In early 2000, independent filmmaker Jon Sherman (writer and director of 1996's Breathing Room) adapted Chabon's novel into a screenplay, hoping to film it with Jason Schwartzman in the role of Art Bechstein.

Lecomte, a gay man for whom Art begins to develop feelings, had to be removed because Thurber felt strongly "that in order for the film to function properly, it needed a more efficient and more cinematic engine — in short, a love triangle."

"[7] Miller has been parodied in Pittsburgh media (including one article that was headlined "Semi-famous actress dumps on the 'Burgh")[2] and criticized for making what was seen as an unnecessarily disparaging remark, given the special treatment the film's cast and crew had been given by the visitor's bureau and other city offices.

[10] The site’s critics consensus reads, "A listless interpretation of Michael Chabon's first novel, Mysteries of Pittsburgh features none of the source material's charm, but has coming-of-age film cliches in abundance.

[11] Gay City News felt that the adaptation compromised the "very literary" debut novel and criticized Foster's "cheap voice-over narration" for failing to add any dimension to what's happening on screen.

"[12] Dave White of Movies.com noted that the movie "makes the 1137th film in which Peter Sarsgaard is called upon to play a smug, condescending, somewhat unbalanced, louche, bisexual jerk" and suspected the actor might become typecast.

[13] White added his disappointment with the self-pitying and mopy qualities of Foster's character, and consequently felt the movie played as if "watching Felicity if she were a sexually experimental guy.

"[13] Despite his grievances, White awarded the film a mildly below average C− rating and commented, "I don't want to bash it too much because it's obviously a labor of love from director Rawson Marshall Thurber (he made Dodgeball just to get the cash to free himself to make this)".