Matthew McConaughey as Willis Newton

Skeet Ulrich as Joe Newton

Ethan Hawke as Jess Newton

Vincent D'Onofrio as Dock Newton

Dwight Yoakam as Brentwood Glasscock

Gail Cronauer as Mia Newton

Julianna Margulies as Louise Brown

Jena Karam as Orphan Singer

Casey McAuliffe as Orphan Singer

Regina Mae Matthews as Orphan Fiddler

Lew Temple as Waiter

Charles Gunning as Slim

Glynn Williams as Farmer Williams

Charles 'Chip' Bray as Bank Teller

Chloe Webb as Avis Glasscock

Gary Moody as Crooked Banker

Robert Iannaccone as Tailor

Jennifer Miriam as Catherine

Anne Stedman as Madeline

Marjorie Carroll as Old Woman

Katie Gratson as Young Hotel Clerk

Angie Chase as Kat

Lynn Mathis as Arthur Adams

Becket Gremmels as Lewis

Ken Farmer as Frank Hamer

Scott Roland as Bank Messenger

Rooster McConaughey as Tool Pusher

Ed Dollison as Night Guard

Boots Southerland as Wagon Driver

Bo Hopkins as K.P. Aldrich

Tommy Townsend as Omaha Detective

Mary Love as Hotel Maid

Zeke Mills as Old Usher

Abra Moore as Argosy Ballroom Singer

Lori Heuring as Flapper

Joe Stevens as Bank Association President

Eddie Matthews as Bank Messenger

Jeff Schwan as Bank Messenger

Bo Franks as Barker

Ali Nazary as Thug

Ron De Roxtra as Murray

David Jensen as William Fahy

Brad Arrington as Hobo

Richard Andrew Jones as Engineer

Randy Stripling as Fireman

Harold Suggs as Old Brakeman

Chamblee Ferguson as Head Postal Clerk

F.W. Post as Postal Turkey

Grant James as Gangland Doctor

Mark Fickert as Chicago Sergeant

Kerry Tartack as Chicago Detective

Luke Askew as Chief Schoemaker

Blue McDonnell as Nurse

Eduardo Cavazos Garza as Mexican Cab Driver

Danny Kamin as District Attorney

Ross Sears as Judge

Johnny Carson as Himself (archive footage) (uncredited)

Rebecca Davis as Dancer (uncredited)

K. Todd Lytle as Toronto Bank Clerk (uncredited)

Hallie Martin as Party Girl (uncredited)

Scarlett McAlister as Party Girl (uncredited)

Christopher Meister as Courthouse Reporter (uncredited)

King Orba as Railroad Hobo (uncredited)

Gavin Perry as Party Guest (uncredited)

Steven Phillips as Man in Movie Theater (uncredited)

Vincent James Prendergast as Kid in Movie Theater (uncredited)

Bobby Shue as Theater Attendant (uncredited)

Jenny Tesler as Secretary (uncredited)

Amber Lea Voiles as Joe Newton's Date (uncredited)

Tara Wood as Cigarette Girl (uncredited)