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Funny thing is RDJ really knocked it out of the park with Iron Man. Before that, Iron Man was a really dry character. His book was kind of joyless. After RDJ, The portrayal in all other media actually changed! That's pretty amazing if you ask me.

No other portrayal (Comics, cartoons, etc) has matched Downey's version of the character, though. I wonder if the character could survive someone else in the role.