With his retirement just days away, one late night fan remembers all the wildest times…

David Letterman has been on the air for longer than I’ve been alive, so to me, his retirement is as eventful as Johnny Carson’s was to my parents. But as a child, watching reruns of Late Night on E! or the current show on CBS, I was drawn to Letterman because he felt like the anti-Carson. He did weirder, conceptual stuff that had this mean edge to it. He had this biting sarcasm that would piss you off in-person were it not so damn funny. In a time of scripted boredom on other talk shows, Dave’s routinely went off the rails, and you could tell he loved starting those fires, even when they sometimes burned him too.

So, as we all say goodbye to the man, I’m ignoring all the hilarious scripted content he’s had on his show for 35 years, and narrowing my focus to the moments when things got a little too real. When even Letterman had to throw up his hands and say “I won’t let you kick me in the face.” And because 10 is a number he’ll always been known for, here are my 10 favorite moments where David Letterman got out of control.

10. Joaquin Phoenix Is A Douche

This one goes so low because it was so obvious at the time what was going on. Comedy nerds like myself knew Phoenix was trying his hand at a Andy Kaufman/Borat fakeout of quitting entertainment to start a rap career, and we weren’t buying it. When he showed up on Letterman in 2009, he was certainly doing a good job acting like a piece of crap, and Dave likely wasn’t in on. The audience certainly wasn’t, as their nervous laughter attests. Ultimately, when the comedy film came out Phoenix had to admit the obvious joke was, duh, a joke, but still, it was nice to see an attempt of the spontaneity the show had in previous decades.

9. Harvey Pekar Isn’t Happy

See now this, THIS is true discomfort. The late Harvey Pekar is a famous name in the world of comics, writing some groundbreaking alternative work in the ’70s, and Letterman had him on mainly because he’s a cantankerous weirdo. Pekar wasn’t in the mood for fun during his final appearance above, which made for a cringeworthy exchange with Dave. Pekar is none-too-pleased with GE buying NBC, what with the company’s war profiteering, nuclear power plants, and general destruction of the planet (still going strong). Harvey was there to air his grievances and basically ignore Dave, which Letterman wasn’t all that happy with, though he does his best to calm down Pekar. It doesn’t work, but hey, a good host does his best in those situations.

8. A Fruit Basket For GE

Speaking of sinister mega-corporation General Electric, when NBC was first bought by the company, Letterman did one of his wonderful man-on-the-street bits and visited their office. He wanted to say hello to his new corporate masters with a fruit basket, but they didn’t want him in the building. GE’s inability to take a joke made for some uncomfortable moments that Dave milked for all they’re worth. If I recall correctly, rumors at the time said GE remembered this stunt when it was time to pick someone to replace Carson.