Well shit I feel like I just got a homework assignment, lol. Okay so films - I think he would be PERFECT for Dean in “On the Road”. Also because he did television too, I could see him doing a miniseries like “American Horror Story” because he usually played characters who were… unstable, lol (I know thats random, but whatever) For the car - I still think he would drive a porsche, or basically anything that went fast.
He would be dating me. Ah I think its hard to guess who he would have dated because I feel like the people he dated in the 50’s were all pretty different… Um lets say Lana Del Rey because of reasons, or maybe someone like Léa Seydoux. I don’t think he would use social media. Scandals? I am also going to pretend that Marlon Brando is also alive in this scenario, and so Jimmy’s scandal would be repeated arrests for stalking Brando and stealing his used tissues out of trash cans. And of course he will become legendary when he dies! Its his destiny. :)