- Cast the Expert: George "the Iceman" Woolf is played by Gary Stevens: a Living Legend, Kentucky Derby-winning, Hall of Fame jockey. Stevens retired from race riding in 2005, but returned to the sport full time in 2013, and continued to ride at the highest level (with a couple of breaks in between for knee and hip replacements) until retiring for good in November 2018.
- Dyeing for Your Art:
- Tobey Maguire had to slim down to play Red. Keep in mind that this film is made between Spider-Man and Spider-Man 2 in which he was required to put on some muscles.
- Elizabeth Banks had to dye her blonde hair dark brown to play Marcela Zabala.
- Fake Nationality:
- American Tobey Maguire as the Canadian Red Pollard.
- American Elizabeth Banks as the Mexican Marcela Zabala.
- On-Set Injury: Tobey Maguire injured his back during filming, which nearly cost him Spider-Man 2.
- Playing Against Type: Quintessential Butt-Monkey Straw Loser William H. Macy as a fast-talking, charismatic radio host.
- Posthumous Credit: Royce Applegate, who had a minor role as Dutch Doogan, was killed in a house fire six months before the film's release.
- Produced by Cast Member: Besides playing Red Pollard, Tobey Maguire was one of the film's executive producers.
- Romance on the Set: Tobey Maguire met his jewelry designer wife Jennifer Meyer on the set.
- Those Two Actors: Tobey Maguire and Elizabeth Banks are mainstays of the Spider-Man Trilogy (though the second film of the series was not yet released during this film's premiere).
- Underage Casting: Chris Cooper had to be aged for his character to look the part. Because he was over 25 years younger than his character, Cooper's hair was whitened and his hairline was shaved back to show a widow's peak hairline. Cooper, despite being two years younger than Jeff Bridges, was made to appear older in contrast.
- What Could Have Been:
- The second Santa Anita race, as described in the book, is simultaneously one of the greatest and most heartbreaking episodes in Seabiscuit's career, but is missing from the movie.
- Robert Duvall turned down the role of Charles Howard because he was making Secondhand Lions.
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