The General (1927), Buster Keaton's silent classic, is regarded not only as one of the greatest comedies but as one of the greatest films of all time. Although the story deviates considerably from the actual events of the Andrews Raid, The General is a fantastic movie—one of the most expensive of its time—filled not only with ingenious comic set pieces, but also dangerous stunts (performed by Keaton himself), battle sequences involving hundreds of extras, and a spectacular locomotive crash into a river gorge. Critics liken Keaton's vision to a Matthew Brady photograph from the Civil War era. "Buster Keaton," Roger Ebert wrote, "was not so much the Great Stone Face as a man who kept his composure in the center of chaos." The same could perhaps be said of James Andrews himself.

Walt Disney's The Great Locomotive Chase (1956), starring Fess Parker, Jeffrey Hunter and Slim Pickens, is an adventure story that reflects Disney's love of trains. (Legend has it that Uncle Walt flipped a coin to decide which to make first: The Great Locomotive Chase or 20,000 Leagues Under the Sea. 20,000 Leagues won the toss.) In some respects, Disney's film remains true to the facts of the Andrews Raid—for example, in showing the progression of William Fuller's pursuit, from running on foot to a railroad hand-car to a succession of three locomotives. But elsewhere, the movie takes considerable historic license and layers on some cinematic derring-do—burning bridges, whooping Rebel cavalry, and Andrews himself leading a fistfight and an escape from the Atlanta jail.