The previous episode found a vein of both comedy and pathos in the limits of Homer’s assholishness; “Bart The Murderer” finds it in Lisa Bart. As he’ll put it a few seasons later, Bart doesn’t want to be a criminal, he wants to be a petty thug, and this episode first shows that by exposing him to some honest-to-god criminals with our first appearance of Fat Tony and the mob. As usual, the show takes the long way around to this idea, though in this case there is an emotional continuity, in that act one consists of Bart’s shittest day ever. Again, the show’s ability to take a child’s point of view pays off enormously, as it delivers a cartoony exaggeration of things that happen all the time – just today, I rugged up for wet weather only to have it immediately stop raining when I stepped out, so I was boiling all day – until he’s left miserable and alone licking stamps all day while everyone else is out eating chocolate.
It’s in this mood that he stumbles into the legitimate business club of Fat Tony, and after some initial complications with guns, Fat Tony mistakes Bart’s catchphrases for tips on the horse races (hilariously, because all the horses have cartoon catchphrases), and then orders him to make a Manhattan; Bart finds he’s actually pretty good at it, and soon he’s in Tony’s employ and in his natural element; Bart’s always had both a grifter mindset and a tendency towards classiness, and the mixture of extremely good tips and the cool environment are enough to make him happy to do the menial tasks he gets.
Where this twists is when Fat Tony steals a truck full of cigarettes and stashes them in Bart’s room. What makes this plot great is that it happens entirely off-screen – first, Wiggum comes over and accuses Fat Tony, then there’s a scene of Homer discovering Bart’s room full of cigarette packets (assuming he’s taking up smoking and threatening to make him smoke every single one), then there’s a news story on the stolen cigarettes; this all allows the show to make a wide variety of jokes, from Wiggum’s stupidity to Homer’s stupidity to satire of cigarette companies, without sacrificing story momentum orunpredictability.
Bart, worried he’s working for a crook, asks Fat Tony what’s up, and Tony convinces him to look the other way by riffing on the “is it right to steal bread to feed your starving family” concept, then turns Homer by inviting him over to play poker and deliberately losing to him (appealing to Homer’s greed and ego usually being the right way to win him over). Bart, now fully sold on the gangster lifestyle, starts trying to bring its tactics onto the schoolyard; I wish the episode had gone more into that because I always get a kick out of Bart acting like an adult, but we just get one scene of Bart trying to bribe Skinner before being sent to detention.
What seems like a quick gag turns into a plot point, as this causes Bart to be late for work, which means he can’t calm one of Tony’s associates down with one of his Manhattans; when Bart finally gets in, he complains about Skinner holding him back, and Fat Tony decides to pay Skinner a visit. The next day, Skinner is missing (cue the children: “YAAAAAAY!”), and Bart is terrified that Tony had him whacked and wracked with guilt. The montage of Skinner missing is great – it definitely has one of the best “psychic helping the police” gags I’ve ever seen, and it builds into a spectacular dream sequence where Bart imagines the dead Skinner coming for him in a beautiful blue-and-black nightmare.
The mob is eventually arrested for Skinner’s murder, and all of them pin everything on Bart; even Homer crumbles and accuses Bart of everything. But, right when the judge is about to declare Bart guilty, Skinner throws the court’s doors open, revealing himself as not just alive, but the MVP of the episode. We’ve discussed Skinner’s squarishness before, and we saw hints of that back in ”Principal Charming”, but it fully blooms in this episode. In the first act, he was genuinely enthused by the prospect of licking envelopes all day, and encouraged Bart to make a game out of it; here, he reveals that Fat Tony simply tried to reason with him, and the reason he was missing was because he trapped himself under a pile of newspapers, where he couldn’t be heard by searching police. His solution to his problem is using fourth-grade science to MacGuyver his way out; his explanation of all this is incredibly dorky – “I survived by subsisting on Mother’s delicious preserves,” and “let this be a lesson to recycle frequently!”.
The ending of this episode is not just typical for The Simpsons, it’s almost a collation of Simpsons ending tropes at this point – the restoration of status quo as Bart is free to go, the subversive joke as Bart observes crime doesn’t pay, only for Fat Tony to drive away in one of his many limos, a TV satire as the Simpsons watch an incredibly inaccurate TV movie based on the events of the episode (with Neil Patrick Harris playing himself playing Bart), and a meta joke as Homer complains about Hollywood executives, only for the executive producer credit of the show to pop up.
Chalkboard Gag: High explosives and school don’t mix.
Couch Gag: The family forms a human centipede pyramid.
The episode was written by John Swartzwelder and directed by Rich Moore, and you can see Moore’s fingerprints all over the dream sequence. It contains references to Goodfellas(which was released during production) and The Godfather. “One Fine Day” by The Chiffons and “Witchcraft” by Frank Sinatra both appear in the episode.
First Appearances: Fat Tony, Legs, Louie.
Biggest Laugh: “I don’t have an appointment with any large men.”