Actor Allusion: Five minutes into the movie we see Matthew Broderick's Mr. McAllister throwing questions to the class and asking "anybody?" (He also narrates quite a lot, and is shown taking showers in a very similar manner; all that's needed is a chorus of "Danke Schön.") Hell, Matthew Broderick starring in any high school movie after having established his career playing Ferris Bueller.
Dawson Casting: Resse Witherspoon and Chris Klein were 23 and 20 respectively when they starred in this film. Averted with most of the extras and minor student roles as it was filmed on location at a real high school.
Disabled Character, Disabled Actor: A wheelchair-bound teenager plays the candidate who runs unopposed for student council Vice President, either because no one else cares about that position or no one has the heart to run against a disabled kid. On IMDB this is his only film credit, presumably he was a real high school student like all the extras in this film were.
I Am Not Spock: This briefly happened with Reese Witherspoon, whose performance was so convincing that she had trouble getting work for a few years, since producers thought that her performance was indicative of her Real Life personality. She's since broken out of this typecasting.
Reese Witherspoon originally wanted to play Tammy.
The director wanted more than anything else to edit the climax of the film In the Style of... the final showdown from The Good The Bad And The Ugly. His editor, however, was willing to sacrifice part of his paycheck so that he wouldn't.