The whole storyline involving Lisa shows many references to The Sound of Music. When Lisa gets told she can be a tutor, she dances on a hill (similar to the opening sequence of the film) and when she introduces herself, Cletus' children walk forward and state their name (a reference to Maria's introduction to the children). Some of the songs they sing are based on songs from the film, including the song performed by Superintendent Chalmers and Principal Skinner, which is inspired by "How Do You Solve a Problem Like Maria?" Lisa sings part of a song resembling "The Sound of Music", and later while showing the children the culture of Springfield sings a song based on "My Favorite Things" and a rehearsal scene in which the children sing a song based on "Sixteen Going on Seventeen". Unlike Simpsoncalifragilisticexpiala(Annoyed Grunt)cious and My Fair Laddy, the episode does not include instrumental songs from the episode during the credits due to copyright reasons from 20th Century Fox.
The relationship Bart shares with his psychiatrist is reminiscent to the way that Tony Soprano and his psychiatrist form a unique bond, with Bart in depression wanting to see her, and the doctor wanting to see more of Bart. Dr. Swanson's psychiatrist also resembles the character of Dr. Elliot Kupferberg from The Sopranos, who was Dr. Melfi's psychiatrist. Peter Bogdanovich plays both roles.
The style of the artwork in the sequence in which Bart tells his classmates a story about a murderous cafeteria worker resembles the work of Edward Gorey. A piece of music is used in this scene that is reminiscent of a piece of Astor Piazzolla's music from the suite "Punta del Este" used in the film Twelve Monkeys. This same music is used later when Bart's psychiatrist sees her psychiatrist. The clip is also comparable to that of Stephen Sondheim's Sweeney Todd.
The video game, Death Kill City II: Death Kill Stories, played by Bart and the psychiatrist is a reference to the Grand Theft Autoseries of video games, notably the city stories prequels (Liberty City Stories and Vice City Stories). The rating for Death Kill City II is "Bad for Everyone," which spoofs the ESRB rating, "E for Everyone".
The ending, with Cletus saying, "Baby, you're the greatest," Cletus and Brandine kissing, the pan to the skyline and moon, with Cletus's face, and the music are all a direct reference to the 50's sitcom The Honeymooners.
Bart says he dreamt his whole family were cartoon characters and their success had led to Fox News. This is what the Simpsons are, which breaks the fourth wall.
Dr. Swanson allowed Bart to play Death Kill City II: Death Kill Stories, which is rated 'Bad for Everyone' and in real life would be rated M (Mature; 17+) or possibly AO (Adults Only; 18+), meaning that it is extremely unsuitable/inappropriate for Bart who is only 10, therefore Dr. Swanson would have faced disciplinary action and possibly dismissal.