Bart gets in trouble for joyriding in a police car, but feels confident he will be let off by Judge Snyder. However, Snyder goes on vacation before ruling his verdict and is replaced with a coldhearted judge named Constance Harm. She accuses Homer of being a negligent father and sentences him to be tethered to Bart. The two are against it at first but later start to bond. Marge however is unable to take anymore of it and slices the tether off of them both. Homer and Marge then go after Judge Harm only to end up sinking her houseboat. Eventually Bart decides to take punishment and is about to be sentenced to 5 year in juvenile hall, only though Judge Snyder returns and dismisses Harm.

Guest star: Jane Kaczmarek and Jess Harnell.[21]

A social worker is assigned to make the Simpson family functional after they get arrested for fighting while playing Monopoly. He helps them learn how to work together and function as a family. The moment is ruined when, Ginger and Amber, the barmaids who married Homer and Flanders while they were drunk in "Viva Ned Flanders", arrive at the Simpsons' home, which outrages Marge.

Bart learns that he was once a child actor in commercials and that all the money earned was spent by Homer. In retaliation, Bart petitions the court to have himself legally emancipated from his parents and moves out of the Simpson house. Bart is initially miserable in his new apartment, but discovers that skateboarder Tony Hawk lives on one of the floors above. He and Hawk become friends, and Bart is content with his new life. Homer apologizes to Bart and requests that he return home. Bart accepts the apology, but tells his family that he is going on tour with Hawk. At an event, Homer speaks to Bart and finally promises Bart that he will never treat him badly again.

Homer becomes obsessed with using new gadgets in his car. One day, he becomes distracted and drives off a pier, losing his driver's license. Unable to use a car, Homer starts to learn the joys of walking. Meanwhile, Marge shoulders the burden of Homer's driving duties and becomes stressed out. One day, as Homer sings about the virtues of walking, Marge accidentally runs him over with her car. Later, as Homer recuperates from the accident, he begins to suspect that Marge is trying to hurt him. They fight and go to see a marriage counselor. The counselor advises Homer to perform one completely unselfish gesture to win Marge back. Homer holds a party with all of her friends and a surprised Marge tells Homer that she loves him.

Bart gets sent to juvenile hall after fooling everyone that there was a marriage concerning him. He encounters a dangerous girl there... He flees with Gina, but then the two are caught by Wiggum.

Lisa does what every little sister has dreamed of - she gets a restraining order put on her big brother. Bart is forced to live in the back garden, but soon realises the joy of communing with nature.

Selma and Grampa embark on a May-December romance, and Bart and Lisa get into trouble with deliverymen over cardboard boxes.

Homer is completing his court-ordered community service when he befriends his supervisor, Chief Wiggum, by offering him one of his sandwiches. Touched by the act of kindness, Wiggum assigns the other convicts unpleasant tasks, but allows Homer to join him at the picnic table. They continue to grow close, but when the Chief gets injured during a botched bank robbery, Homer doesn't come through when Wiggum needs him the most. Meanwhile, Bart becomes addicted to Battle Ball, a Japanese game made up of plastic balls and magnetic cards, and his family and teachers try to help him kick the habit.