Homer (like practically every Springfielder who isn't a Flanders) waits until the last minute to file his tax return, and the IRS has jailtime in store for Homer -- unless Homer plays spy to retrieve a trillion-dollar bill that Mr. Burns was supposed to deliver to post-UsefulNotes/WorldWarII Europe to pay for reconstruction and stimulate the economy.

* AbusiveAdvertising: The Duff ad in Cuba with Che Guevara has the slogan "El Duff-o o muerte (or death)". Considering that it's on a communist nation that executes prisoners...
* AllOfThem: The reasons for visiting Cuba are: business/pleasure; smuggle cigars; assassinate Castro. Homer checks all of them.
* BadLiar: Want an idea of how poorly Homer did his taxes?
-->'''Homer:''' Okay, Marge, if anyone asks you require 24-hour nursing care, Lisa's a clergyman, Maggie is seven people, and Bart was wounded in [[UsefulNotes/TheVietnamWar Vietnam]]!
* BoxedCrook: Homer agrees to work as an IRS snitch to avoid going to jail.
* CallBack: When Kent Brockman asks Krusty the Clown why he waited till the last minute to file his taxes, he says [[SarcasmMode "Because I'm an idiot. Happy?"]] Evidently, he hasn't gotten over his brush with the IRS in "Bart the Fink".
* CrazyPrepared: Ned always files his tax returns ''every'' New Years.
* ChekhovsGun: The plane Burns is seen using to "take" the dollar bill to France turns out to still be in his possession on the third act, and it's used to go to Cuba.
* TheDeadRiseToAdvertise: A billboard of Che Guevera is seen advertising Duff Beer.
* DiscoDan: Mr. Burns' out-of-touch-with-the-times tendencies are in full display here. He thinks Homer is a reporter for ''Collier's'', which had ceased publication in 1957 (although it was briefly revived in 2012), and while in Cuba, was shocked to learn that [[UsefulNotes/FulgencioBatista Batista]] was no longer in charge. He also identifies a taxi as "the new Packard they've been talking about."
* DoesThisMakeMeLookFat: Homer asks this about the wire he has to wear under his shirt.
-->'''Lisa:''' No, it makes you look like a tool of government oppression.\\
'''Homer:''' But not fat.
* DudeWheresMyRespect: Smithers is upset when Mr. Burns doesn't appreciate the dinner he prepared, saying "Sometimes, I don't know why I bother..."
* ExactWords: Doubles with PoliceAreUseless. When Homer, Smithers and Burns escape from Burns' mansion, Chief Wiggum receives a radio message to look out for Burns' maroon-coloured car. When it drives by, Wiggum notes the car is more of a burgundy and does nothing.
* FrenchJerk: Apparently, this trait started because Burns stole the trillion dollar bill meant for Europe.
* HistoricalInJoke: Mr. Burns has the suit Creator/CharlieChaplin was buried in, which suggests that Burns was the one who stole Chaplin's coffin in 1978, a few months after Chaplin's death and funeral.
* HorribleJudgeOfCharacter:
** Everyone who expected Mr. Burns to be the most reliable person to deliver the trillion-dollar-bill just because he's America's richest person.
** Mr. Burns simply gives the dollar bill to Fidel Castro, who is an extremely corrupt man. When Mr. Burns asks him to give it back, the president just asks what, taking the money away and putting Mr. Burns, Smithers, and Homer on a meager rack in the middle of the ocean.
* InsaneTrollLogic: After Marge points out how Homer is lying on his taxes (as he rushes to complete them last minute), he immediately covers his ears.
-->'''Homer''': Shut up, shut up! If I don't hear you, it's not illegal!
* IntimidatingRevenueService: Homer is forced by the IRS to become a spy for them or face criminal charges for his badly-made tax forms (ironically he may have prevented this by just not bundling all of the forms together into the shape of a football).
* {{Irony}}: Burns was chosen to deliver the dollar bill because he was one of the most trusted men in America to do the job. Not only does he ''not'' do that, believing it's his patriotic duty to perform said theft, but other episodes (NegativeContinuity aside) have mentioned that he was a '''Nazi collaborator'''.
* MixedMetaphor: While reporting the midnight rush for mailing taxes, Kent Brockman says "It's literally the eleventh hour: 10 PM!".
* OhCrap[=/=]ThisIsGonnaSuck: The [[http://www.springfieldspringfield.co.uk/view_image.php?tv-show=simpsons&image=s09e20_196 look on Homer and Smithers' faces]] after they remind Mr. Burns that he's flying the plane... and he's about to attempt a landing.
* OutOfCharacterMoment: When the family is being asked by government agents what would Homer do with the ZillionDollarBill he's been accused of stealing, Marge says that the money should go to the kids' college fund... only for ''Lisa'' to reply "Who needs college? Let's buy dune buggies!" '''''Huh?''''' This coming from the girl who, after helping put Mr. Burns back on his feet, refused her rightful million dollar advisor fee out of moral disapprobation for how he did it.
* ThePasswordIsAlwaysSwordfish: The codeword to activate the secret film strip about the trillion dollar bill in the mall's photo booth is "cheese". Apu inadvertently activates it right after Homer and the IRS agent leave.
* RidiculousProcrastinator: Inverted. Ned Flanders begins preparing his taxes ''after midnight on New Year's Day''. Played straight with just about everyone else in Springfield, who only start filing their taxes at the last minute, and the reason Homer's whole dilemma occurs is because he was the one who waited the most out of the whole city (rushingly bundling all of his badly-filled forms into a bundle shaped like a football (which made it roll into the audit bin at the IRS) and actually having to toss it into the outgoing mail pile through the closing office's doors).
* ScrewTheRulesIHaveMoney: How Mr. Burns intends to avoid punishment.
-->'''Mr. Burns:''' And if it's a crime to bribe a jury, then so help me, I'll soon be guilty of that!\\
'''Homer:''' ''(stands up to salute)'' God bless America!
* SkewedPriorities: Homer has just a few minutes to file his tax return and won't stop for anything... other than a [[BigEater hot dog]].
* SuicidePill: Homer almost takes his when he thinks Mr. Burns is onto him. He considers taking it again when Burns tells him they're going to walk.
* TaxmanTakesTheWinnings: There's one scene with the Sea Captain taking a necklace from a treasure chest and placing it inside an envelope while waiting for his turn to mail his tax forms. He's wondering why he bothered to pillage that treasure.
* TemptingFate: While showing the big lines of people who waited until the last day to file their tax returns, Kent Brockman isn't worried because he'd previously sent his tax data to an accountant. Said accountant then shows up and is just as worried as everybody else.
* ThisPageWillSelfDestruct: The film the IRS shows to Homer ends with "This film will self destruct... if improperly stored."
* VacationEpisode: Homer, Smithers and Burns travel to Cuba in the final act.
* WhenTheClockStrikesTwelve: The post office closes at midnight and everyone who waited until the last day to file their tax return must do so until then.
* ZillionDollarBill: The trillion dollar bill meant for the reconstruction of Europe after WWII, but pocketed by Mr. Burns.