William H. Macy

Tick Tock McGlaughlin

Jeff Bridges

Charles Howard

Robin Bissell

Executive Producer

Elizabeth Banks

Marcela Howard

Gary Barber

Executive Producer

Chris Cooper

Tom Smith

Tobey Maguire

Red Pollard

Michael Ensign

Steamer Owner

Roger Birnbaum

Executive Producer

Michael O'Neill

Mr. Pollard

Royce D. Applegate

Dutch Doogan

Ed Lauter

Charles Strub

Gary Ross

Pimlico Track Announcer

Michael Angarano

Young Red Pollard

Michael B. Silver

Baltimore Doctor

Valerie Mahaffey

Annie Howard

Paul Vincent O'Connor

Bicycle Supervisor

Cameron Bowen

Pollard Child

Eddie Jones

Samuel D. Riddle

Annie Corley

Mrs. Pollard

David McCullough

Narrator

Gary L. Stevens

George Woolf

Chris McCarron

Charley Kurtsinger

Jesse Hernandez

Male Mariachi Band

Dyllan Christopher

Frankie Howard

Matt Miller

Pimlico Starter

Jay Cohen

Bugle Player

Allison Thomas

Executive Producer