- Tobey Maguire as John "Red" Pollard
- Michael Angarano as Young John "Red" Pollard
- Jeff Bridges as Charles S. Howard
- Chris Cooper as Tom Smith
- Elizabeth Banks as Marcela Zabala-Howard
- Gary Stevens as George Woolf
- William H. Macy as "Tick Tock" McLaughlin
- Eddie Jones as Samuel Riddle
- Michael O'Neill as Mr. Pollard
- David McCullough as The Narrator[2]
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