Matthew McConaughey plays Willis Newton, the leader of the Newton Gang who orchestrates a series of successful bank robberies.
Skeet Ulrich portrays Joe Newton, one of the Newton brothers involved in the bank heists planned by Willis.
Ethan Hawke takes on the role of Jess Newton, another member of the Newton Gang seeking excitement and wealth through criminal activities.
Vincent D'Onofrio stars as Dock Newton, the brother who uses his mechanical skills to assist in the gang's robberies.
Dwight Yoakam portrays Brentwood Glasscock, a criminal associate of the Newton brothers who aids them in their heists.
Gail Cronauer appears as Mia Newton, a family member of the Newton brothers who supports them in their endeavors.
Julianna Margulies plays Louise Brown, a character involved in the lives of the Newton brothers during their criminal exploits.
Jena Karam portrays the Orphan Singer, a minor character in the movie who has a brief appearance.
Casey McAuliffe appears as an Orphan Singer in the film, contributing to the background atmosphere.
Regina Mae Matthews is featured as the Orphan Fiddler, adding to the musical elements of the movie.
Lew Temple has a small role as the Waiter, a character who interacts briefly with the main cast.
Charles Gunning appears as Slim, adding a minor character to the overall setting of the film.
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