Louis C.K. appeared as the sole guest on Conan last night, in honor of the 20th anniversary of Conan’s debut on Late Night.
Conan and C.K. spent the show reminiscing about their early days of working as comedians together. The best story came from C.K., who told a sad, albeit, hilarious story about hitting on Gwyneth Paltrow at a company Christmas party and getting shot down.
According to C.K., he went up to Paltrow, who was still in the beginnings of her film career, and began to say things to her like “We should just get married.” C.K. said he thought things were going well and remembered saying “I think I’m going to marry this actress and move to California.” Later that night, he made one final attempt to woo her by performing a trumpet solo. Louis, who does not play the trumpet, said the tactic didn’t stir a desirable reaction.