I nominate the bad guy from highlander: End Game. That guy is hilarious. The bad-a** leather jacket with spikes, the mohawk thing, and the tats and piercings. 'You ever play chicken?' Woohoo. If it wasn't for this whole military thing that's probably how I would've ended up. Aside from him, the movie sorta sucks.
either that dude, or the guy from GTA3.
And I agree with everyone about Hillary. She doesn't quite fulfill the bad-a** mystique, but she is very terrifying. Sort of like Sally Struthers in South Park... or in real life.