With the exception of the donkey in the foreground, all of these pieces were bought in a Deer Park antique store in December 2000. They were part of a collection crammed into a battered shoe box that was held together with cord. They probably date from the early to mid '60s, though I think the cowboy (a product of the Tim-Mee toy company) may originate from the '50s. All are made of hard plastic apart from the saddle and the indian. The sculpting is overall pretty basic and slightly crude, but they have a charm despite this. The donkey has an action feature: its head bobs & its tail wags when they are touched. This item was a novelty toy and was most likely available in Mom & Pop stores (which often had a gag gift section) or drugstores. Its body is made of a combination of different mixed color plastics & is marked "Made in West Germany", so its most likely from the sixties. He was bought a few years later at a 2003 Oyster Bay garage sale. The setting for this small showdown was a backyard patio and the large rocks were thrown in for good measure. Now, who is Little Jack? I dunno. It could be the cowboy. It may be the indian. It might even be the donkey.