Interesting story to these strange double-sided figures...They were acquired a few years ago from a man in San Francisco who actually bought them when he was a kid. He told me the story of how there used to be an old man at the Playland at the Beach in San Francisco, who had a big bucket of branches (that he probably got from Golden Gate Park across the street) and just sat there all day long making figures. He said the old man also made other things like horses, cars, etc. but they were more expensive so naturally the kids couldn't afford them so they opted for the little men figures. You ordered them and then came back to pick them up after the paint had dried. They were 10 cents each.
It seems that it was no coincidence that an artist like this would be at Playland at the Beach. The owner was a man named George Whitney or "Barnum of the Golden Gate" as the Saturday Evening Post described him in a May 20, 1950 article. Pre-Disneyland, "Playland at the Beach" was America's biggest amusement park, which sat next to San Francisco's famed Cliff House, which Whitney also owned. If you can find the original Saturday Evening Post article, it's definitely worth a read. I only have a hard copy of it unfortunately.
Here's a site that has a few images from Playland at the Beach: Click Here.