Rantings of an Arranged Mind

Just putting this out there, because it's fun for me to hear what people think:

If The Surprising Life and Death of Diggory Franklin was a movie, who would you cast?

I'm not going to put up my current preferences yet, because I want to see what people say. But I'd like to hear how people picture my cast. I will give you one, that I can't decide on:

Matt the Pimp: played by Sean William Scott or a younger Owen Wilson?