I was looking at The Wastelands yesterday at the illustrations and specifically the one of Roland. Based on that illustration, I think this actor LOOKS like that depiction a lot. Whether or not he could pull off the role, I don't know, but he has the look.
His name is Ty Burrell. He is a main character on Modern Family on ABC and was also in the Dawn of the Dead remake.
I personally think Timothy Olyphant would be the perfect Roland
If I had only been paid for the hours spent casting this movie with friends who have also read these books. Here goes:
Roland - Jeffrey Dean Morgan - (he played "Comedian" in the Watchmen movie, and is easy to make look young and old. Plus he's a great actor).
Eddie - Jason Lee
Jake - Martin Short - hahaha, I kid. As one of my friends said "He who casts movies with his humor has forgotten the face of his father." I really don't have one for Jake
Susan - You could go Halley Berry, but I don't know about that. I think Rosario Dawson would be better.
Narrator - Sam Elliot
Randal Flagg - Don't know the guy's name who played Rorschach in "Watchmen" but he'd be great.
Cort - R Lee Ermey - I'm proud of that one, so I'll say it again
Cort - R Lee Ermey
Father Callahan - I agree with Eastwood on this. Really Eastwood in his youth should hands down be Roland.
Oy - Frank Welkner -(he's done voice work for practically every cartoon voice you've ever watched)
i think james franko, or edward norton would make a good eddie
Halle Berry? Well you've just killed the entire Dark Tower film franchise..hehe
But I have no qualms with your other speculations
I'm still pushing for Hugh Laurie as Roland:
the lovely Angela Bassett for Susannah:
and the kid from Breaking Bad as Eddie could be interesting...
and my dog as Oy (with some minor CG enhancement, of course):
Andy Whitfield for Roland
I agree with Jada Pinkett as Susannah as you need someone that can play both sweet and mean.. age? shes a bit too old I think but could pull it off.
Eddie Dean.. well one he's supposed to be 21, so I would count out most of the actors mentioned in here. Shia? eh.. I did like someones mention of james McAvoy.. You need someone to play a 21 year old junkie from brooklyn.. think about it.
Jake: This is a really important role I think, as the relationship with jake to everyone else is a big part of the story The only person I could think of is Freddie Highmore but even he may be a bit old for the part as Jake is about 12?