Jenny resembles Samantha Stankey from Bart's Friend Falls in Love. Ironically, the exact reverse of the episode's events seem to be the main plot line. Like in "Bart's Friend Falls in Love" when Bart tries to ruin Milhouse's romance with Samantha Stankey and in this episode Milhouse tries to ruin Bart's relationship with Jenny.
When the letters from the school sign above the front door, say "Springfield Elementary School", fell down, the N's and a broken M became Z's over Willy's head.
When Milhouse said "Hello Bart" it sounded like something Sideshow Bob would say.
When giving Lisa her pills, Homer says "Sounds like someone's having the case of a Monday", a reference to the movie Office Space.
When Lisa first takes the pills the Louis Armstrong song "What A Wonderful World" plays.
When Lisa is under the drug effect in her room, the song "Don't Worry Be Happy" by Bobby McFerrin plays.
When Bart drinks a squishee at the Kwik-E-Mart, Apu refers to the Shrek series.
When Lisa takes the pills, she says, "I'm going to Dizzyland," very loosely based on the Disneyland Resort.
Bart and Milhouse pulled the prank outside of school hours meaning that Milhouse couldn't be suspended. It would have to be during school hours if there are kids there and the school bell rings.
When Groundskeeper Willie is knocked unconscious, three Ns land next to him. However, there are only two Ns in "SPRINGFIELD ELEMENTARY SCHOOL". However, one of the "M" legs fell, making the M like an N