23. Sam Waterston Says Things You Should Never Believe in a Trustworthy Manner
An early sign that Colbert was the spiritual descendant of David Letterman, this silly, totally non sequitur bit featured Law & Order's ramrod serious Sam Waterston making ridiculous straight-faced statements in that soothing, confident voice of his. ("It's okay, I've had a vasectomy. I swear.") The whole thing was dreamed up as a response to the actor's Law & Order costar Fred Thompson's ill-advised 2008 presidential campaign. "I think [Colbert's] the funniest man on the planet," Waterston said in 2012, "and also the bravest."