Okay okay, what about movies where Bruce Willis is the protagonist, does he ever die then?
Anyhow, I thought it was a riddle of some sort and didn't realize you were referring to actual movie characters, but even so the question is meh. Road to Perdition is based more in the real world with regard to guns and physics, whereas Last Man Standing just has 40 round 1911s apparently, so pitting the two characters from their respective universes together is silly.
Ignoring that, Smith would still win every time because it's evident that he has some sort of skill with a 1911. Sullivan has little or none, as he only kills or wounds people at insanely close ranges, usually in a calm, non-tense setting, and he never does it very fast either. When he's not doing that, he's using the 1911 to rob banks or a different, simpler to use weapon like a Thompson. He's not a gunslinger, he's just a mobster, and that makes all the difference.
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