4. Nicholas Garrigan - The Last King of Scotland
"Keep it in your pants" has never seemed like a more apt piece of advice for anyone than Nicholas Garrigan (James McAvoy) in The Last King of Scotland. Garrigan heads to Uganda and soon becomes the trusted confidante and personal physician of General Idi Amin (Forrest Whitaker). His first dumb move is in aligning himself with Amin at all, given how blatantly clear it is that he's not exactly a good thing for the country. His second mistake is in hooking up with one of Amin's cast-aside, young wives, Kay (Kerry Washington), and getting her pregnant. He plans to give her a secret abortion, but before he can, Amin has her brutally murdered. At the end, Nicholas escapes Uganda by the skin of his teeth, but his actions not only caused an innocent woman to be murdered, but he was essentially giving aid to a man who was nothing if not a savage tyrant. In the history of dick moves, this one is definitely up there.