Stephen Colbert on David Letterman

What do Obama and a certain highly acclaimed blond actress have in common? In a meeting of the late night comedy giants, Stephen Colbert reveals the answer to David Letterman—and confesses the challenges of having a president who's, well, cooler than him.

Updated Apr. 25, 2017 11:35AM ET / Published Nov. 20, 2009 2:59AM ET

What do Obama and a certain highly acclaimed blond actress have in common? In a meeting of the late night comedy giants, Stephen Colbert reveals the answer to David Letterman—and confesses the challenges of having a president who's, well, cooler than him.