1.During the casting process, the film makers went to different New England private schools, mostly in Massachusetts, looking for a student to play Max Fisher.
2.The movie's line "Yeah, I was in the shit." was voted as the #56 of "The 100 Greatest Movie Lines" by Premiere in 2007.
3.When Ms. Cross and Max feed the fish and talk about deaths of loved ones, Jason Schwartzman (Max) had to stand on boxes so he could be the same height as Olivia Williams (Ms. Cross).
4.The pictures of Ms. Cross' dead husband in her bedroom are pictures of co-writer Owen Wilson.
5.The Bentley used in the film was used in exchange for the owner's daughter to appear in the film.
6.When Bill Murray first read the script, he thought it was so fantastic that he said he wanted to do it so badly he would do it for free.
7.Film debut of Alexis Bledel who can be seen sitting on the right in the Grover Cleveland classroom just before Max (Jason Schwartzman) makes his speech.
8.In a shot of Max's petition to save Latin, the names of Jason Schwartzman's band mates from Phantom Planet, as well as the name of the band's manager (Dan Field) can be seen in the middle of the left column.
9.Bill Murray's character wears the same suit throughout the entire film. He just changes his shirt and tie, which are always the same color as each other.
10.Bill Murray genuinely found the Keith McCawley and Ronnie McCawley who play his sons and were very much like their screen characters, annoying, and many of the scenes where he lashes out at them and insults them were improvised.
11.A shot of Max Fischer sitting on a go-kart wearing a pair of goggles is a recreation of a photograph taken in 1909 by French photographer Jacques Henri Lartigue, a child prodigy who started taking photographs at the age of 6.
12.In the geometry class Max dreams about during the school chapel/assembly, he solves a problem on the board - this problem is to derive the area of an ellipse by integrating its equation.
13.Wes Anderson had originally envisioned Noah Taylor for the role of Max Fischer.
14.The speech about privilege that Bill Murray gives at the beginning of the film was inspired by an actual speech once given by Robert Wilson, father of Andrew Wilson, Luke Wilson and Owen Wilson.
15.Like Max Fischer, Owen Wilson was expelled from his prep school in the tenth grade.
16.1,800 teenagers were auditioned from the United States, Canada and England for the part of Max Fischer.
17.Jason Schwartzman came to his audition wearing a prep-school blazer which sported a Rushmore patch he had made himself.
18.Brian Cox was cast on the strength of his performance in Manhunter.
19.The book Max is reading at the beginning of the movie is "Diving for Sunken Treasure" by Jacques-Yves Cousteau who was the main inspiration for Wes Anderson's later film, The Life Aquatic with Steve Zissou
20.According to Bill Murray, he disliked Jason Schwartzman's personality during their first meeting. But he eventually warmed up to him while they worked together.