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I can't say that I'm evil very often in video games. I think the worst thing I've ever done without feeling bad is hopping in a car in GTA:VC, driving on the sidewalk, and laughing as pedestrians fly in every direction.

Other than that, playing inFamous as an evil guy... but I felt terrible while I was doing it. I mean, like it was almost to the point where I just didn't want to play it. After I did beat it, I started healing random pedestrians and whatnot just so I'd feel better. ;_;