Nice Guy Eddy! We think that Anthony Anderson would be perfect for the part originally portrayed by Chris Penn. He just seems so nice himself.
Mr. Blonde is a bit of a loose cannon—in the original film, he is played by Michael Madsen. Madsen recently appeared on British Celebrity Big Brother—oh, how the moderately mighty have fallen. Only Stringer Bell, or Idris Elba as apparently The Wire is not actually real life, can rescue Masden's part.
Samuel L. Jackson is sort of an obvious choice for a Tarantino gangster, but we would like Mr. Jackson to play one of the more sympathetic heist-members, Mr. White. We thought about casting Jackson as Mr. Blonde, but we though Mr. White might be more of a challenge, we already know Jackson can play crazy quite well, we've seen Lakeview Terrace (among other things).
For the part of mob boss Joe Cabot, Reitman needs to find an actor with authority—someone who could believably keep Samuel L. under wraps. Might we suggest Danny Glover?
We pick Omar Epps to play Mr. Orange, the undercover cop (sorry if we ruined that one for you) who spends a great deal of Tarantino's film bleeding profusely on the floor.
Full disclosure: this photo is from the 1993 film The Program—Mr. Epps doesn't really look like this anymore, but look at how cute he was!
Poor Mr. Pink, he was always so upset about his alias. We don't know why, we think pink is a perfectly acceptable color for a man—don't let yourself get boxed in by traditional gender norms, Mr. Pink! Generally regarded as the most annoying of the Misters bunch, we would like him to be played by Cuba Gooding Jr. because he sort of annoys us too.