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This is Dan Blocker, of Bonanza fame, and he was the owner of a 1965 Huffaker Genie MK10 race car nicknamed "Vinegaroon".The blackface picture is his portrayal of DeLawd in the 1949 movie "Green Pastures".
By the way, he's connected to another race car that is a long-solved puzzle here, for those who care to rummage.