Matthew McConaughey ... Willis Newton
Skeet Ulrich ... Joe Newton
Ethan Hawke ... Jess Newton
Gail Cronauer ... Ma Newton
Vincent D'Onofrio ... Dock Newton
Jena Karam ... Orphan Singer
Julianna Margulies ... Louise Brown
Casey McAuliffe ... Orphan Singer
Dwight Yoakam ... Brentwood Glasscock
Charles Gunning ... Slim
Regina Mae Matthews ... Orphan Fiddler
Becket Gremmels ... Lewis
Lew Temple ... Waiter
Glynn Williams ... Farmer Williams
Charles 'Chip' Bray ... Bank Teller
Chloe Webb ... Avis Glasscock
Gary Moody ... Crooked Banker
Robert Iannaccone ... Tailor
Jennifer Miriam ... Catherine
Anne Stedman ... Madeline
Marjorie Carroll ... Old Woman
Katie Gratson ... Young Hotel Clerk
Angie Chase ... Kat
Lynn Mathis ... Arthur Adams
Ed Dollison ... Night Guard
Boots Southerland ... Wagon Driver
Bo Hopkins ... K.P. Aldrich
Tommy Townsend ... Omaha Detective
Mary Love ... Hotel Maid
Zeke Mills ... Old Usher (as A.G. Zeke Mills)
Abra Moore ... Argosy Ballroom Singer
Lori Heuring ... Flapper
Joe Stevens ... Bank Association President
Eddie Matthews ... Bank Messenger
Scott Roland ... Bank Messenger (Steve)
Jeff Schwan ... Bank Messenger (as J.P. Schwan)
Rooster McConaughey ... Tool Pusher
Bo Franks ... Barker
Ali Nazary ... Thug
Ron De Roxtra ... Murray
David Jensen ... William Fahy
Brad Arrington ... Hobo
Richard Andrew Jones ... Engineer (as Richard A. Jones)
Randy Stripling ... Fireman
Harold Suggs ... Old Brakeman
Chamblee Ferguson ... Head Postal Clerk
F.W. Post ... Postal Turkey
Grant James ... Gangland Doctor
Mark Fickert ... Chicago Sergeant
Kerry Tartack ... Chicago Detective
Luke Askew ... Chief Schoemaker
Blue McDonnell ... Nurse
Eduardo Cavazos Garza ... Mexican Cab Driver
Ken Farmer ... Frank Hamer
Danny Kamin ... District Attorney (as Daniel T. Kamin)
Ross Sears ... Judge
rest of cast listed alphabetically:
Willis Newton ... Himself (archive footage)
Gene Burns ... Farmer (uncredited)
Johnny Carson ... Himself (archive footage) (uncredited)
Sean Corrigan ... Hotel Guest (uncredited)
Rebecca Davis ... Dancer (uncredited)
Sallie Guy ... Townsperson (uncredited)
K. Todd Lytle ... Toronto Bank Clerk (uncredited)
Hallie Martin ... Party Girl (uncredited)
Scarlett McAlister ... Party Girl (uncredited)
Joe McDuffie ... Omaha Detective #2 (uncredited)
Joe Newton ... Himself (archive footage) (uncredited)
King Orba ... Railroad Hobo (uncredited)
Gavin Perry ... Party Guest (uncredited)
Vincent James Prendergast ... Kid in Movie Theater (uncredited)
Jenny Starnes ... Secretary (uncredited)
Amber Lea Voiles ... Joe Newton's Date (uncredited)
Tom Weirich ... Policeman (uncredited)
Tara Wood ... Cigarette Girl (uncredited)

Four Newton brothers are a poor farmer family in the 1920s. The oldest of them, Willis, one day realizes that there's no future in the fields and offers his brothers to become a bank robbers. Soon the family agrees. They become very famous robbers, and five years later execute the greatest train robbery in American history.

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