1926. dir. Clyde Bruckman and Buster Keaton, starring Buster Keaton, Marion Mack.
Seen it before? No.
Silent movie from way back when. Buster Keaton plays a train engineer living in Georgia in 1861. He tries to enlist in the Civil War, but they won't let him, so his woman breaks up with him. Then some Union spies steal his train, and kidnap the girl, so he chases after them. Hijinks Ensue.
This is a pretty good movie for its era. It's more action than comedy. Keaton is more spastic and physical than the more cerebral Charlie Chaplin, which fits the material well. A lot of the movie is spent in chase sequences on steam trains, and it's pretty clever how it was choreographed. It's all the more impressive when you consider that it was made all the way back in 1926, when there really wasn't much in the way of special effects technology. Pretty sure Keaton did all of his own stunts.
EDIT: Fun trivia from IMDB! "The scene in which The Texas crashes through the bridge was the single most expensive shot of the entire silent movie era."
Daniel watched it with us and he was very upset when the bridge collapsed and fell into the river. He kept saying, "I don't like it!" but I think he actually did because he stuck around for the whole movie.
Position on the list: 137
The music: Added in 2003, and it sucks.