Yes, we have had discussions like this before on the "Classic Film" board here.... you might try posting it there to get more responses more quickly....
I think James Dean was probably going to be a director, judging from how he was so collaborative with Nick Ray on making "Rebel Without a Cause." Dennis Hopper and others who made the film have said that Dean was essentially the co-director of the picture (which is no insult to Ray -- few directors could collaborate as intensely or productively with leading actors as Ray).
In fact I think his career in that sense would have been very similar to Hopper or to Brando's, although whether he would have more long-term success than either of those men as a director is of course anybody's guess.
A lot of the roles that Dean would have played eventually were played by Warren Beatty, Paul Newman, and Steve McQueen. It's very easy for me to imagine Dean in Newman's role in "Cool Hand Luke", for example, the McQueen role in "The Sand Pebbles", or the Beatty role in Kazan's "Splendor in the Grass." I think your comparison with Jack Nicholson and Eastwood is also somewhat accurate, especially in the sense that both Nicholson and Eastwood were involved creatively in their films.
As far as actresses, it's hard for me to imagine him and Kelly, but I guess if it was built around the contrast between them (Dean was much more emotional and fiery) it could work. I think Dean would have been excellent with, say, Lee Remick. He could have played a role like McQueen's in "Cincinnati Kid" opposite Tuesday Weld and Ann-Margret. He probably would have done other films with Natalie Wood, having already demonstrated such great chemistry with her. Later on, he would have struck some serious sparks with Karen Black.
By the late 60s/early 70s, Dean would have been a bit more rugged (it's hard to imagine a guy like him surviving all those years without some scars), and he would have been sort of an elder statesman to the "hippie" scene. He would have belonged, but at the same time he might have already been too old for roles like Beatty's in "Bonnie & Clyde", and perhaps would have worked his way into character roles depending on the strength of his career at that point.
Did I not love him, Cooch? MY OWN FLESH I DIDN'T LOVE BETTER!!! But he had to say 'Nooooooooo'
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