Krusty is persuaded by Bart to appear at a comedy festival organized by Jay Leno. His old-fashioned and outdated material fails to impress the audience when compared with the more trendy comedians also appearing. After reading a critical review of his act in the press, Krusty decides to go on a "bender to end all benders" and a montage sequence shows him getting drunk. After Bart finds him passed out on Ned Flanders' front lawn, he enlists the help of Leno to clean him up. Krusty holds a press conference to announce his retirement and in short order launches into a bitter tirade against modern-day comedians. The audience finds Krusty's rant hysterically funny and he subsequently announces his return to comedy.
Krusty is inspired to return to doing low-key events, where he structures a new image for himself as a stand-up comedian who tells the truth, criticizes commercialism, and refuses to sell out to corporate America. He also changes his appearance, sporting a dark sweater and tying his hair in a ponytail. Observing his newfound popularity, two marketing executives try to persuade Krusty to endorse a new sport utility vehicle called the Canyonero. Although he tries to resist, he eventually succumbs to the lure of money. After promoting the Canyonero at a comedy performance in Moe's Tavern, he is booed off stage by the patrons. He finally admits to himself that comedy is not in his blood and selling out is. The episode ends with an extended advertisement for the Canyonero, as Krusty and Bart leave Moe's tavern in Krusty's new SUV.