After finally accepting that his comedic style is outdated, Krusty settles on edgier material: what's wrong with today's crop of stand-up comedians. Guest starring Jay Leno, Steven Wright, Janeane Garofalo, Bobcat Goldthwait and Bruce Baum. Featuring Hank Williams Jr. The name of this episode is very similar to an earlier episode "The Last Temptation of Homer."
Persuaded by Bart to appear at a comedy festival organized by Jay Leno, Krusty the Clown's old-fashioned and dated material fails to impress the crowd when compared with other, more trendy comics also appearing. After going on 'the bender to end all benders', he holds a press conference to announce his retirement, and in short order launches into a bitter tirade against modern-day comics, which the crowd finds hysterical. He is inspired to return to doing low-key events, where he structures a new act for himself as a comic who tells the truth and refuses to sell out to corporate America. Although less marketable and financially successful, he is now credible and trendy. Two marketing executives try to persuade him to advertise the Canyonero, but he initially resists, before succumbing to the lure of money again. He finally admits to himself that it is not comedy that is in his blood; it is selling out.