The Client List (2012)

S1E11 A Day at the Races and a Night at the Opera

After Marty doesn't succeed at his school field day, he feels downcast, prompting Jay to step in and boost his self-esteem. Jay encourages Marty to explore playing guitar and convinces him to participate in the school talent show. Meanwhile, Them Magazine recognizes Jay as "the wittiest man alive," leading Duke to propose a $100 reward for anyone who can keep a straight face during Jay's performance, a plan that doesn't sit well with the crowd.