For an upcoming charity comedy concert, Bart persuades emcee Jay Leno to hire Krusty the Clown to perform. Appearing with such modern comedians such as Steven Wright and Janeane Garofalo, Krusty's act is an embarrassingly unfunny anachronism. The performance is so disastrous that it drives Krusty to "the bender to end all benders," where he passes out on Evergreen Terrace. Bart takes him into his room, where he is shocked at the quantity of low-grade merchandise bearing his likeness. Bart and Jay Leno's attempts to update his act fall flat, so Krusty decides to retire. At his press conference, his sardonic commentary is well-received by the press, so he goes back into stand-up as a modern, edgy, envelope-pushing comedian. However, when two car company executives persuade him to endorse the Canyonero SUV, he realizes that it's not comedy that he's best at, but "selling out."