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Meh, I never really got into Underworld. Aside from Kate Beckinsale's tight leather outfit, it didn't really seem to have much to offer. Now, I Am Legend, aside from a couple of glaring flaws, was really quite good, and I enjoyed it immensely. (It could have been so much better in a few ways, though...)
Will Smith's performance in I Am Legend is enough for me to choose it over Underworld.
I don't remember a thing about Underworld. Legend has many flaws, but it still wins this VS....