The montage near the end of the first act spoofs Bart's shots in the show's opening; additionally, Barney appears in place of the now-deceased Bleeding Gums Murphy, in the same place where Murphy would have appeared.
One of the candies that Bart eats is named Cop Killaz.
This episode reveals that Bart is allergic to cauliflower (adding to the other food allergies he has: shrimp, butterscotch, and imitation butterscotch).
In the Itchy & Scratchy cartoon, the medical questionnaire that Scratchy fills out asks "Have You Ever Been:" followed by a list of catastrophic events, all of which happened to Scratchy in previous Itchy & Scratchy episodes (see "Kitty-Kill Condition").
Bart is the second character to have a heart attack (as well as the first kid).
The distance from Spangler's compound to the Simpson house is inconsistent. Earlier in the episode it's only an hour's drive; later, as Homer and Tab are out on the highway, Tab wants to stop at a motel overnight. It could be that he's trying to hit on Homer.
When Dr. Hibbert shows Bart's radiograph, there's a switch under the image, but when Marge points Bart's liver, there's a plate in the switch's place. When Dr. Hibbert says to Bart follow a diet, the switch's again in its place.
The title of this episode is probably a spoof of the 1972 film The Heartbreak Kid starring Charles Grodin. It may also reference World Wrestling Entertainment (WWE) Superstar Shawn Michaels whose nickname is "The Heartbreak Kid."
The song Homer sings for change to the German students on vacation is "99 Luftballons" by Nena.
The song played during Bart's junkfood sequence is "Yummy yummy yummy" by The Ohio Express.
The line "raged against the machine" is a reference to the political rap-rock band Rage Against the Machine.
Bart opens a package of candy, throws it in the air, and lets it fall down onto and around him, echoing the scene where Andy stands in the rain after his escape.
Bart's candy-tossing scene could also be considered a reference to the scene in Pleasantville where David stands in the rain and transforms from black-and-white to color.
Homer says (regarding the milkshakes from the festival), "They're melting," in a style reminiscent of The Wicked Witch of the West in The Wizard of Oz.
This episode's storyline is likely a satire of the real-world problem of vending machines in schools (which was briefly mentioned in the 2004 Morgan Spurlock film Super Size Me). In fact, some states have made it illegal for public schools to sell junk food to students during school hours.