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.
* [[EvenEvilHasStandards Even Jerkasses Have Standards]]: 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.
* {{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]].
* LeaningOnTheFourthWall: During the skating competition and Lisa tallies the number of Homer's schemes at 300, Marge notes she thought it was 301. Lisa quickly shushes her.
* TakeThat: Another dig at 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 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]].