Most every one in Springfield believes Bart Simpson will grow up bad.
But somehow, Bart manages to join the mafia before his eleventh birthday.
Yes, after an awful day of Alexander-level awfulness, a day where Bart misses the bus, has to travel through the rain, gets to school late, has his dog eat his homework, and forgets his permission slip for the field trip to the chocolate factory, Bart accidentally lands outside the Legitimate Businessman’s Club, headquarters for local mob boss Fat Tony.
Fortunately for Bart, his ability to pick horses and mix drinks manages to get him a job and not a shallow grave. Bart gets a ton of clues that these guys are up to no good, but he chooses to ignore them while earning very large tips and fine suits. Heck, the one time he outright asks them if they’re crooks, Fat Tony manages to ask a bunch of questions to throw Bart off-track.
Fat Tony is a comic delight. As voiced for the first of many times by actor Joe Mantegna, Fat Tony takes playing dumb to a new level (“What’s a truck?”). Granted, that level of stupidity might actually work on Chief Wiggum, but it does get the whole gang plus Bart hauled away when it looks like Principal Skinner has been murdered (“What a moider?”).
And then the gang’s legal defense is to pin the blame on Bart. All of it. Somehow, Bart becomes the mob boss and even Homer can’t say it couldn’t possibly be true. The only thing that keeps Bart free, after sharing a cell with a much more muscular-looking Sideshow Bob, is that Skinner isn’t dead. He was stuck in his garage under a pile of old newspapers, and Wiggum’s effectiveness in investigation means the cops never looked in there the many times they searched Skinner’s house.
I will say there’s a great Simpsons dream sequence in there, where Bart imagines he’s responsible for Skinner’s death and gets sent to the Death House. The protestors outside include Homer chanting, “Kill my boy!”
Too bad we couldn’t see more of that TV movie at the end of the episode, where Neil Patrick Harris plays Bart and Joe Mantegna plays Fat Tony. And then the serpent ate its own tail…