The Coney Island Roller Coaster train is made of fiberglass, not wood, as a 1940s coaster train would be. Fiberglass was introduced commercially in 1936, but it was used mostly as insulation. It wasn't used for applications like roller coasters until well into the 1950's.
Both times that Hooker rides the Coney Island roller coaster, his cap stays neatly in place, on his head, for the entire ride. In reality, that type of coaster can reach speeds of 60-70mph. His cap should've blown off during the first drop.