Lisa awakens from a dream about attending the Kennedy Center Honors to find out that Marge wants everyone to help with Spring cleaning. As they tidy up the garage, Lisa and Bart happen upon some old videotapes, one of which reads, “Bart Sad.” The kids put the tape in the VCR and watch a breath freshener commercial featuring Bart as a baby. Bart is shocked and humiliated. When he confronts his parents, Marge assures him that Homer invested the proceeds in a college trust fund. But it quickly becomes apparent that Homer spent all the money. Bart tells Milhouse about the commercial—and his wish to get back at Homer for what he did. Milhouse suggests he contact an attorney. Later, Bart pays a visit to Burns’ lawyer and announces his attention to divorce his parents.

Burns’ lawyer serves Homer with Bart’s emancipation papers. The matter ends up in court, where Homer repeatedly loses his temper. After witnessing the outbursts, Judge Harm rules in Bart’s favor…and awards the boy half of Homer’s paycheck. When Bart returns home, he packs up his suitcase. An emotional Marge prepares a week’s worth of meals for her son and smothers him in kisses. As Bart pulls away in a taxi, Homer runs after him, insisting that he’ll be back. But Homer drops to the ground and begins to sob. Bart gets a loft in downtown Springfield. It isn’t long before he begins to feel unsafe. When he hears some strange noises, he leaps out of his sleeping bag and jumps into an elevator, calling for his mommy. The elevator takes him upstairs, where he finds Blink 182 hanging out in a cool loft. Skateboarding legend Tony Hawk strikes up a conversation with Bart…and Bart declares it’s the greatest night of his life. Tony Hawk points out that a nearby Web cam is recording the party. As it turns out, Homer, who is surfing the net, hears Bart’s words.

As the judge set up visitation rights, the Simpsons head for downtown Springfield to see Bart and his loft. When Lisa compliments Bart on his furniture, Homer loses his temper when he realizes he paid for everything…and starts strangling Bart. Later, at dinner, Bart tells Homer and Marge that he’s leaving for six months to join the Skewed Tour, a traveling festival of music and extreme sports. Homer begs Bart to change his mind, but Bart explains that he’s already sublet the loft. As the skateboarding competition gets underway, Homer approaches Tony Hawk and asks him if he’s willing to lose the competition to him so he’ll be a hero to his son again. Hawk tells Homer he’ll help out. He gives Homer a high-tech skateboard that creates the illusion the rider has talent. As the pair perform loop-de-loops on the half-pipe, Homer and Hawk’s skateboards battle it out, a la Crouching Tiger, Hidden Dragon. Homer wins the competition…and expects Bart to come back to him. But Bart tells Homer the disagreement was never about Homer being cool, it was over Homer not caring how Bart feels. With some help from Tony Hawk, Homer makes an emotional turn and tells Bart he wants the opportunity to make things right. Bart accepts the apology and returns home.