Skeet Ulrich as Jack Bull Chiles

Tobey Maguire as Jake Roedel

Jewel as Sue Lee Shelley

Jeffrey Wright as Daniel Holt

Simon Baker as George Clyde

Jonathan Rhys Meyers as Pitt Mackeson

Tom Wilkinson as Orton Brown

Jim Caviezel as Black John

Tom Guiry as Riley Crawford

Jonathan Brandis as Cave Wyatt

Matthew Faber as Turner Rawls

Stephen Mailer as Babe Hudspeth

John Ales as Quantrill

Zach Grenier as Mr. Evans

Margo Martindale as Wilma Brown

Mark Ruffalo as Alf Bowden

Celia Weston as Mrs. Clark

Jeremy W. Auman as Guard

Scott Sener as Guard

Glenn Q. Pierce as Minister

Kathleen Warfel as Mrs. Chiles

David Darlow as Asa Chiles

Zan McLeod as Wedding Musician - Guitar

John Whelan as Wedding Musician - Accordian

Roger Landes as Wedding Musician - Mandolin

Jeffrey Dover as Wedding Musician - Drummer

Tyler Johnson as Wedding Musician - Drummer

Kelly Werts as Wedding Musician - Fiddle

Michael W. Nash as Horton Lee, Sr.

John Judd as Otto Roedel

Don Shanks as George

Jay Thorson as Ted

Dean Vivian as Storekeeper

Cheryl Weaver as Storekeeper's Wife

Amber Griffith as Clark Girl

Ric Averill as Federal at Farm

Buck Baker as Federal at Farm

Donna Thomason as Mrs. Evans

Cassie Mae Sears as Mary Evans

Martin E. Liebschner, Jr. as Encampment Singer

Marvin Schroeder as Encampment Musician

Steve Price as Encampment Musician

David L. Asher as Encampment Musician

James Urbaniak as Poker Player

David Rees Snell as Poker Player

Dave Wilson as Quantrill's Lieutenant

Larry Greer as Federal Captain

Kevin Fewell as Federal Lieutenant

John Durbin as Skaggs

Michael Owen as Federal Recruits Captain

Jim Shelby as Southern Gentleman

Addison Myers as Southern Gentleman

Michael Linsley Rapport as Drunk Raider

Joseph Moynihan as Mr. Riggs

Jennie Nauman as Mrs. Riggs

Christine Brandt as Pleading Woman

Bill Grivna as Dulinski

Nora Denney as Elderly Woman

Harry Gibbs as Old Man

Clayton Vest as Young Boy

Roger Denesha as Lawrence Raider

Jacob Kozlowski as Lawrence Raider

David Lee Burnos, Jr. as Lawrence Raider

Jennifer Ackland as Grace Shelley Chiles

T. Max Graham as Reverend Wright

Sean Whalen as Clark Boy