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Do you perchance know the car that he's sitting on?
I believe it's a Model T Ford. I don't know what year.
Offhand, just as a guess, I'd say it's a very very late Model T (1927-28) or a 1929-1930 Model A Closed Cab pickup. (Just a guess, the fenders look wrong for a Model T. and the real early Model A closed Cab's used Model T Cabs.
It is entirely possible that it's a Chevrolet, Pontiac, Dodge, Plymouth, or something else though, they're real hard to tell apart sometimes in those early years.