Well, for the coolness factor, I suppose Harvey Keitel comes close
In terms of humour and everyday behaviour, I think Jerry Seinfeld would be accurate. Don’t get me wrong, I’m not nearly as funny, but I do get into all sorts of inane discussions and debates with my friends. You know, like the “backing into a parking space is the only Right Way” debate.
When going through customs in LA once the security guy was CONVINCED that I was Ashley Judd (I wish) and kept asking me about new magazine covers etc. (no matter that he is looking at my passport seeing ANOTHER name) So in honour of that very great moment, (did a lot for my self esteem) I think Ashley Judd can play me in Straight dope - the movie.
In terms of being closer to actual character, probably Janene Garofalo.
Mario Lopez of Pacific Blue. Only because he’s my current object of desire, and well i want to be played by someone hot :). To look like him i’d have to gain muscle and lose weight (we got the hair color and skin tone thing down ;)), but well, it’s a movie anyway.