Zach doesn't want to go to his Dad's alma mater, Dartmouth. His dad is played by Tim Matheson who starred in Animal House (1978), which was partly inspired by the time of of the film's writers spent at Dartmouth. At the end of "Animal House", Matheson is said to move to California and become a doctor . . . which he is in this film.
The character "Brock Hudson" was actually named after a real-life student of the same name at St. John's School in Houston, Texas, the same school where Rushmore (1998) was filmed. Screenwriter R. Lee Fleming Jr. went to this school, along with Wes Anderson (director of "Rushmore") and Will Wallace, where the phrase "what kind of name is Brock Hudson?" (used twice in this movie) was commonly heard.
Freddie Prinze Jr. and Matthew Lillard appeared together again in the Scooby-Doo movies, as Fred and Shaggy. Those movies also featured Sarah Michelle Gellar (mentioned in another trivia item here) as Daphne.
In a 2013 interview, M. Night Shyamalan claimed to have ghostwritten the script. Fleming has denied this. On the Blu-ray commentary for the film, director Robert Iscove confirms that Shyamalan was brought in after pre-production began as a contributor to the script. After his story points were added, the final rewrite was then handed back to Fleming so that he could lend the story his unique voice in writing for teenage characters.
Dulé Hill stars as a main characters on the tv series Psych (2006), while Rachael Leigh Cook, Freddie Prinze Jr., Elden Henson, Tamara Mello and Carlos Jacott, all make guest appearances at separate times during the series, respectively.
The film contains several hidden references to the pop group Hanson, aside from the photograph during Taylor's campaign. The two main characters are named Taylor and Zac - two of the members of Hanson. Mackenzie, and Jesse - two minor characters, were younger members of the Hanson family.
Elden Henson (Jesse) and Anna Paquin (Mackenzie) would go on to star in productions from Marvel Comics. Henson in Netflix's Daredevil and Paquin in the X-Men franchise. On top of that, Henson's Daredevil co-star Daborah Ann Woll co-starred with Paquin on HBO's True Blood.
The trivia item below may give away important plot points.
At the end of the movie, Freddie Prinze, Jr. is forced by Paul Walker to attend his graduation ceremony naked. In Joy Ride (2001), Paul Walker is forced to walk naked through a diner. However, Paul Walker was totally naked when he filmed his nude scene in Joy Ride (2001). Freddie Prinze, Jr. was not really naked in the nude scene in this movie.