Here is a Vs. for ya 1911 guys

[Clutch]

Michael Sullivan is Tom Hanks' character from Road to Perdition.

John Smith was portrayed by Bruce Willis in Last Man Standing.

I say that Smith wins the encounter, though Sullivan punches him pretty deep in the shoulder before going down.

[S&Wshooter]

Sullivan is already dead and one of the universal laws of movies is that Bruce Willis never dies in an action movie EVAR

[BurtReynoldsMoustache]

Originally Posted by S&Wshooter

Sullivan is already dead and one of the universal laws of movies is that Bruce Willis never dies in an action movie EVAR

The Jackal

[S&Wshooter]

Originally Posted by BurtReynoldsMoustache

The Jackal

It seems that I forgot that movie existed

[AdAstra2009]

Grindhouse

[Yournamehere]

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.

[AdAstra2009]

The Sixth Sense

[BurtReynoldsMoustache]

Death Becomes Her