The Man in Black - Jeremy Irons or Anthony Hopkins
Jake - the boy from “Signs” (don’t know his name)
Eddie - I don’t know who could play a convincing heroin addict that isn’t already dead.
Young Roland (don’t blast me!) - Leonardo DiCaprio
Roland - Timothy Olyphant (or Jim Caviezel as above post)
Eldred Jonas from Wizard and Glass - Ian McShane
Still thinking on more.
Only problem with that is Hopkins played Ted Brautigan in "Hearts In Atlantis." If the character is reintroduced in the Dark Tower movies (as he is in the book), I'd like to see Hopkins stay in the role.
As I was thinking about “Signs”, I think Joachim Phoenix would make a good Eddie.
I don't think anyone even comes close to Michael Chiklis as Cort.
I think David Bowie gets the Man in Black...he's a very under-rated actor, and has the right creep factor.