Late Night vs. The Man : Wait Wait ... Don't Tell Me! David Letterman sticks it to NBC, before sticking it to NBC was cool.
NPR logo Late Night vs. The Man

Late Night vs. The Man

I've been pretty impressed by the digs Conan and Jay--okay, mostly Conan--have been getting in at NBC this week (a particularly good roundup of the most recent stuff here, courtesy of Gawker). It's always nice to see somebody telling off their boss in public, even better if there's an audience there to laugh at it.
But for real comedic courage in the face of management, it's hard to beat the above: David Letterman's classic attempt to deliver a fruit basket to GE, back in 1986. And hey, that worked out great.