Original air date: 2/17/2002 (produced in 2001)
Production code: DABF-06
Bart falls in love with Rainier Wolfcastle's daughter and the family goes to Canada. Meanwhile, Principal Skinner becomes a stand-up comic.
Tropes:
- Artistic License – Medicine: Homer assumes that due to Canada’s “free healthcare”, he can all-but-deliberately injure himself and not be on the hook for any medical bills. This is definitely not true, as not only is Medicare in Canada administered provincally (though partially federally funded), like in other provinces, the Ontario Health Insurance Plan only covers Canadian citizens and permanent residents. Since Homer is unlikely to carry travel insurance, he will have to pay for whatever medical care he would need. Of course, this is Homer we’re talking about, and on the upside, depending on the service needed, the amount he’d be charged would still be noticeably lower than in a lot of regions in the U.S.
- Big "NO!": The police officer from the beginning of the episode lets one out when he find the Olympic torch extinguished after crashing the helicopter.
- Bigfoot, Sasquatch, and Yeti: A sasquatch can be seen getting off the bus the Simpsons are on when they arrive at Canada.
- Body Horror: Lenny has been using Wolfcastle's products backwards and has a muscular back that sports its own chest and abs.
- Did Not Get the Girl: In the end Bart begs Greta to take him back she gives him a flat no, then breaks up with Milhouse.
- Dinner And A Break Up: Rainer Wolfcastle's daughter Greta, develops a crush on Bart, to which he’s oblivious. Lisa calls him out on leaving her hanging and how he needs to do something before she gets hurt. So Bart handles it by taking her to the ice cream parlor and breaks up with her, sending her to tears.Squeaky Voiced Teen: Don't worry. We get a lot of that here. (Cut to Lou telling a grieving Chief Wiggum that he’s leaving the force)
- Does This Remind You of Anything?: When an excited Milhouse takes a running jump into Greta's pool, Bart knowingly chuckles "He'll sleep tonight" like the parent of a hyperactive toddler.
- Exact Words: When the Simpsons went to Canada, Homer said they'd go "first class". Cut to them on a first class bus.
- Gone Horribly Right: Homer tries to humiliate Flanders by writing his name on a sheet of paper. Ned ends up winning $100, which he donates to an orphanage.
- Green-Eyed Epiphany: Bart is pretty much only interested in Greta because she pulled Operation: Jealousy with Milhouse after he "dumped" her.
- In-Character Commentaries: Seen In-Universe with the "Itchy & Scratchy" DVD commentary. Of course, this being Itchy and Scratchy, Itchy ends up killing Scratchy during the commentary.
- Logo Joke: The "shh" in the Gracie Films logo is replaced with Milhouse's "wazuuup?".
- Made of Plasticine: While filming Undercover Nerd, Wolfcastle picks up one bully and throws him THROUGH another bully, leaving the former stuck halfway through the latter.
- The Mountains of Illinois: Toronto is shown as mountainous and countryside can be seen right outside the CN tower, where in real life Greater Toronto is flat and has extensive urban sprawl.
- Noodle Incident: Apparently, the family once went on a trip to Europe to retrieve Lisa's lost balloon.
- Oblivious to Love: Greta develops a crush on Bart, who doesn't realize what his relationship with Greta means until Lisa scolds him for standing her up. We then see a flashback to Bart and Greta playing a game of Scrabble. Greta has spelled out numerous words that have to do with romance. Bart spells out the word "oblivious".
- Old Money: Some prep school students pick on Wolfcastle's daughter because she's New Money.
- Operation: Jealousy: Bart claims that Greta's only dating Milhouse for this reason—Milhouse acknowledges that Bart's right but is perfectly fine with it, saying his therapist told him that such a situation was the best he could ever hope for.
- Paper-Thin Disguise: Ranier Wolfcastle playing a nerd named Melvin Eugene Punymeyer in his movie Undercover Nerd.
- Pre-Asskicking One-Liner: Wolfcastle quips "The geek shall inherit the Earth!" before going Bully Hunter in Undercover Nerd.
- Pun-Based Title: On "the heart wants what it wants".
- Sure, Let's Go with That: Greta thinks Bart's joking when he says his mattress is filled with hay and he decides to let her think she got it right.
- Take That!:
- When Homer takes the Olympic torch, he chastises the practice of the games preempting his favorite programs.
- When Skinner starts stealing from the prep school, he responds to Lisa’s chastisement with “Welcome to Dick Cheney’s America”.
- While Bart and Greta are watching an Itchy & Scratchy cartoon with the
DVD Commentary on and both of them discuss the long, gruelling hours, Itchy then quips "You can never get enough takes with Steven Soderbergh!"
- Unrequited Love Switcheroo: Bart has no interest in Greta and dumps her the moment he realizes she thinks they're dating. She then moves on to Milhouse, and suddenly Bart wants her more than anything. Lisa even spells out the fact that he only wants her because he can't have her, but Bart still doesn't get it.
