- Matthew Broderick, a friend of writer/director Kenneth Lonergan's, was the first actor cast in this movie. He visited Lonergan at his apartment, read the part of Brian and asked if he could audition for it. Lonergan then told him the part was already his.
- This was Rory Culkin's first major movie role. Lonergan was impressed on the whole with his acting ability, but had such a difficult time getting him to laugh or even smile on camera that he had Mark Ruffalo tickle him a few times.
- The scene with Rudy walking home from school in the pouring rain was created by the local fire department spraying a hose from their highest ladder.
- The pool scene with Terry and Rudy was shot at a real pool hall where the crew often hung out after shooting.
- Mabel the bank secretary was played by J. Smith-Cameron, wife of writer/director Kenneth Lonergan.
- Kenneth Lonergan plays minister Ron in two major scenes counseling Terry at Sammy's house, and then counseling Sammy in his office. Since Lonergan had a lot of dialogue in those two scenes, he turned over the directing to Laura Linney and Mark Ruffalo, respectively.
- Featured in David Sedaris' story "Repeat After Me" in his 2004 book "Dress Your Family in Corduroy and Denim."
- Kenneth Lonergan - a first time director - had protection from studio interference by his executive producer and friend, Martin Scorsese. They had met when Scorsese's then girlfriend Illeana Douglas had auditioned for one of Lonergan's plays.
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: When he first saw it, Kenneth Lonergan was very unhappy with the location scout's choice of a trailer park for the fight scene between Terry and Rudy's dad. After setting up the shots Lonergan realized it actually was a perfect choice, and he now admits that the day he spent filming that scene was the one he enjoyed the most and experienced the least pressure.
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