The best piece of unintentional humor to come out of NBC’s late night dramedy is probably Jay Leno’s original 2004 announcement that Conan O’Brien would take over The Tonight Show in five years. Funny or Die unearthed the clip, which features Jay deeming Conan the best choice to take over for him, and promising to leave the show with dignity and grace.
“This show is like a dynasty. You hold it, and then you hand it off to the next person,” says Leno, adding that he doesn’t want to see the switch cause the same problems that his earlier battle with David Letterman did. “I don’t want to see all the fighting, and all the ‘Who’s better?’ and nasty things back and forth in the press. So right now, here it is: Conan, it’s yours, see you in five years, buddy.”