According to a sign Skinner passes on the edge of town, Springfield is 2,653 miles from Orlando. Estimating that Springfield is located in either California, Oregon, Washington or Idaho.
The original title for this episode is "Love and Marking".
A member of the Teacher of the Year foundation looks surprisingly like Skinner but with slightly darker skin, black hair, and a gray suit.
One of the teacher's tapes that the Teacher of the Year board is a reference to John Keating, Robin Williams' character in the film Dead Poets Society (which is mentioned negatively by one of the board members).
Keatin is voiced by Dan Castellaneta, who would later voice The Genie, another one of Robin Williams' characters.
A member of the Bully of the Year foundation looks surprisingly like Superintendent Chalmers, only with a bigger nose.
Homer first mistakes Little Richard for Prince (when he asks him to play "Purple Rain") for Michael Jackson. In Stark Raving Dad, he met a mental patient who claimed to be Michael Jackson.
Greta Wolfcastle makes a cameo in this episode.
The days of the week on Bart's calendar match up with that of January 2003. This episode actually did air in that month.
Bart asks if World War I was the war with Hitler in it. Although Hitler is generally associated with the Second World War, he DID fight in World War I, so Bart is actually not wrong here.
At the point in the episode where Edna confronts Principal Skinner in front of the hotel about his mother, Principal Skinner informs her that he was in fact in his mothers womb for over nine months. However, it was revealed in "The Principal and the Pauper", that in fact Principal Skinner is a fraud that has been impersonating the real Principal. In that episode, they meet and eventually the town decides they like fake Skinner better than real Skinner, though considering the fan backlash of "The Principal and the Pauper" over screwing with Principal Skinner's backstory, this could be the writers' way of telling viewers that all the events that happened in "The Principal and the Pauper" never happened and that Skinner is indeed the biological son of Agnes.
The song "Happy Together" by the Turtles, which plays in Eastern Airlines' "World of Tomorrow" presentation from 1965, was actually released in 1967.
The title of the episode is a parody of Special Ed, abbreviation of Special Education.
This episode features a parody of the EPCOT Center. A sign outside the park reads "When Every Other Place is Booked," and Homer moans that EFCOT is "even boring to fly over!"
The references to EPCOT Center being different from Walt Disney World is confusing, since EPCOT is indeed one of the four Disney theme parks in Orlando that makes up Walt Disney World. Homer's reference to Disney World and the location to which he escapes at the end is most likely a reference to the Magic Kingdom park. Alternatively, it may be an indication that EFCOT is a distinct entity from Walt Disney World's Epcot.
The "Ride Of Broken Dreams" is a mockery of the Enron scandal. The ride goes up for quite a distance, then suddenly drops steeply and levels out for a while and then drops down into a poor house shed.
The World of Tomorrow attraction has some basis in the former Magic Kingdom attraction If You Had Wings, which was sponsored by Eastern Airlines
The building where the award ceremony is held is an exact likeness of Epcot's Horizons.
The Electric Car of the Future, a parody of World of Motion, which was sponsored by General Motors (its replacement, Test Track, still is sponsored by General Motors).
The nighttime fireworks/laser display being watched by Homer and Marge is a parody of Epcot's Illuminations show, taking place in a facsimile of Epcot's World Showcase.
The "World of Tomorrow" ride parodies the fact that most of Epcot's attractions were sponsored by huge corporations (General Electric, AT&T, Exxon, United Technologies) that used their attractions to offer a very clean version of themselves and how they were bringing the future to the American public.
Julio Estudiante, the teacher who was awarded the title "Teacher of the Year" is a parody of Jaime Escalante and the 1988 film Stand and Deliver, where Escalante indeed taught inner city school students that differential equations were more powerful than bullets.
When Homer and Bart ride the electric car, the gay robots say "One of us! One of us!" This is homage to the classic line from the 1932 film Freaks. The ride, sponsored by "gas producers of America" exhibits a veiled parody of smear campaigns and conspiracies by oil companies (such as the Streetcar Scandal) to squash alternative transportation (such as mass transit and electric cars) and expand the use of gasoline-powered automobiles.
The scene where Skinner drives Willies car and he appears on a screen, the music that plays is similar to James Bond.
Edna mentions that she accidentally showed the "R-rated version of Romeo and Juliet", which is the 1968 film adaptation.
The opening music to the documentary on holes is the beginning of "Fragile" by Sting. This is a reference to the IMAX documentary The Living Sea, whose soundtrack featured the same song.
EPCOT had an attraction called The Living Seas from 1986 until 2006.
When Lisa mocks Bart for befriending Edna, she quotes "put mothballs in the beef stew", a line from the Simpsons' hit single "Do the Bartman".
When Skinner asks Bart to stop Edna from winning the award, Bart is playing "Halloween Hit and Run", which is a reference to "Simpsons Hit and Run". Skinner also mutters that "he can't believe they got away with this", which may be referring to the extreme amount of violence the game has.
The Electric Car of the Future's voice resembles that of Hanna-Barbera cartoon character Hardy Har Har.
Eastern Airlines was a real airline that ceased operations in 1991, and appears here in the joke that they would be predicted to remain afloat as did many companies in the 60s.