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A good roast requires a willingness to make fun of yourself, which is why Donald Trump bombed at this year's Al Smith dinner. Obama, on the other hand, had an equal-opportunity approach to burns at the 2008 event.
Funniest moment: When a Michael Bloomberg burn turned out to be a Bill Clinton jab: "Michael Bloomberg is here. The mayor recently made some news by announcing that he's going to be rewriting the rules and running for a third term, which caused Bill Clinton to say, 'You can do that?'"