The Mysteries of Pittsburgh

Earlier attempts to bring Pittsburgh to the big screen failed, including Chabon's own try at adapting the novel. 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.By August of the same year, Chabon announced that the project had fallen apart, sadly writing, "Ah, well. Maybe someday."

Director Rawson Marshall Thurber got hold of the project sometime prior to 2006, when he began filming after convincing Michael Chabon he could make it work. Chabon had seen the script, and was pleased with it. In order to facilitate the film adaptation, Thurber removed the character of Arthur Lecomte "whole cloth" from the original Chabon novel in what he described as "the most glaring change". 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." Consequently, many elements of Arthur Lecomte were folded into the character of Cleveland