Tobey Maguire

Red Pollard

David McCullough

Narrator

Jeff Bridges

Charles Howard

Chris Cooper

Tom Smith

Elizabeth Banks

Marcela Howard

Gary L. Stevens

George Woolf

Eddie Jones

Samuel D. Riddle

William H. Macy

Tick Tock McGlaughlin

Royce D. Applegate

Dutch Doogan

Chris McCarron

Charley Kurtsinger

Michael Ensign

Steamer Owner

Jesse Hernandez

Male Mariachi Band

Paul Vincent O'Connor

Bicycle Supervisor

Ed Lauter

Charles Strub

Michael O'Neill

Mr. Pollard

Annie Corley

Mrs. Pollard

Valerie Mahaffey

Annie Howard

Michael Angarano

Young Red Pollard

Dyllan Christopher

Frankie Howard

Matt Miller

Pimlico Starter

Gary Ross

Pimlico Track Announcer

Michael B. Silver

Baltimore Doctor

Jay Cohen

Bugle Player

Cameron Bowen

Pollard Child