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:
- Biting-the-Hand Humor: Flanders says his home-brewed coffee is "hotter than a Fox News weather skank."
- Call Back: Homer is referred to as "Former US Astronaut" after being arrested by Canadian authorities.
- Does This Remind You of Anything?: 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.
- Even Evil Has Standards: 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.
- Evil Counterpart: What Ned deems his Canadian counterpart to be after the latter offers him a joint (even though, in Real Life, 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 don't get jailtime for it).Ned: They warned me Satan would be attractive.
- Exact Words: 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".
- Mistaken for Terrorist: Apu when the guys try go get out of Canada with the drugs. He puts a towel around his head (resembling a turban) and spills hot coffee on his lap, making him let out a scream that sounds like a battle cry.
- My Country Tis of Thee That I Sting: 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.
- Overly Narrow Superlative: 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.
- 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 "Dudley Do-Drugs".
- During Ned and Apu's argument over religion, Ned sarcastically quips "Why don't you just call out for Hawkman?" after Apu cries to Shiva for help.
- Mr. Burns' rush to get Smithers his medicine towards the end spoofs Snow White and the Seven Dwarfs and Sleeping Beauty.
- The title is a pun on Midnight Express.
- Tempting Fate: Homer reassures his father that they'll get to Springfield in the Plywood Pelican on a wing and a prayer. 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!"
- Trolling Translator: 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!