- Cast the Runner-Up: Initially, John Sayles envisioned himself in a minor role as a member of the Chicago White Sox. After working over a decade to get the script turned into a movie, he was too old to convincingly portray a ballplayer when filming started. Instead, he cast himself as sportswriter Ring Lardner.
- Dawson Casting: Studs Terkel was 75 when he played Chicago sports writer Hal Fullerton, who was 46 at the time.
- Irony as She Is Cast: D.B. Sweeney, who is right-handed, played the left-handed hitting "Shoeless" Joe Jackson. He initially suggested filming his hitting scenes in reverse, a process used in The Pride of the Yankees. John Sayles didn't have the budget for such effects. Sweeney arranged to work out with a Class A Minor League Baseball team to learn how to hit left-handed. Sweeney came to feel that the conditions and atmosphere around Class A ball were comparable to those around big league baseball in 1919.
- Real-Life Relative: Well, domestic partner - Maggie Renzi, who has lived with John Sayles since he directed his first movie, plays Eddie Cicotte's wife.
- In a straight example, Tay Strathairn, son of David Strathairn, plays the kid who idolizes Buck Weaver.note
- Underage Casting: John Cusack, Charlie Sheen, and D.B. Sweeney were each significantly younger than the players they portrayed.
- What Could Have Been: Michael Biehn turned down a role.
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