David Letterman has never been a fan of George W. Bush. During the former president's time in office, Dave mocked his use of language, his intelligence, his policies and his demeanor. Now, after his successor has proven to be a smart, deliberate and skillful speaker, Letterman has found a way to mock all of those aspects of Bush at the same time: Comparing him to Obama.
In a segment he started when the new president took office called "Cool/Not Cool" Dave looks at some similar situations the two men found themselves in (basketball photo-ops, White House press conferences, commencement addresses) and compares their actions/words to see who ends up looking cool and who ends up looking idiotic. You'll never guess which way it plays out.