1. Alexis Bledel is in the film.
Before she starred as Rory Gilmore on Gilmore Girls, actress Alexis Bledel was an uncredited extra—she played a Grover Cleveland High School student—in Rushmore. You can see her in the background in various scenes, including dancing with the character Magnus Buchan (Stephen McCole) at the end of the film.
2. Rushmore Academy was the director's Alma Mater.
Director Wes Anderson sent location scouts across the United States and Canada to find the perfect high school to shoot the movie. He was having a tough time trying to find the school, until his mother sent him a picture of his old high school in Houston, Texas: St. John's School. Anderson thought it was the perfect location to make the movie.
3. Film critic Pauline Kael had a private screening.
Pauline Kael’s film criticism was a heavy influence on Wes Anderson’s view of cinema; he once wrote to her, “your thoughts and writing about the movies [have] been a very important source of inspiration for me and my movies, and I hope you don't regret that." Kael retired from The New Yorker in 1991, so Anderson arranged for her to have a private screening of Rushmore before the film came out in 1998. Kael later told Anderson, "I genuinely don't know what to make of this movie."
4. Owen Wilson Appears in the Movie.
Although co-screenwriter Owen Wilson doesn’t have a credited role in Rushmore, he does appear as Ms. Cross’ deceased husband, Edward Appleby, in a photo in Appleby’s childhood bedroom.
5. Bill Murray wanted to do Rushmore for free.
Once Bill Murray read Anderson and Wilson’s screenplay, he wanted to be in the movie so badly that he considered appearing in it for free. Murray ended up working on Rushmore at scale with the Screen Actors Guild day rate minimum for smaller indie film projects. Anderson estimated that Murray made about $9000 for his work on Rushmore.
6. Wilson's Dad Inspired a Moment in the Movie.
Wilson’s father, Robert Wilson, was the inspiration for Herman Blume’s speech about privilege at the beginning of Rushmore.
7. Rushmore was Jason Schwartzman’s debut film.
Casting directors searched throughout the United States, Canada, and England to find a young actor to play the lead role of Max Fischer. Australian actor Noah Taylor was the frontrunner for the part when, on the last day of casting in Los Angeles, Jason Schwartzman auditioned. He was wearing a prep-school blazer with a Rushmore Academy patch that he made himself.
8. Be on the lookout for Ryan.
A small boy named Ryan appears as an extra in almost every scene in Rushmore. He can often be found placed between two characters talking or in the background of most scenes. Jason Schwartzman nicknamed him "Dart Boy."
9. One of the Film's Producers Also Had Another Role.
Barry Mendel, one of the film’s producers, also served the hand double for Max in close-up shots. Mendel and Schwartzman have very similar builds and hands.
10. Schwartzman's Phantom Planet Bandmates Get a Shout Out.
Some of the names on Max’s “Save Latin” petition are members of Schwartzman’s former band Phantom Planet, including Alex Greenwald, Sam Farrar, Darren Robinson, and Jacques Brautbar. The band’s manager Dan Field also appears on the petition.
11. Anderson's Brother has a Part in the movie.
Eric Chase Anderson plays the architect who designs Max’s aquarium.
12. Owen Wilson's private school experiences inspired some of the movie's plot points.
As a sophomore at St. Mark High School in Dallas, Wilson was expelled for stealing his geometry teacher's textbook (the one that contained all the answers); he went to Thomas Jefferson High School to complete 10th grade. This was the inspiration for when Max is expelled from Rushmore Academy and is forced to attend Grover Cleveland High School.
13. A Wilson Brother plays Coach Beck.
Owen and Luke Wilson’s older brother Andrew plays Rushmore Academy’s baseball coach, Coach Beck. He also appeared in Anderson’s directorial debut, Bottle Rocket, playing the bully John Mapplethorpe.
14. The Movie's Editor Makes a Cameo.
Rushmore editor David Moritz plays the Dynamite Salesman; he sells Max the dynamite and explosives for his stage play “Heaven and Hell” at the end of the film.
15. Mason Gamble Almost Didn't Play Dirk Calloway.
Wilson referred to the character of Dirk Calloway, played by Mason Gamble, as the conscience of the film. Originally, Anderson didn’t want to cast Gamble in the role because of the actor’s previous role as Dennis Mitchell in the 1993 live-action movie Dennis the Menace.
16. Producers Made a Deal to get a Bentley.
Producers needed a Bentley for Bill Murray's character, Herman Blume, but Rushmore’s production budget was only $20 million and they couldn’t afford to rent one. A Houston resident was willing to lend them his Bentley if they gave his daughter a role in the film. Producers agreed; the man's daughter plays an usher who seats Miss Cross at Max’s play at the end of the movie.
17. Robert Yeoman is a Blue Devil.
On days off, the crew would play basketball at a hotel in Houston. The film’s cinematographer, Robert Yeoman, played for the Duke basketball team during his freshman year.
18. Anderson's Brother Did the Movie's Criterion Collection Artwork.
Rushmore / Flickriver
Eric Chase Anderson did the artwork for the Criterion Collection DVD cover, an interoperation of a shot from the montage of Max’s extracurricular activities at the beginning of the movie. The Yankee Racer shot is itself a re-creation of a photo from French photographer Jacques Henri Lartigue, taken in 1909 when he was only 15. Two of the three racers in the background are Wes Anderson and Wilson.
19. Rushmore Upset Francis Ford Coppola.
Director Francis Ford Coppola owns a winery, and when he first saw Rushmore, he was upset with Anderson because he used Coppola’s chief Napa Valley wine rival during Max’s post-play celebration.
20. Schwartzman waxed his chest to play Max.
Although Max only shows his chest once in the film (during the high school wrestling match), Anderson made Schwartzman wax his chest for the duration of Rushmore's filming.
21. The Max Fischer Players Appeared on MTV.
During the 1999 MTV Movie Awards, the Max Fischer Players re-created the year's hit movies—The Truman Show, Armageddon, and Out of Sight—as stage plays.