3. Monsieur Verdoux
Chaplin's most criminally underrated film, Monsieur Verdoux is a darkly comic picture that marked the first time Chaplin completely abandoned his famous Tramp character. Loosely based off a real-life story, Monsieur Verdoux was originally set to be directed by Orson Welles but Chaplin thought it would be a brilliant idea for a comedy and eventually bought the rights to it. Monsieur Verdoux is at once an incredibly fascinating character study, a critique on capitalist culture, and a complex, captivating work of art. Henri Verdoux is one of the most charismatic and oddly sympathetic villains in film history, even though his crimes are horrifying. He seduces and marries older women before killing them for their insurance and property. He appears to do this to support his "real" family that live in a pastoral home in the country but as the movie goes on, it becomes more and more clear that he has completely lost his way. Monsieur Verdoux was Chaplin's first commercial and critical failure for a variety of reasons: first, it did not have the appeal of containing Chaplin's signature Tramp character, second, it was much more overtly philosophical and examining than his earlier works, and lastly, Chaplin's reputation had taken a remarkable hit in the preceding years due to what some people saw as anti-american sentiments, a string of paternity issues, and mysterious tax problems. Monsieur Verdoux did have some early champions as famed critic Andre Bazin triumphed it at its release and James Agee, another well-known critic, called Chaplin's performance the best he had ever seen up to that point in time. The film was also one of Chaplin's favorites and subsequent years have seen its reputation grow considerably and I had half a mind to put it number one because of its complexity and daring.