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Agreed on handsome jack
But I would also have to say the dude from Far Cry 3 (what was his name?) --
"Have I ever told you the definition of insanity?" I think his character was perfect.
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His name was Vaas. He's also one of my favorite villains.
Others include:
Shadow Queen - PM:TTYD
Astronema - PR:IS
Raul Menendez - COD:BO2
Shao Kahn - MK