1988 Bentsen-Quayle

Lloyd Bentsen had seen it coming. Dan Quayle had been working John F. Kennedy into his stump speech as a way to defuse the inexperience issue. He was bound to fall back on it in the debate, and when Quayle did, Bentsen, who had served in the House of Representatives with a young JFK, was ready with perhaps the best single pre-cooked put-down in televised debate history. "I knew Jack Kennedy. Jack Kennedy was a friend of mine. And, Senator, you're no Jack Kennedy." George Bush won the election, but Quayle never recovered. (Which may say something about the relative importance of vice-presidential candidates.)