For dominate males:
Boston Legal. Denny Crane and Alan Shore both have two very different types of swagger.
Any movie with James Dean.
Pulp Fiction.

For social dynamics:
Gossip Girl
Real Housewives of *Insert x here*
Jersey Shore

If you're going to watch the above three though... make sure you spend some quality time with the most down to earth, un materialistic women you know afterwards.

How I Met Your Mother. Both Ted and Barney are actually interesting case studies for ladies men. Ted can come off as self-deprecating and a little lame, but he's also very confident and charming. I think the whole 'have you met Ted' thing would work really for a guy like him in reality. The initial vibe he puts out is 'oh god not this again, how lame is my friend', but he asks one or two questions to gain an opening and then finds something very interesting in the girl that he'll authentically compliment her on. And every once in a while when the conversation is quite serious, he'll tease the girl. Classic Push-Pull.
Barney, well Barney's just interesting.