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Tried watching this for the second time. I watched it in high school and thought maybe I would appreciate it more now in my mid 20s. Apparently I'm not smart enough to understand why this movie is generally considered the greatest of all time. Maybe Kicky can explain it to me.
A lot of the reson the movie is considered the greatest of all time by a plurality of film critics has to with a stunning array of technical and storytelling innovations. Particularly famous are the development of deep focus photography, the dark scene in the theater with the only light being provided by the film projector (a direct ancestor of the Third Man's sewer chase lighting choices), and the use of breakaway sets to allow the camera to move through what should be solid spaces.
These are all things we take for granted today but were entirely new inventions at the time.
It helps that the story is pretty good and that Welles' has what the Madame refers to as the "id gleam" in spades for a good chunk of the film until he gets beaten down by life.
It is also the only film that I have ever watched multiple commentary tracks on the DVD version because of the wealth of information available.