- Acting for Two: Geoffrey Wigdor plays both Young John and Carol's son in a photo in the epilogue.
- All-Star Cast: Robert De Niro, Brad Pitt, Jason Patric, Dustin Hoffman, Kevin Bacon, Minnie Driver, and Bruno Kirby.
- Billing Displacement: Kevin Bacon is billed first, despite a Small Role, Big Impact as Sean Nokes. He's only in the first half of the film, and is killed off after the Time Skip. While the story divides the cast into the child and adult versions of the protagonists, Robert De Niro appears more prominently in both halves.
- Creator Backlash: Brad Pitt is not a fan of his own performance in the film, stating in an interview that he just sees himself doing what other people told him to do, not making the role his own.
- The Danza: Robert De Niro as Father Robert Carrillo.
- Dueling Dubs: The movie has two Latin American Spanish dubs: the original made by Prime Dubb and distributed by PolyGram in 1996, and a second one made by Intersound and distributed for Blu-Ray by Warner Bros.
- Enforced Method Acting: Brad Renfro asked for the floor not to be cleaned when his character had to eat food off the floor because he wanted to "get into it".
- Fake American: British Minnie Driver as a native New Yorker.
- Friendship on the Set: In contrast to the character he played, Kevin Bacon got on very well with the child actors and the extras playing the inmates - to the point where he had trouble reverting to his strict persona during takes.
- On-Set Injury: Kevin Bacon sustained burns from the gunpowder in his death scene.
- Production Posse: Barry Levinson has featured Ralph Tabakin in every film of his.
- Typecasting: The fourth time Robert De Niro has played a priest, after True Confessions, We're No Angels, and The Mission.
- What Could Have Been:
- Early on, Sandra Bullock was attached to play Carol.
- Devon Sawa was offered the role of Young Michael, but had to turn it down due to commitments to Wild America.
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