49. Vaas Montenegro
The most memorable video gaming enemies are those you love, and recall fondly, despite the need to bring about their demise. M Bison. Andrew Ryan. Psycho Mantis. Far Cry 3 might not be revered like Street Fighter, Bioshock or Metal Gear Solid, but its lead antagonist merits mention in the same breath. In Vaas’ drug-addled brain, it’s those he’s holding to ransom on Rook Island who are the lunatics. He seems to genuinely believe that offering "two grand to the first motherfucker to bring me Jason Brody's nutsack” is totally normal, and even funny.
Iconic Moment: His monologue on the definition of insanity, which might vary somewhat from your usual clinical diagnosis. "Did I ever tell you what the definition of insanity is? Insanity is doing the exact... same fucking thing... over and over again expecting... shit to change... That. Is. Crazy." Vass would know.