In 1993, mere hours after Conan O'Brien was plucked from The Simpsons writers' room obscurity to take over for Letterman, he went on the Tonight Show. It is a brilliantly awkward, yet endearing, clip that explains why it took Big Red quite awhile to find his Late Night footing.
"If there's anything that's fun to do...it's replacing legends at NBC," Jay Leno.
Perfect.
(by Patrick Sauer) Running Time: 1:54