Oh, come on. Like you've never thought about it.
Okay, so you have two categories. "Dream" and "Reality." Your "dream" casting is who you would want to play you; your "reality" casting is who would end up playing you, because they actually look like you. Get it?
America's Next Top Model's Shandi Sullivan
Gloria Reuben (Not really, but there aren't many choices for women with Anna's look)
Dorothy Dandridge (or Thandie Newton)
Somewhere between Kelis and Sherri Shepard. Hopefully closer to Kelis :(
Your turn - with pics! - in the comments.