Bart learns that a big comedy benefit show in Springfield isn't including Krusty the Clown on the bill. He rectifies the situation by speaking with Jay Leno, organizer of the event. Krusty's appearance at the show goes badly as he tells dated offensive jokes.

Discouraged by his failure at the show, Krusty goes on an all-night bender, winding up passed out on the Flanders's lawn. Bart rescues Krusty and brings him to his room. There, Krusty sees all of Bart's Krusty merchandise and realizes that he should have spent his time over the years honing his act instead of selling out. Bart has Jay Leno over to help Krusty update his comedy, but Krusty's attempts to modernize don't work out. Yet, when he announces his retirement, his tirade against modern comedy has all the reporters in attendance laughing. He decides to give show business another go.

Krusty's new "tell it like it is" image is a hit, and he becomes a popular comedian in Springfield once more. Krusty's new-found credibility is noticed by a couple of ad executives who approach him about endorsing a new sport-utility vehicle. Krusty initially rebuffs the execs, but in the end, he relents. Seeing Krusty as a sellout once more, Krusty's audience turns on him, ending his stand-up comedy comeback.