Season 3: Episode 4. Original airdate: October 10, 1991.
“Bart the Murderer” would be an important episode in the show’s canon if it were only remembered for the introduction of Fat Tony. The crime boss of Springfield has become the archetypal gangster in pop culture, up there with Don Corleone, Tony Soprano, yada yada. Played to perfection by Joe Mantegna, Tony is a larger than life character that would fit in among the most powerful mobsters in fiction, but also feels right at home in Springfield. The show’s power in integrating so many different character types makes Springfield not only feel like an important city, but make it feel like every city, and certainly not just ones in Oregon.
While I find the introduction of Fat Tony to be an important aspect in the development of the show’s supporting cast, this episode does something even more interesting in its ability to toy with structure. It’s been using a pretty solid three-act structure up until this point, aside from those annual anthology episodes, but tonight’s episode plays with the confines of those three acts in a way that shows just how flexible the show can be. It’s equal parts a school story, a tale from the criminal underworld, and a courtroom drama—all within 22 minutes. This episode never loses its momentum, and it reveals just how comfortable the writers and producers were at this point.
The episode begins with Bart having a terrible, horrible, no good, very bad day. He doesn’t get the toy in his cereal, misses the bus, rips his pants, and worst of all, forgets his permission slip to visit the local chocolate factory. He’s instead given the “fun” opportunity to lick envelopes for Principal Skinner, continuing his streak of bad luck. After school, he trips on his skateboard, falls down some stairs, and finds himself cornered by the Legitimate Businessmen’s Social Club, aka the Springfield Mob.
Fat Tony and his cronies take a liking to Bart after he picks a winning horse, in a race filled with horses named after cartoon catchphrases (‘ain’t I a stinker?’, ‘That’s all folks’, and of course, ‘Eat my shorts’ and ‘Don’t have a cow’). He’s hired as a part-time lackey, mixing the gangsters Manhattans and cleaning up after them. What’s amazing is the similarity of this plot to Goodfellas, despite this episode being conceived BEFORE that movie came out. I’ll just chalk it up to a Simpsons miracle, because there’s no rational explanation of this beyond the genius of this creative team.
Bart eventually becomes such an important piece of the organization that Fat Tony is deeply troubled when he shows up late for work one afternoon. Bart tells him that Skinner kept him after school, and Tony ominously says he’ll take care of the principal, and his gang shows up at Skinner’s office in what seemed like the end for Seymour. The evidence against Tony mounts when Skinner goes missing, and Chief Wiggum shows up to bust the crew. Despite Tony’s talent at playing dumb (“what’s murder?”), everyone, including Bart, is dragged in for trial.
The trial is a pretty marvelous scene, and one of the best third acts I’ve seen the show do so far. From Lionel Hutz’s schtick to Tony’s declaration that Bart is the kingpin, it’s all solid gold. There are tons of tiny gags, like the newspaper cartoon of Bart as an octopus strangling Springfield, and it’s a nonstop barrage of jokes until Skinner himself bursts into the courtroom. Skinner’s story may be one of the greatest reversals in TV history, and it’s definitely one of his greatest moments as a character. He fell under a stack of newspapers after meeting with Tony, and was trapped for over a week, even though he screamed for help each time the police raided his house. His MacGyver escape involving a vacuum cleaner makes the story even more ludicrous, but it’s all somehow believable in the insane context this episode has developed.
Bart is proven innocent, and Tony and his gang live to scheme another day. They’ll be seen many more times (thank goodness), and this episode is a tremendous introduction to the seedy criminal underbelly of Springfield. The confidently loose structure of this one is something I hope to see a lot of in these coming seasons, and it’s proving how deft the writers were at their job by this point. Season 3 is the beginning of this group at their creative peaks, and it’s truly wonderful to behold.
Days of Homer 
Incredible episode
What’s an episode?
The later seasons will be much more challenging to watch than the golden years. I suggest you make a game out of it. See how many seconds you can watch without feeling depressed for all of humanity, and then try to break that record.