
Unlike most self portraits where the subject's expression looks as if it could be held for a long time, Caravaggio captures (and freezes) an expression which could only be held for a quick second in reality. I think it would be funny to watch an artist paint himself while while holding an expression as jarring as this one. I also can't imagine how he could do this without his jaw cramping. He must have used two mirrors so that he could draw his eyes not looking directly at himself.
I believe that by associating himself with Medusa, Caravaggio's portrait sends a message to his viewers, perhaps something along the lines of: "I am an artist. Whoever I draw will be captured and frozen in time." This is essentially the definition of what a portrait is - an image that captures some aspect of the person. Perhaps Caravaggio was into self-mutilation.
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