5. The General (1927)
Chaplin vs. Keaton is one cinematic argument that will probably never end as the two silent stars approached perfection in their art form almost effortlessly. The General is often considered Keaton's best film and in addition, it features some of the most impressive stunt work of any film, regardless of era. Set in the south during the Civil War, The General follows Keaton's engineer as he pursues a train full of union soldiers who have kidnapped his sweetheart. Essentially the entire film revolves around the pursuit, which eventually flips with Keaton's train being chased back to southern lines by Union forces. Initially poorly received because of its repetitive nature, the General might now be the best regarded silent comedy of them all. Its ability to remain entertaining while taking place almost entirely within the confines of a train, its nearly perfectly timed stunt work, and its brilliant comic touch make it hold up extremely well even today.