Are you sure The Good, The Bad, and The Ugly isn't on Netflix? I recall watching it on there no more than five months ago. I'm using the USA version, so that might be why. You should really see it - it's easily in my five favorite movies of all time. Well, actually, I like Fistful of Dollars just as much (it's part of the same trilogy - same character).
Anyway, if he was in Fallout, he wouldnt've been a Courier. He would've been double-crossed by Benny after a deal to split some caps 50-50. He would pursue him and hire Boone along the way. Boone has always reminded me of a more disciplined version of Blondie - maybe it's the fact that they're both the strong-silent type. I think if Blondie would side with any faction it would either be the most profitable one, or the Independent New Vegas/Yes Man.