In the (episode advertised as the) 300th episode, Bart discovers that he was once a child star in a string of embarrassing commercials, but when Homer reveals that all of Bart's money went to buying back incriminating photos, Bart petitions the court to have himself emancipated and moves to a loft apartment next to Tony Hawk and Music/Blink182.
!! Tropes:
* AbusiveParents[=/=]JerkAss:
** While Homer was never a saint to begin with, this episode takes a more serious view on his callous and abusive behaviour, resulting in Bart deciding to emancipate himself.
* AmbiguousSyntax: Lisa finds the video tape titled "Bart Sad", which intrigues her, and so, she puts it in the VCR. However, when she finds a commercial starring Bart as a baby, she realizes that this should have said "Bart'''[='=]'''s Ad"
* ArtisticLicenseLaw: Bart's emancipated from his parents at the age of 10--in real life, you have to be 14 to 17 to be legally emancipated from your parents or legal guardians.
** EveryoneHasStandards: Judge Constance Harm is the one takes up Bart's case against his dad. Despite being known for her cruelty and harshness, as well as acknowledging that Bart's technically too young to be emancipated from his family, even she feels that Bart's probably better off living on his own than being forced to live with a JerkAss like Homer.
* ContinuityNod: When Judge Harm rules that half of Homer's salary is to be given to Bart, Homer complains that half his salary is already going to [[Recap/TheSimpsonsS10E10VivaNedFlanders his Vegas wife]].
* HoistByHisOwnPetard: This is the only episode where Bart returns the favor to Homer. Unlike Homer strangling Bart with his hands, however, Bart, being too small to wrap his hands around his fathers neck, strangles Homer in a more violent manner: using Homer's '''belt'''.
* {{Hypocrite}}: It's somewhat hard to take Bart's complaints of Homer cheating money from him seriously given the endless cases throughout the show that he has lost, exploited, tricked or plain out stolen large sums of money from Homer (and the rest of his family). [[Recap/TheSimpsonsS2E2SimpsonAndDelilah Homer's own ascension into fortune was ruined by Bart's stupidity]].
** To be fair, Homer did this to Bart since the latter was a baby--also, it's implied that he was being blackmailed at the time or at least desperate for money to buy certain photos.
* IThoughtItMeant: When Homer and Marge receive a subpoena from Bart's lawyer and Bart explains that he wants to be emancipated from them (mainly Homer), Homer initially assumes that it means Bart wants to be a girl (presumably thinking that emancipation involves a sex change). Lisa explains to him that in this situation, "emancipated" means that Bart would be declared a legal adult and be able to move out and live on his own despite not being 18 yet (the age that a person is usually considered a legal adult).
* LeaningOnTheFourthWall
** During the skating competition and Lisa tallies the number of Homer's schemes at 300, Marge notes she thought it was 302. Lisa quickly shushes her. This references how the episode is actually the 302nd Episode, but was advertised by Fox as the 300th.
** Bart says he doesn't remember doing a commercial...while munching on a Buttterfinger.
* ShoutOut: Upon arriving at his new loft, Bart enthusiastically throws his baseball cap in the air, announcing that he's "gonna make it" a la ''Series/TheMaryTylerMooreShow''... only for it to get ripped into a million pieces by the ceiling fan.
* StockAudioClip: During the [[ "anger management problems" scene]], the exact same audio of Homer saying "Why you little...!" is used three times in a row.
* TakeThat: Another dig at Music/MichaelJackson, this time of his infamous public showing of his baby to the media. This episode parodies that with Homer pulling the same stunt during Bart's babyhood...only he winds up dropping him.
* WhosOnFirst: When Bart goes to the Blue-Haired Lawyer and explains that he wants to be emancipated from his parents, the lawyer seems to go "you WHAT?!" Bart explains himself again, but the lawyer explains that he understood Bart the first time and that he was just calling for his secretary--a woman who happens to be named "Yuwa."