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I'll start.
Leonidus (300) vs Aragorn (Lord of the Rings)
EDIT: Good post by the way Chris, its getting people talking and some funny answers which is always good.
Cole (Gears of War) vs Bobba Fett (Star Wars)
How about;
Mario vs Luigi??
Here's one: Agent 47 (from Hitman) vs Sam Fisher (Splinter Cell)