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.
- Abusive Parents/Jerk Ass: 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.
- 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 Jerk Ass 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. Homer's own ascension into fortune was ruined by Bart's stupidity.
- Leaning on the Fourth Wall: 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.
- Take That: Another dig at Michael Jackson, 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.