It would be unfair to mix the silent comedy features and shorts together in any kind of ranking. The shorts are funnier per foot of film, while the features have stronger characters and more satisfying plots. It may seem odd to list only Chaplin, Keaton, and Lloyd features, when there are so many comic talents to choose from. Even so, it would be best start at the top and work down to the next rung, which would include Harry Langdon, Laurel and Hardy, and Raymond Griffin. Walter Kerr’s book The Silent Clowns is the best introduction (other than the films themselves) to this most creative era of film comedy — so far.
(1) City Lights (1931; directed by Charles Chaplin)
(2) The Gold Rush (1925; directed by Charles Chaplin)
(3) Seven Chances (1925; directed by Buster Keaton)
(4) The General (1927; directed by Buster Keaton and Clyde Bruckman)
(5) The Kid Brother (1927; directed by Ted Wilde and J. A. Howe; starring Harold Lloyd)
(6) Modern Times (1936; directed by Charlie Chaplin)
(7) The Freshman (1925; directed by Sam Taylor and Fred Newmeyer; starring Harold Lloyd)
(8) Sherlock, Jr. (1924; directed by Buster Keaton)
(9) Steamboat Bill, Jr. (1927; directed by Charles F. Riesner; starring Buster Keaton)
(10) The Kid (1921; directed by Charles Chaplin)