Bill Murray genuinely found Keith McCawley and Ronnie McCawley, who play his sons, annoying (much like their screen characters), and many of the scenes where he lashes out at them and insults them were improvised.
On the first day of principal photography, Wes Anderson delivered his directions to Bill Murray in a hushed whisper, so awed was he to be working with the actor. Graciously, Murray deferred publicly to Anderson, helped haul equipment, and when Disney denied a helicopter scene that would have cost seventy-five thousand dollars, he gave Anderson a blank check to cover the cost.
Director Wes Anderson drummed up publicity the old-fashioned way: traveling across the country in a tour bus kitted out with two big screen televisions, two VCRs, a CD player, cellphones, a satellite dish and a Sony Playstation. This largely came about because Anderson hates to fly.
Before the film's theatrical release, co-Writer and Director Wes Anderson arranged a private screening for one of his adolescent heroes, the critic Pauline Kael. The film thoroughly mystified Kael, who at that stage, was retired, nearly eighty, and being treated for Parkinson's disease.
One of the main filming locations was Wes Anderson's former high school, St. John's School, in Houston, Texas. He hired some of the students from the school to play extras and even some major speaking roles.
The shot of Max Fischer sitting on a go-kart wearing a pair of goggles (featured on the back cover of the UK DVD) is a re-creation of a photograph taken in 1909 by French photographer Jacques Henri Lartigue, a child prodigy who started taking pictures at the age of six. The two people go-karting in the background are co-Writer and Director Wes Anderson and Owen Wilson.
DIRECTOR TRADEMARK (Wes Anderson): (Charlie Brown Christmas): Max's dad is a barber, as was "Peanuts" Creator Charles M. Schulz's. Max flies a kite, which Charlie Brown was often seen attempting. Max is seen wearing a winter cap and carrying a plant, similar to a scene with Charlie Brown in A Charlie Brown Christmas (1965). In the beginning of the "December" sequence in the barber shop, a musical interlude from the show can be heard playing in the background.
The film was originally going to be made by New Line Cinema, but they couldn't agree on a budget. Wes Anderson, Owen Wilson, and Producer Barry Mendel held an auction for the film's rights in mid 1997 and struck a deal with Joe Roth, who was then chairman of Walt Disney Studios. A budget of ten million dollars was agreed upon.
Rosemary (Olivia Williams) takes a job at a girls' private school called "The Webster Smalley School for Girls". Webster Smalley is well known for teaching playwriting at the University of Texas at Austin, which Wes Anderson and Owen Wilson both attended.
Max (Jason Schwartzman) asks Margaret Yang (Sara Tanaka) to remove her glasses, and tells her she looks better without them. While this is a staple of many romantic comedies, it was also used in Rocky (1976), and the girl in glasses was played by Jason Schwartzman's mother, Talia Shire. Max's conversation with the Headmaster (Brian Cox), asking to let him stay at Rushmore "for old times' sake", mirrors a similar scene in The Godfather (1972), between Sal Tessio (Abe Vigoda) and Tom Hagen (Robert Duvall). Shire also appeared in that film. Max's play features many similarities to Apocalypse Now (1979) which, like The Godfather (1972), was directed by Shire's brother, and Jason's uncle, Francis Ford Coppola.
The book that Miss Cross is reading to her students when Max first sees her is "Kidnapped" by Robert Louis Stevenson, which follows the growth of David Balfour from a naive young boy to a heroic, experienced man.
Touchstone hadn't planned on releasing the film until February 5th, especially in light of the heavy holiday release schedule, but when they saw the finished product, they rushed it into limited release for one week in December to qualify for Academy Award consideration, specifically Bill Murray for Best Actor in a Supporting Role.
In the geometry class, about which Max dreams, 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. Not a high school problem, but definitely not the hardest geometry problem in the world.
The song featured while the two main characters are sabotaging each other is a live performance from The Who called "A Quick One While He's Away". This was taken from "The Rolling Stones Rock And Roll Circus" show from 1968.
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; she can also be seen in the audience of "Heaven and Hell". Furthermore, one of the names on Max's petition to save Latin is "Alex Bledel."
The scene in which Max buys dynamite, including charging the purchase to an Arizona company, is almost exactly as it was done at the beginning of Heat (1995), when Val Kilmer's character does the same.
The first film collaboration between Bill Murray and co-Writer and Director Wes Anderson. They worked on many more films (Moonrise Kingdom (2012), The Grand Budapest Hotel (2014), The Life Aquatic with Steve Zissou (2004), et cetera).
Max's green corduroy suit is similar to the one worn by Woody Allen at the end of Bananas (1971). In the film, Allen trains with a rebel group, led by a man named Esposito. Esposito is a character in Max's play "Heaven and Hell".
The quote on Max's mother's headstone, "The paths of glory lead but to the grave" is from the Thomas Gray poem "Elegy Written in a Country Churchyard" (line 36) This same quote was the second clue to the treasure in the Disney film Candleshoe (1977) starring Jodie Foster and Helen Hayes. Touchstone Pictures is a division of Walt Disney Pictures.
In the film, Max checks out a book by Jacques-Yves Cousteau, which is what leads him to finding Miss Cross. Jacques-Yves Cousteau is also the main inspiration for the character of Steve Zissou in The Life Aquatic with Steve Zissou (2004), also co-written and directed by Wes Anderson.
Wes Anderson: The first voice that appears in the film and tries to solve the problem to the equation in Max's dream scene. Anderson can also be seen at the part after the play sitting in the background behind Max.