Homer goes to jail after a fight at the Springfield St. Patrick's Day parade. When he attempts to bail out, Homer meets Lucky Jim and Wolf the Bounty Hunter and starts to believe he could also hunt criminals. Homer the Bounty Hunter hooks up with Ned Flanders to create his crime fighting team, but when Homer's new attitude gets the best of him, Flanders gets upset. Meanwhile, without the family's knowledge, Marge begins working at a sex bakery.
Bart takes a job at a country club retrieving golf balls in order to purchase a much needed cell phone. While at the course, Bart watches Denis Leary and friends playing a round.
Lenny wins the lottery and invites the Simpson family to a party at a nice hotel. Bart meets Simon Woosterfield, who is a member of the richest family in Springfield.
First, Homer kills celebrities so they can be exploited free-of-charge. Next, robots duke it out in Springfield, and in "It's the Grand Pumpkin, Millhouse," Lisa goes with Millhouse to a pumpkin patch to await the appearance of the Grand Pumpkin. But when the pumpkin finally appears, it goes on a violent rampage to avenge all the pumpkins tortured in the name of Halloween.
The Simpson family takes a road trip to a cabin in the woods. Upon their arrival, a series of flashbacks show Homer and Marge's early married years. They recall the first time they met with Flanders and Maude twenty years prior, where Flanders insisted the then-unmarried couple stay in separate rooms.
Lisa discovers her amazing talent for doing crossword puzzles and becomes an expert cruciverbalist, and she soon enters a citywide crossword puzzle tournament.
The Simpson family takes a trip to the Mapple Store at the Springfield Mall where Lisa get her very own Mypod and Bart interrupts an announcement from Steve Mobbs with his own voiceover, causing pandemonium to break loose in the store.