The script was developed at the 2002 Sundance filmmaker's lab and was one of the focal points of the Robert Redford produced documentary Sundance 20 (2002), which is an inside look at the lab's process.
During production, Alec Baldwin worked 7-day weeks, splitting his days between the film and the television series "30 Rock" (2006).
The role of Mickey Bartlett was written with Alec Baldwin in mind.
The screenplay is based on the Martini's own childhood.
Emile Hirsch, 'Ryan Gosling' and Kieran Culkin were originally cast in the film. By the time the funding was complete Emile and Kieran had become too old for their respective roles and were re-cast, while Gosling had become too big a star to do a supporting role.
The project was developed during the 2001 Sundance Filmmakers Lab.
The film is loosely based on the Martinis' own childhood experiences.
Kieran Culkin shot experimental scenes as Scott Bartlett. He's since been replaced by Rory Culkin, as he's grown too old for his original role. He'll now play an older brother, Jimmy Bartlett.
While the film was being developed at the Sundance filmmaker's lab, Kieran Culkin played the role of Scott in all of the experimental scenes the Martinis shot. When it came time to make the film for real, Kieran's younger brother, Rory Culkin was offered the role because Kieran had become too old to play it. After reading the script and watching the experimental scenes from the lab, Rory said yes.
Jennifer Jason Leigh had been attached for the role of Brenda Barlett for many years. But when the film finally came into production she wasn't available. Jill Hennessy replaced her.