Probably Psycho from 1960, since that's pretty good and I thik it is the oldest film I have seen, I started watching a 1920s Dracula but I don't think I finished it
Off the top of my head, maybe1924's Sherlock, Jr.? Buster Keaton is one of the funniest comedians in history, and absolutely mops the floor with Charlie Chaplin.
After watching V for Vendetta I was compelled to watch the 1934 incarnation of the Count of Monte Cristo, starring Robert Donat as Edmond Dantes. It turned out to be a bloody amasing film which had me captivated from start to finish.
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