Original airdate: November 22, 2009
The premise: Bart is shocked to find out he’s not Springfield Elementary’s greatest prankster, an “honor” held by twenty-something manchild Andy Hamilton (voiced by Jonah Hill). Feeling bad for his poor lot in life, Bart attempts to help Andy get a job. Meanwhile, Marge comes under fire from her fellow Springfield mothers for serving their babies unhealthy snacks, so she resolves to go completely organic.
The reaction: This is another one of those episodes that really illustrates how the writers don’t know how to write for Bart anymore. He feels jealous of this Andy character, then enamored by him, then for some reason he’s goaded by Lisa into thinking he’s a loser and wants to help straighten his life out. Remember the great Bart fantasies showing him as a wandering drifter, betting all his money at a casino and losing, or becoming a literal monster from testing food additives? He’s ten years old, he thinks those are awesome depictions of adulthood. Why the fuck does Bart care about this guy’s life? By the second half, he’s like this stern parent figure to Andy, a role that just doesn’t make sense for Bart at all. And another tension-free ending that they try to play up for drama. You know as soon as you see that worm truck that it’s all part of Krusty’s act, but we’re stuck watching two minutes of them pretending it’s not. As for the B-story, it’s pretty much a collection of the most basic health food jokes (Buying organic is expensive! Carrying a reusable grocery bag is effeminate!)
Three items to note:
– We see right before Andy’s master prank, Skinner was actually a laid back, cool dude? That just doesn’t compute with me. Also, how could he have NOT seen the entire fucking pool was filled with worms as soon as he walked outside?
– Andy waxes on about how back in his day, they couldn’t film their pranks for YouTube. It feels like such an odd line, considering Bart has been ten since 1987. Seeing the Simpsons utilizing new technology has always felt weird to me. It took a while to get used to them just using a computer.
– At Marge’s Mommy meets, we see baby Gerald and his equally unibrowed mother. He’s Maggie’s infant arch-nemesis, but I guess you gotta work with the characters you got. Though there’s one token random mother and child thrown in there to fill out the group. Also ridiculous is you have Selma and Ling, who just wordlessly go along with the crowd in shaming and deserting Marge.
One good line/moment: Looking at old newspaper records on a monitor, Bart commands, “Zoom in and enhance!” Lisa shrugs, and simply pushes Bart’s head closer to the screen.

