9. Graham Dalton ('Sex, Lies and Videotape,' 1989)
We may take James Spader's signature brand of alpha-creepiness as a given in today's post-Blacklist age, but back in 1989, we had no idea just how potent his vaguely perverse, semi-icky persona would become. (All he needs to do now is show up, fix his dead-eyed stare on somebody and say one line in that bored-by-humanity monotone, and the hairs go up on your arms.) It's impossible to think of Steven Soderbergh's gamechanging indie movie without Spader's take on Dalton, a character who edges toward getting viewers' sympathy yet stops short of actually gaining it. Most actors would have played him as pathetic and openly needy, but still good at heart; Spader uses his boy-next-door good looks and blank affectations to make him seem hollow, jaded, debauched — anything but easily likeable. This is a guy who tapes women talking about sex so he can get it off to it later and not have to deal with messy things like emotional attachment or other people. And the way Spader blithely says "Nothing I can't finish later" when he's "interrupted" telegraphs just how profoundly fucked up this guy really is.