When Mr. Largo say, "No, you regained consciousness. Alison got First Chair....and believe me, this is not a dream!", to which Lisa gives off a Big "WAAAH!".
Marge says that Homer lost 40 dollars, because he didn't go to work. If Homer works eight hours every day, it means, that he grosses five dollars every hour.
Principal Skinner's favorite Star Wars character is Chewbacca.
This is the first episode where Lisa runs against a girl equal or higher than her standards.
It was revealed in the commentary for the episode, that Sara is named after one of Mike Scully's daughters.
It's worth noting that Lisa confronts Marge about her not being transferred to the third grade, yet in the episode Bart vs. Lisa vs. the Third Grade she actually was transferred and found herself not ready for this step.
The scene where a federal agent confronts Milhouse at a dam is identical to a scene from the 1993 movie The Fugitive. The agent resembles Tommy Lee Jones' character and uses he signature line "I don't care."
Marge is seen reading (and fantasizing about) a romance novel titled Love in the Time of Scurvy, which is a reference to Love in the Time of Cholera by Gabriel García Márquez. The pirate in Marge's fantasy bears a resemblance to romance novel model Fabio Lanzoni.
Homer's "In America" speech while guarding his sugar pile comes from Scarface.
The company "Goldsboro's Honey" is a reference to easy listening performer Bobby Goldsboro, who had a #1 hit in 1968 with the song "Honey."
Lisa's nightmare features her playing in a band with famous backup artists: Art Garfunkel, John Oates and Jim Messina. The concert is sponsored by Avis, the number two rental car company whose famed slogan is "We Try Harder." The song "Born to Runner-Up" is a parody of "Born to Run" by Bruce Springsteen, who never topped the Billboard Hot 100 charts. Springsteen's highest charting song was 1984's "Dancing in the Dark," which topped out at number two.