This blithe young man looks to me to be around 15 to 16 years old. Do you think it is one of the first times he was let off the leash by his parents? The cheeky look on his face in both pictures, but particularly in the pose with the cigarette, suggests, YES! Were these taken to impress a girlfriend, show off to his mates or as an accidental souvenir of his right of passage to adulthood? Whatever the case they were someone’s memento for many decades. Despite being faded, tarnished and stained, the photos radiate youthful joie de vivre some 74 years after they were taken. I can still feel his glee.
From what I have been able to discover, there were many Pennyland centres around the US and Canada offering a large selection of games and coin operated machines to amuse all ages. I think some were stand alone places but more generally they were part of a larger amusement park. The Pennyland where the above photos were taken has long since disappeared, as I can find no reference to it online. Any helpful information from out there would be most welcome!