When Forrester arrives to defend Jamal at the Mailer School, Dr. Charles Bernstein is present in the background (as Dr. Simon). Dr. Bernstein is a real poet and poetics professor at the State University of New York at Buffalo.
Rob Brown got the role after initially auditioning as an extra. Brown had no aspirations of being an actor, and was only hoping to make some money to pay his 300 dollar cell phone bill. But Gus Van Sant invited him to audition for the role of Jamal, and liked his natural ability.
In addition to being based on J.D. Salinger, William Forrester is also heavily inspired by John Kennedy Toole. Toole wrote the book "A Confederacy of Dunces", a mysteriously autobiographical book, but when no one would publish it, he committed suicide in his car. Years later, the book was published and won the Pulitzer Prize.
The sketch used to portray a young Forrester in the New Yorker and on the wall of famous writers at the school is based on a young Sean Connery. The same picture is on a desk in Mark Trevor's house in Another Time, Another Place (1958), in which Connery was introduced to a big audience.
In the opening, the stack of books (presumably Jamal's) is comprised of the following titles: 'Journey to the Center of the Earth', Jules Verne; 'After the Banquet,' Yukio Mishima; 'The Sound of Waves,' Yukio Mishima; 'The Temple of Dawn,' Yukio Mishima; 'The Sailor Who Fell from Grace with the Sea', Yukio Mishima; 'The Viking Portable Chekhov'; 'Philosophical Fragments,' Soren Kierkegaard; 'The Sickness Unto Death,' Soren Kierkegaard; 'Fear and Trembling,' Soren Kierkegaard; 'Marquis de Sade: A Study,' Simone de Beauvoir; 'A Portrait of the Artist as a Young Man', James Joyce; 'Sometimes a Great Notion,' Ken Kesey; 'Finnegans Wake,' James Joyce; 'The Illustrated Man,' Ray Bradbury; 'Fool for Love,' Sam Shepard; 'Discourse on Method and the Meditations on First Philosophy', Rene Descartes.
Joey Buttafuoco's elusive "Night Man" bit part comprises a few seconds of on-screen time as he offers Jamal a flashlight just before Jamal escorts Forrester onto an empty baseball field (R1 DVD Time 1:21:34).
As Robert Crawford places entries for the school writing competition on a desk, some of the essays' authors' names are those of the movie's crew members: James Pollard (Dolly Grip) and Joyce Tollefson (Assistant to Mr. Connery), et cetera (R1 DVD Time 1:30:19).
The song missing from the distributed soundtrack is titled "Gassenhauer" ("Street Song"). It is the background tune used while Forrester rides his bike. Composer Carl Orff (1895-1982), whose rendition is used in the film, gave its possible year of origin as 1536 by lutenist Hans Neusiedler.
Gus Van Sant previously directed a remake of the 1960 classic Psycho, which starred Janet Leigh. Busta Rhymes (Terrell) later starred in Halloween: Resurrection (2002), which featured Leigh's real life daughter, actress Jamie Lee Curtis.
DVD features two deleted choir scenes ("Lacrymosa" and "Lean On Me"). Additionally, the trailer contains a line by Jamal's mother ("Have you seen my son's backpack?") that is not used in the final film.