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 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.
** Marge is a very lesser case, she'd rather Bart stay in a house he's miserable and treated badly in by Homer then for him to leave.
* EvenEvilHasStandards: The judge that takes up Bart's case is Judge Harm. Despite being known for her cruelty and harshness, even she feels that Homer is too much of a JerkAss for Bart to be living with him.
* HoistByHisOwnPetard: This is the only episode where Bart returns the favor to Homer. Unlike Homer strangling Bart with his hands, however, Bart 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 [[MoralEventHorizon 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.
* 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.
** WhatCouldHaveBeen: Original drafts of the sketch had Homer lose Bart's commercial money by buying a star that goes supernova and Homer being unable to get the money back, but the Music/MichaelJackson baby-dropping incident happened and, much like ''WesternAnimation/SouthPark'', they changed it at the last minute to reflect this pop culture reference. [[WereStillRelevantDammit Too bad the joke didn't stay fresh]].