[[caption-width-right:274: [[DoubleTake Wait, what?!]].]]
Episode - 8F03\\
First Aired - 10/10/1991
Bart's bad day at school turns good when he gets a job as a gofer for local mob boss, Fat Tony, but spending time with mafioso may be turning Bart into one of them — especially when news hits that Principal Skinner has gone missing.
!!This episode provides examples of:
* AdaptationalWimp: Fat Tony, as portrayed in ''Blood On the Blackboard'', is a NervousWreck who gets slapped and bossed around by the film's version of Bart Simpson. [[AdaptationalAttractiveness And he's much slimmer too]].
* AffablyEvil: Fat Tony and his gang.
* AmoralAttorney: The General Attorney asks Skinner's testimony about how he is not dead to be removed from record. It gets rejected.
* AsHimself: Creator/NeilPatrickHarris (playing "Bart"); Joe Mantegna (playing Fat Tony) [both on the show and in the made-for-TV [[ShowWithinAShow movie within a sitcom]] ''Blood on the Blackboard: The Bart Simpson Story''].
* BaitAndSwitch: When Bart first stumbles upon the hangout and Fat Tony asks him to pick a horse in the third race.
-->'''Bart:''' Eat my shorts.
-->'''Fat Tony:''' Eat My Shorts? Okay, let's see - wait a minute, you little punk!... Eat My Shorts is in the fifth race! I said the third race!
* BookDumb: Bart. After his dog eats his homework, it spits a part that has "9 X 9 = 100".
* BribeBackfire: Bart's attempt to bribe Principal Skinner resulted in a mid-episode chalkboard gag ("I will not bribe Principal Skinner").
* ButtMonkey: Bart. Plain and simple.
* TheCameo: Sideshow Bob appears in the same jail cell as Bart, lifting weights.
* DirtyCoward: The mob find it more efficient to frame Bart for Skinner's murder than simply deny a crime they didn't commit.
** It helps that, through this, they can set him up for every other crime they're responsible for.
* DisproportionateRetribution: The visiting Don gives Fat Tony the KissOfDeath because his Manhattan wasn't good.
* ADogAteMyHomework: Santa's Little Helper eats Bart's homework. Bart is surprised that dogs really do that kind of thing.
* EarlyInstallmentWeirdness: Sideshow Bob, with bulgy arms from weight-lifting, sharing a cell with Bart ''and NOT trying to kill him?!''
** Principal Skinner is shown living by himself, instead of with his [[MyBelovedSmother Beloved Smother.]]
* EasilyCondemned: Bart is very quickly set up for murdering Skinner with next to no evidence. There wasn't even evidence to prove that Skinner was dead in the first place. The judge justifies this with the track record given by everyone whose put up with him, including his father.
* EvenEvilHasStandards: When Bart and Sideshow Bob are stuck in the same jail cell together, the latter appears to give a DisapprovingLook to the former.
* TheFreelanceShameSquad: Lisa is quite smug towards the horrible turn of events Bart suffers.
* GetAholdOfYourselfMan: Willie slaps Ms. Krabappel when she breaks down over the inauguration of a fire hose dedicated to Skinner's memory.
* GutFeeling: Marge suspects correctly that Bart is hanging out with criminals, and also suspicious with the pizza truck that's been parked across the street for two weeks. Homer mostly ignores her concerns ("a job is a job"). Angry at his indifference, Marge demands that Homer check to see if she's right.
* HumiliationConga: Bart throughout the entire first act.
* JerkassBall: Lisa in the first act.
* KarmaHoudini: The mobsters setting up Bart as a fall guy weren't punished for what they've done to him. They agree with Bart's theory that crime doesn't pay... [[IgnoredEpiphany Before each driving off in their large limos]].
* KissOfDeath: One is given to Fat Tony when he serves the Mafia boss a "flat, flavorless Manhattan" (due to Legs making it instead of the usual bartender, Bart).
* LegitimateBusinessmensSocialClub: This episode marks the first appearance of the TropeNamer.
* MacGyvering: Skinner escaped from his garage trap by building a rocket with baking soda and lemon juice.
* NeverFoundTheBody: And yet, everyone was willing to believe a ten-year-old would kill Principal Skinner. And as it turns out, the police didn't even look too hard.
-->'''Skinner:''' ''(in the basement)'' I'M IN HEREEEEEE!\\
'''Wiggum:''' Well, let's go.\\
'''Eddie:''' Okay, Chief.
* NotMyLuckyDay: Bart suffers a hefty HumiliationConga before coming face to face with the mafia.
** Bart when Santa's Little Helper eats his homework. He then remarks that he didn't know dogs really did that.
** Bart lets out a horrified scream when he realises he left his permission slip for the chocolate factory field trip at home.
** Bart again when he finds himself with several gun barrels in his face held by the Mafia when he first encounters them. "Uh-oh", indeed.
* TheOldestProfession: Supposedly, one of the rackets Bart was involved in as head of the Mafia.
* PoliceAreUseless: They searched Skinner's home, but all they did was dig around his bedroom. They never checked the basement where Skinner was trapped and somehow never heard his loud cries for help.
* ScrewTheMoneyIHaveRules: Skinner wouldn't accept bribes.
* SmokingGun: Skinner suddenly enters the courtroom when the judge is about to declare Bart guilty of his murder.
* SpecialGuest: Creator/PhilHartman as Lionel Hutz and Troy [=McClure=]; Joe Mantegna as Fat Tony
** After almost being convicted for a crime that didn't even happen, Bart said he learned crime didn't pay. Fat Tony says he agrees... only to leave the courthouse in a limousine, which is followed by limousines belonging to Legs and Louie.
** Skinner was trapped in his basement because a large pile of newspapers fell on top of him and kept him trapped. He later says, "Let this be a lesson to recycle frequently."
** After Homer finds hundreds of cigarette cartons in Bart's room, he orders Bart to smoke them all all to teach him a lesson. However, once Fat Tony's delivery guy comes to pick them up, Homer apologizes for doubting Bart's explanation.
* SpyShip: A pizza truck's been parked outside of the Simpson house for two weeks. When Marge asks, "How long does it take to deliver a pizza?", the agents inside remark that their cover's blown and pull away, only to be immediately replaced by a "'''F'''lowers '''B'''y '''I'''rene" truck.
--> '''Fat Tony''': You Skinner?\\
'''Skinner''': ''(angrily)'' I'm ''Principal'' Skinner, yes!
* TookALevelInJerkass: Lisa has a moment of this. Bart can be a pain sometimes, but he hadn't done anything to ''deserve'' missing the field trip of his dreams.
** Same goes for Homer while in court, in the third act. ''He was about to accuse his son of being the Springfield Mafia's leader.'' Also counts as a TookALevelInDumbass moment (''even for Homer'').
* VeryLooselyBasedOnATrueStory: In-universe example. ''Blood On The Blackboard: The Bart Simpson Story'' portrays Bart as a hardened mobster who genuinely attempts to murder Skinner, despite the movie being made after he was proven innocent. According to Marge, the changes were actually still subtle enough they didn't have to pay them royalties.
* WhatTheHellTownspeople: The townsfolk took idiocy to a new level by believing a ten-year-old would head the local Mafia. Then again, given that this is Bart we're talking about, it might not be that hard to believe for them.
-->'''Lionel Hutz:''' Mr. Simpson, you've been the boy's father for ten years. Do you really think he could be the leader of a murderous criminal syndicate?\\
'''Homer:''' Well, not the leader, I mean... ''[looks over at Bart, then cries]'' Oh, it's true, it's true! All the pieces fit! ''[bawls]''