Not Ranked
Tho I don't like his politics I think Tim Robbins could do a good job at playing the lead role: he's tall, and as charming as Shelby was back in the day, and successfully played a baseball player once. You'd have to dye his hair,though, as I think he's gone grey. Or maybe Matthew McConaughey because he's a Texan so wouldn't have to fake the accent but maybe he's better looking than Shelby was during his race driving career. There'd have to be several female leads on account of 5-6 wives (some dispute about this, according to an article in Vanity Fair, Shelby doesn't count the wife he married and divorced in Mexico). If there could be a movie about some crazy New Zealander wanting to set a land speed record on his motorcycle, there could be a movie about Shelby. A good director could be Michael Mann who had good actions sequences in
Heat , Miami Vice and The Aviator
I can recommend a couple books to base it on...
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