George Clooney (Captain Billy Tyne), Mark Wahlberg (Bobby Shatford), Diane Lane (Christina Cotter), John C. Reilly (Dale Murphy), William Fichtner (David Sullivan), Bob Gunton (Alexander McAnally III), Karen Allen (Melissa Brown), Rusty Schwimmer (Irene 'Big Red' Johnson), John Hawkes (Mike 'Bugsy' Moran), Allen Payne (Alfred Pierre), Mary Elizabeth Mastrantonio (Linda Greenlaw), Michael Ironside (Bob Brown), Christopher McDonald (Todd Gross), Cherry Jones (Edie Bailey), Janet Wright (Ethel Shatford)