The film was originally released in February of 2000 to almost universal praise (especially for the performance of Michael Douglas) but with very little fanfare. Paramount, the film's distributor, decided to re-release the film that November with a different marketing campaign that highlighted its strong supporting cast, and hopes that it would garner some Oscar nominations, despite Paramount Vice Chairman Rob Friedman's acknowledgment that no studio had ever successfully re-released a picture that initially flopped.
In the theatrical version James Leer (Tobey Maguire) included Alan Ladd's death in his list of celebrity suicides. After complaints from Ladd's family, Paramount removed the offending line in all future releases of the film, including home video. Because of this, VHS and DVD releases carry a disclaimer, shown before the feature, warning that the film has been edited for content.
All key scenes feature either one of the many actual bridges of Pittsburgh or a depiction (painting, photo, billboard, et cetera) of a bridge in the background. In the DVD extras, Director Curtis Hanson says this is meant to represent the fact that so many of the film's characters are at a point in their lives at which they have to make pivotal decisions about which way to go from then on.
Curtis Hanson is a longtime fan of Bob Dylan, and personally approached the singer about writing a song for his movie adaptation. Dylan complied with "Things Have Changed", which went on to win him an Academy Award.
The combination to the locked closet with the Monroe jacket is 5641. Fifty-six games is the record number of consecutive games that Joe Dimaggio recorded a hit, and forty-one is the year in which he accomplished it.
The term "Wonder Boys," a derivative of the German "wunderkind," refers to someone who has greatly succeeded in their profession or art at an early age. In the movie, Grady applies the term "Wonder Boy" to James specifically. During the DVD extras, Curtis Hanson also applies it to Grady, though not in an entirely flattering way, since in Grady's case, the term refers to his early literary promise on which he has failed to deliver. In Michael Chabon's novel "Wonder Boys" (upon which this movie is based), the term also doubles as the title of Grady's giant unfinished manuscript, and "Wonder" is the last name of the brothers who are the main characters in that book.
In 1998, the white-mink-trimmed suit that Marilyn Monroe wore in 1954, to marry Joe DiMaggio, was auctioned at Sotheby's New York, and was sold over the phone to an unnamed private American collector for 33,350 dollars. Before the auction, the suit's value was placed at twenty thousand dollars.
Bearing in mind the film's interest in Marilyn Monroe, the character of Miss Antonia Sloviak, a tuba-playing transvestite, may be a nod to Monroe's film Some Like It Hot (1959), in which two men disguise themselves as women, and pose as members of an all-female band. (One of the men was played by Tony Curtis, which may have been the inspiration for Antonia's real name Tony.)
One of the reasons why many reckoned why the film failed to find an audience was because of a very lackluster marketing campaign. The original poster for the film was a close-up of Michael Douglas as Grady Tripp looking very disheveled which the L.A. Times said "makes him look like Elmer Fudd".
James Leer's description of heaven as a greenhouse, is a reference to the houses in Zardoz (1974), which features a Utopian society who wore white, and lived in crystal houses, or possibly Made in Heaven (1987), which has the same interesting set design along with scenes in Heaven, which Zardoz does not have.
James mentions his parents live in the town of Carvel. Carvel is the name of the fictional town where Andy Hardy and his family lived in the series of Andy Hardy films from the 1930s and 1940s. While James is watching television at Emily's house, he stops for a minute on Babes in Arms (1939), which (though not an Andy Hardy film) stars Mickey Rooney, who played Andy Hardy in sixteen movies, and Judy Garland, who appeared with Rooney in many of them.
Back-to-back films in which Production Designer Jeannine Oppewall was involved in a film starring Tobey Maguire. The other was Pleasantville (1998), while this film was in pre-production, where she was nominated for an Oscar for the second consecutive year in a row after her work on L.A. Confidential (1997), which was also directed by Curtis Hanson.
When Grady returns to his house to find Terry (Robert Downey, Jr.) throwing a party, the song playing as he enters the house is "Waiting for the Miracle" by Leonard Cohen. This same song plays over the opening credits of Natural Born Killers (1994), also featuring Downey.
The film features three Oscar Winners: Michael Douglas (Wall Street (1987)), Frances McDormand (Fargo (1996)), and the late Director Curtis Hanson (L.A.Confidential (1997)); and six Academy Award nominees including: Robert Downey, Jr. (Chaplin (1992)), Rip Torn (Cross Creek (1983)), Cinematographer Dante Spinotti (The Insider (1999), and L.A.Confidential (1997)), Writer Steve Kloves (The Fabulous Baker Boys (1989)), Editor Dede Allen (Dog Day Afternoon (1975)), and Production Designer Jeannie Oppewall (L.A. Confidential (1997), and Pleasantville (1998)).
The trivia items below may give away important plot points.
Although in the film, Grady allows Oola to keep the jacket, in the Michael Chabon novel upon which this movie is based, Grady returns it to Walter, and then when Grady and Sara get married, she wears the jacket (just as Marilyn Monroe did for her marriage to Joe DiMaggio).
Tobey Maguire and Robert Downey, Jr. play lovers in this film. Both of them would later play lead Marvel superheros in Spider-Man (2002) and Iron Man (2008), respectively. Michael Douglas went on to appear in another Marvel film: Ant-Man (2015). Maguire had previously worked with Ant-Man himself, Paul Rudd, in The Cider House Rules (1999). Maguire & Downey also portrayed actors portraying lovers in a spoof of The Name of the Rose (1986) in Tropic Thunder (2008).
Robert Downey Jr. and Tobey Maguire play lovers in this film. They also play gay lovers that are medieval priests in one of the fake trailers in the opening of the movie Tropic Thunder (2008). The fake movie is titled Satan's Alley.