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?
Anna North
Dream:
Charlotte Gainsbourg
Reality:

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America's Next Top Model's Shandi Sullivan
Hortense
Dream:
Cate Blanchett
Reality:
Judy Greer
Margaret
Dream:
Tina Fey
Reality:
Danica McKellar
Sadie
Dream:
Fay Wray
Reality:
Carol Kane
Tracie
Dream:
Mariah Carey
Reality:
Zooey Deschanel
Anna
Dream:
Leona Lewis
Reality:
Gloria Reuben (Not really, but there aren't many choices for women with Anna's look)
Dodai
Dream:
Dorothy Dandridge (or Thandie Newton)
Reality:
Somewhere between Kelis and Sherri Shepard. Hopefully closer to Kelis :(
Your turn - with pics! - in the comments.