Hardest roles in literature to cast

Which are the hardest-to-cast (for film, TV or stage) roles in literature? They can be roles that have already been tried (perhaps unsuccessfully), or roles that seemingly nobody wants to touch.

One that comes to mind for me is Randall Flagg, the uber-villain of Stephen King’s The Stand (and many of his other works). The thing that makes him tricky is that he’s rarely described in close detail, and what detail there is comes in little flashes. Most of the time he’s described through his effects on others and his surroundings. Because of that, almost any film depiction of him is doomed to show too much, thus robbing him of his creepy aura.

Any others?

Well on your note, I’d love to see someone try and cast Roland from the Dark Tower. The only one I can think of that may work is Sam Elliott. But without the niceguy cowboy thing. He’s got the rugged thing going for him, but he would need to be meanied up (if there is such a phrase)

I guess the best choice for Roland would be a 40 year old Clint Eastwood, which King admits he more or less based the character on. A 75 year old Eastwood…not so much. :frowning: