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- George Clooney as Frank William "Billy" Tyne, Jr.
- Mark Wahlberg as Robert "Bobby" Shatford
- Mary Elizabeth Mastrantonio as Linda Greenlaw
- Diane Lane as Christina "Chris" Cotter
- John C. Reilly as Dale "Murph" Murphy
- William Fichtner as David "Sully" Sullivan
- Michael Ironside as Bob Brown
- Bob Gunton as Alexander McAnally III
- Karen Allen as Melissa Brown
- Cherry Jones as Edie Bailey
- Allen Payne as Alfred Pierre
- John Hawkes as Michael "Bugsy" Moran
- Janet Wright as Ethel Shatford
- Christopher McDonald as Todd Gross
- Dash Mihok as Sgt. Jeremy Mitchell