Before I go into the real answer, I have to give a shout out to Larry Butz from Phoenix Wright. It's fun that he's a recurring character and that none of the other characters really like him, but damn it, he can even make Phoenix want to beat the crap out of him.
But no, this award goes to someone who really deserves it. I've been playing a lot of Tropico 3 lately, and it really is a wonderfully fun game. It's kind of a messed-up Sim City, where you're a small island nation in the Caribbean in the middle of the Cold War. The events are just as wrong in the campaign mode, too; I've had to choose between people's lives and taking money out of the treasury for my own personal gain. It's a hilarious game. But even in the first mission, you get to meet Betty Boom, the revolutionary DJ on every damn island you go to. Her entire job is to complain about everything you do. I have played a mode easy enough where I could just govern like a nice guy, giving tax breaks and generally keeping the peace. She complains about EVERYTHING.
The world as seen by Betty Boom
This is a true story: in one of my games, my island was so prosperous that I issued a tax cut and I gave the islanders free housing. I was trying to please the capitalists and the communists. Betty Boom complained about BOTH EDICTS. How the hell can you complain about free housing? And whenever I build an army to defend myself from rebels (I've lost because the destroyed my palace), she condemns my trying to protect myself and my citizens.
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