Lisa dreams of being honored as one of three great Americans, only to be waken by Marge's vacuum. Marge and the rest of the family have begun spring cleaning. Bart finds a box of old videotapes. He and Lisa start watching the tapes that are boring them, until Lisa finds a tape labeled "BART SAD." They put in the tape, which features an episode of Perfect Strangers and a commercial for a product that fights bad breath for babies. The baby featured in the ad is none other than Bart, leading Lisa to realize the tape should have been titled "Bart's Ad." The baby in the ad is referred to as "Baby Stinkbreath," which opens Bart up to name calling by his siblings. Bart confronts his parents about the ad and Homer tells him he was going to tell him on his "death bed." They tell him he enjoyed making the commercials and he made a lot of money that Homer invested in a college trust fund. Homer confesses that he used the money to buy back incriminating photos. Bart demands the return of his money; Milhouse suggests that he get a lawyer. He finds a lawyer and tells him he wants a divorce from his parents. In court, Judge Harm renders her verdict, Bart is emancipated and half Homer's salary is to go to Bart. Bart moves out and into a loft apartment. His first night alone he is scared by a rat and runs to the elevator that takes him up instead of down. The doors open to a loft apartment that contains skateboard ramps, "skate boarding legend Tony Hawk" and the band "blink - 182" playing live in the corner. The family comes to visit Bart at his new home, where Bart appears to be living the good life. Homer makes a plea for his return, but Bart tells them he is taking off for six months to go on the "Skewed Extreme Sports Tour." At the Springfield stop of the tour, Homer talks Tony Hawk into losing to him in a skateboarding contest so that Homer might win back Bart's affection. When wins the contest, Bart informs him it was about being cool, it was really about Homer not caring about how he felt. With a bit of advice from Tony Hawk, Homer makes an apology and gets a lucrative commercial endorsement for "Viagra-Gain" which allows him to repay Bart, who returns home.
Elenco: Dan Castellaneta , Julie Kavner , Nancy Cartwright , Yeardley Smith , Hank Azaria , Harry Shearer .