We see a possible future in which Bart is a grown-up slacker, living with Ralph Wiggum, while Lisa is no less than President of the United States.

Krusty announces his retirement due to interference from network executives and the growing popularity of the big-money game show "Me Wantee", but when Krusty reveals to Sideshow Bob that all of the episodes featuring him have been erased, Sideshow Bob uses Krusty's biggest fan (Bart) to murder him during Krusty's farewell show.

Homer is prescribed medicinal marijuana after getting pecked in the eyes by a murder of crows. While his family and friends worry about the drug altering his personality, Homer becomes Mr. Burns's vice president after cracking up at Burns's antiquated jokes.

During the annual Jellyfish Festival, Ned Flanders realizes that he is lonely and becomes depressed. One night, he meets a beautiful woman, who asks him out on a date. He soon learns that the woman is Sara Sloan, a famous actress. Sloan is charmed by Flanders' wholesomeness, and they continue to date to the point at which she asks that he move to Hollywood. Flanders, worried that Hollywood would conflict with his conservative Christian values, refuses, so Sloan instead decides to stay in Springfield. However, their relationship does not work out, due to his insistence on marriage.

Homer sees a movie about the end of the world and fears the same thing will happen in real life after seeing a chain of random occurrences (celebrities ["stars"] falling from the sky, raining blood, a man in a realistic devil costume) and doing a complicated math equation that predicts the end will come on May 18th, but when the end does not come, Homer discovers a flaw in the equation and ends up in Heaven where he meets God and learns that God is planning The Rapture.

The family is at a church fund-raiser, where Homer tries to ensure his rubber duck onto victory, but Flanders wins the big prize, which he doesn’t want and gives it to Marge. In return Marge agrees to watch Rod and Todd while Ned is attending a left-handed convention. While Marge is spending all her time with the Rod and Todd and trying to let them learn how to be boys; Homer takes Bart and Lisa to a home for former celebrity animals and a monkey kidnaps Bart. Marge’s ability to be a mother comes into question when Ned discovers what she is doing with his boys and the local news covers Bart’s current predicament.

Lisa's friendship with Fat Tony's son Michael prompts mob boss Tony to invite the Simpsons over for dinner. Michael says he'd rather be a chef than take over the family business, but that's before Tony is shot by a rival mobster.