I played L.A. Noire. Who's the "boss" in that? Because if that means I have Roy Earle, there aren't even words to describe the physical atrocities I would inflict on both myself and others. I literally cannot think of a worse human video game character to have as a boss.
Man, I got so screwed over in this thread. At first I thought my last game was BioShock, and I was all ready to type out how yeah, Andrew Ryan would probably be a total slavedriver, but at least I could listen to his lovely voice, and how Fontaine probably wouldn't give a fuck what any of his employees did, but then I realised it was L.A. Noire I'd played instead. Screwed. Over.
(Although if I had Captain Donnelly as a boss, that would be FUCKING AWESOME.)