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This one is longish, but fun. William Buckley was a conservative who hosted a PBS show called Firing Line. He was fairly erudite, and on his show he was usually able to intellectually intimidate his debate opponents. But when he had on Noam Chomsky, Buckley was definitely outclassed, and it ‘s fun to watch the two of them parrying, with Buckley clearly in over his head. To Buckley’s credit, he allowed Chomsky onto mainstream television, something that broadcasters then and now were and are loath to do.

Thanks to YouTuber Patrick Steinkuhl