The film was almost accepted in competition at the Cannes Film Festival, but Noah Baumbach refused to cut 15 minutes as they requested, and the film was ultimately rejected.
According to Noah Baumbach at the Lincoln Center anniversary screening, there was another actor scheduled to play the lead role who dropped out at the last minute, prompting Tri-Mark to tell Baumbach to "find a star" or they'd cancel the movie. He quickly faxed his good friend Eric Stoltz, who was filming Rob Roy (1995) in Scotland, and got him to sign on to the movie even though there was no character written for him. They created the character of Chet together, doing a lot of improvisation, in particular the famous "book club" scene.
Jason Blum, Noah Baumbach's college roommate who was producing a film for the first time, obtained financing after receiving a letter from family acquaintance Steve Martin endorsing the script. Blum attached the letter to copies of the script he sent around Hollywood.
Based on Chet's comments in the first book club meeting with Otis, the book is "All the Pretty Horses" by Cormac McCarthy. The movie was released in 1995, and McCarthy's novel won the National Book Award in 1992.