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5. The Gold Rush (1925) An effortlessly enjoyable film, and a worldwide phenomenon upon its release. It's easy to see why it was such a hit—some of Chaplin's most inspired comedic sequences are found here, including the dance of the dinner rolls, the boiling of the shoe, and the giant chicken. Completely canonical yet unwaveringly fresh.
4. A Woman of Paris (1923) "Because the film was unavailable for decades, it has acquired a reputation that it doesn't quite deserve," writes Dave Kehr in his capsule for this early Chaplin feature, which was released at the peak of his celebrity, but didn't feature his popular character the Tramp. Indeed, this is certainly deserving of a more revered reputation, especially considering its nuanced mixture of humor and pathos and remarkable character complexity, the kind found in his most revered and famous films.
3. The Great Dictator (1940) Among his most divisive films, this political satire is of course notable for its biting depiction of fascism and anti-Semitism, but it's also Chaplin's first true "talking picture," and he capped it off with a scathing political sermon that seemed antithetical coming from the known comic actor. It's one of the most moving screen monologues around, and it took considerable bravery and conviction for Chaplin to knowingly undercut his popular persona; you can hear his voice shivering throughout, the result of true emotion, not mere acting.
2. Monsieur Verdoux (1947) The sharpest and most cynical film of Chaplin's late period (yep, even more than The Great Dictator), a ribald black comedy whose controversial reception irrevocably altered the director's career; the film, as such, was instantly dismissed as a failure. Of course, it's understandable that audiences of the time would dismiss the film as categorically "un-Chaplin" (the Tramp, or some kind of vague, Tramp-like character, is nonexistent here), but decades of reevaluation has cemented the film as among the director's most personal and forthright achievements.
1. City Lights (1931) My favorite Chaplin film—one of my very favorite films ever—and not merely because of its brilliant, iconic final scene. The film, like all truly great pieces of art, exists in a perfectly crystallized state, impervious to nostalgia and incapable of seeming dated or archaic in any way. Romantic and devastating and superfunny, few films are as in tune with the hearts of its audience and the mentality of its creator as City Lights.