[[caption-width-right:320:The road trip of hell.]]

Homer and Grampa smuggle prescription drugs in from Canada after Mr. Burns announces that the town's new healthcare plan is cutting prescription medications.
!!This episode contains examples of:
* BitingTheHandHumor: Flanders says his home-brewed coffee is "hotter than a Fox News weather skank."
* CallBack: Homer is referred to as [[Recap/TheSimpsonsS5E15DeepSpaceHomer "Former US Astronaut"]] after being arrested by Canadian authorities.
* ChekhovsGun: The Plywood Pelican is introduced at the beginning of the episode at the museum and is ignored after Burns cuts the plant's healthcare plan. During the climax, Burns, Homer and Abe use it to smuggle medication.
* DoesThisRemindYouOfAnything: Ned and Apu argue in the back seats of the car about faith, with Homer desperately trying to get them to shut up, like a parent trying to control his unruly children.
* EvenEvilHasStandards: Burns might have selfishly cancelled his employees' health care but he still felt the need to warn a female coworker that her new boyfriend is a married man.
* EvilCounterpart: What Ned deems his Canadian counterpart to be after the latter offers him a joint (even though, in RealLife, having non-medicinal marijuana is illegal in Canada. However, unlike most U.S. states and a majority of places overseas, if you get busted on possession of marijuana charges in Canada, you are fined rather than getting jailtime for it).
--> '''Ned''': They warned me Satan would be attractive.
* ExactWords: At the end of the episode, Burns said he'll restore the plant's health care program to all his "full-time employees". Cut to the next scene with Homer informing Marge he's now a "freelance consultant".
* {{Jerkass}}: When the Plywood Pelican is about to fall, Mr. Burns not only takes a parachute for himself but also the other parachutes, leaving Homer and Abe with no choice but to crash land.
* MyCountryTisOfTheeThatISting: When a Canadian express his desire of seeing a mentally challenged man's execution and claims it doesn't happen in Canada, Homer shows surprise and says it happens a lot in the United States.
* NotHelpingYourCase: When the Canadian Border Patrol surrounds the car, Homer tries to tell them they were simple tourists...only for the drugs they were smuggling across the border to spill out his door.
* NotWhatItLooksLike: When the guys are trying to get out of Canada with the drugs, Apu takes a sip of Ned's coffee, causing him to start screaming, so Ned wraps a towel around his head to cool him off. When the car reaches the border, Apu looks like a free-thinking Muslim.
-->'''Border Guard''': Stop him! [[FelonyMisdemeanor He's expressing his faith, eh!]]
* OverlyLongGag: The drugs spilling out of the car.
* OverlyNarrowSuperlative: Bart tells Lisa that Mr. Burns is one of the nicest men he ever met. When Lisa asks how many men he knows, he says it's basically Burns and Homer.
* PetTheDog: After Smithers becomes seriously ill due to his actions, Burns vows to move heaven and earth to save him...if only because it's easier than teaching someone new his filing system.
* ShoutOut
** Mr. Burns' plane is called the "Plywood Pelican", a parody of Howard Hughes' "Spruce Goose" (which was also parodied on the season five episode "$pringfield: or, How I Learned to Stop Worrying and Love Legalized Gambling" during the subplot of Mr. Burns becoming more and more like Howard Hughes in his later years).
** The Canadian drugstore Homer and his friends go to is called "[[WesternAnimation/DudleyDoRight Dudley Do-Drugs]]".
** During Ned and Apu's argument over religion, Ned sarcastically quips "Why don't you just call out for ComicBook/{{Hawkman}}?" after Apu cries to Shiva for help.
** Mr. Burns' rush to get Smithers his medicine towards the end spoofs ''Disney/SnowWhiteAndTheSevenDwarfs'' and ''Disney/SleepingBeauty''.
** The title is a pun on ''Film/MidnightExpress''.
* TemptingFate: Homer reassures his father that they'll get to Springfield in the Plywood Pelican on a wing and a prayer. [[RuleOfFunny One of the wings snaps off]].
** The episode's Couch Gag sees the family sit on the couch normally, the theme music having suddenly stopped. Lisa turns to the viewer, and asks, "What? Can't we sit on the couch without something happening?" Cue Homer taking the sharp end of a spear to the chest. He says, "D'oh!"
* TrollingTranslator: The Mountie screws with his French translator.
-->'''Mountie:''' We've confiscated your car and its contents.
-->'''French Translator:''' ''Nous avons confisqué votre voiture et son contenu.''
-->'''Mountie:''' You may leave Canada, but never return.
-->'''French Translator:''' ''Vous pouvez quitter le Canada, mais ne retournez jamais.''
-->'''Mountie:''' I am a big fat French idiot.
-->'''French Translator:''' ''Je suis un grand gros'' - HEY!