Some of these are also examples of something I've started writing about but can't quite get together, which is the movie where the protagonist is a sociopathic white guy with a straight face and wryly destructive sense of humour who in the real world would be loathed by all, but in the movie always gets the girl. Your "sage libertine, I guess." Young Bill Murray was good at these roles, Ryan Reynolds sometimes, Dane Cook too although he could also play the "just dick" who didn't get the girl.