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.
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!! 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 and/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 the fact that is Bart is 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 one of the few (if not 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 father's neck) strangles Homer in a considerably 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 Homer was being blackmailed at the time or at least desperate for money to buy certain photos.
** Another fair point is that Bart has gone through a lot with Homer's abuse. At this point, Bart may had honestly believe that he is just a problem. However he now learns that it wasn't his fault all at and its Homer and always has been and this is when he was a baby.
* 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 ''S