Modern Times (1936)

This comedic masterpiece finds the iconic Little Tramp (Charlie Chaplin) employed at a state-of-the-art factory where the inescapable machinery completely overwhelms him, and where various mishaps keep getting him sent to prison. In between his various jail stints, he meets and befriends an orphan girl (Paulette Goddard). Both together and apart, they try to contend with the difficulties of modern life, with the Tramp working as a waiter and eventually a performer.