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My favorite is still Bobcat Goldthwait setting fire to Jay Leno's chair on the old Tonight Show. Jay got so fucking pissed off, and actually took Bobcat to court over it. Gold.
You can't even find the clip of that on the internet, Jay had them never re-air the episode, and so it didn't make it into the youtube era. I just happened to see it that night live.
You can see a small snippet of it on this clip from the Larry Sanders show, but the full thing was amazing
Strangely enough I'm actually currently watching 'The Larry Sanders Show' boxset and just saw the episode when that happened!
I thought that was just part of the Sanders show, didn't realise it actually happened for real on Jay Leno!