A shot of Max Fischer sitting on a go-kart wearing a pair of goggles (and featured on the back cover of the UK DVD) 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. The two people go carting in the background are director Wes Anderson and Owen Wilson.
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.
Rosemary 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.
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".
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 starring Jodie Foster and Helen Hayes. Touchstone is a division of the Disney Co.
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.
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. Not a high school problem, but definitely not the hardest geometry problem in the world.
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.
The film was originally going to be made by New Line 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 $10 million was agreed upon.
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 $75,000 - he gave Anderson a blank check to cover the cost.
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 Supporting Actor.
Before the film's theatrical release, 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 80 and being treated for Parkinson's disease.
Director Wes Anderson drummed up publicity the old-fashioned way by traveling across the country in a tour bus that was kitted out with two big screen TVs, two VCRs, a CD player, cellphones, a satellite dish and a Sony Playstation. This largely came about because Anderson hates to fly.
Max asks Margaret Yang 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, and the girl in glasses was played by Jason Schwartzman's mother, Talia Shire. Max's conversation with the Headmaster, asking to let him stay at Rushmore "for old times' sake," mirrors a similar scene in The Godfather, 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 which, like The Godfather, was directed by Shire's brother, and Jason's uncle, Francis Ford Coppola.
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.
[Charlie Brown Christmas]
Max's dad is a barber, as was Charlie Brown's & "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. In the beginning of the "December" sequence in the barber shop, a musical interlude from that cartoon can be heard playing in the background.