Main story plot: Bart finds out that there is a better prankster than him in Springfield and is determined to find out who it is (as Skinner won't tell him). Side story: Marge needs to start living a healthier lifestyle and serving healthier food in order to stay in her "mommy and me" group.
Story #1: Bart is planning his prank list for the school year and thinks he is top dog of the prankster world. His life is turned upside down when he discovers that he isn't the best at school pranks. Turns out the best prankster was 19-year-old Andy Hamilton (voiced by Jonah Hill). Andy's biggest prank (filling the school's swimming pool with worms and trapping Skinner in the pool for three days) back in his day completely changed Principal Skinner and Groundskeeper Willie's lives.
Bart finds Andy and is immediately amazed at how "successful" his hero is. Andy is 19, unemployed, lives with his mom, and pulls pranks on people all day. Lisa makes Bart realize that Andy is a loser and this gets Bart thinking about his own life. Bart gets Andy a job with Krusty as his second assistant but Andy only lasts a whole day and quits. Bart tells Andy how he should want more with his life so Andy gets his job back with Krusty. Bart goes to Krusty's studio to visit Andy and fears that he is up to his usual prankster self. Turns out Krusty liked all of Andy's pranks and hired him to write for his show.
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