I think I would need Johnny Depp to play me. He's an awesome actor, with the capability for very broad acting- and i'm a very broad character, i'm constantly all over the place. lol
My last girlfriend would be played by Keira Knightley, which is not meant to be a compliment, it's because she was really skinny. My ex before that would be played by jennifer connelly whom she actually kinda looks like, and shares the same incredible cuteness- but with bigger boobs than jennifer

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Fred Willard would play my dad, and my mom would be Ellen Burstyn. Fred Willard for his wonderful sense of comedy and personality, and Ellen because she's just a class act all the way.
My best friend would optimally (as the perfect in-joke) be played by Leonardo Dicaprio, though in the interest of everyone not instantly hating the movie before even seeing it, perhaps it'd be better if he was played by Ryan Reynolds. Just a very cool, funny guy.