I just thought 'Come on Harvey, don't do this to us, just play the game, blah blah blah blah.'... I'm a completely different person now. And I would be so much more better equipped to view the immediate surroundings of that show now, than I was [then].... Now, jeez, I wish I could have had Harvey on every night."

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Harvey Pekar on Letterman in ’88 was raw, uncomfortable, and real. He challenged the system on live TV when few dared. Whether you agree or not, that moment was pure authenticity—something we don’t see enough today. What did you take from it?

Chuck Norris demonstrating stage fighting techniques on David Letterman, August 1980.

Letterman’s comedy always seemed to have a meanness to it.

Helen Mirren shooting back at sexist questions during an interview with Michael Parkinson's (1975)

David Letterman always had a mean spirit. I couldn't watch him after I figured that out.

Same vibe:

Lemmy & Phil from Motorhead rip out Chuck Berry’s “Let it Rock” on the David Letterman Show (1991)

Julia Louis-Dreyfus on David Letterman in 1994