I went with Clint, because his films are more interesting and exciting. They explore more facets of the human experience and ask more questions, some of which can be provocative. I grew up on John Wayne films, as a Gen-X member. Clint came into things in the 80s while I was still young, but they were still replaying more John Wayne stuff on tv reruns until the 90s maybe.
While I respect Wayne's work, I find his films one dimensional and jingoistic, even though I get it more and more the older I get. His films represent a heritage and tradition in America that is lost and been overrun. For that alone, I should have picked him, but I'm human, and thus imperfect, so I picked Clint, as his films represent my (and your) imperfections rather than presenting something that we can't go back to. The more I write this, the more I want to switch my vote.
Side note: My father taught me to sail in Newport Harbor when I was a kid. We would rent something like a 16 foot sailboat and cruise around the harbor. He flew for the Navy, so he had this weird thing about boats and nautical shit, but he also loooved John Wayne, as most of his generation did. He was even earlier than Boomer. He was from the Silent Generation, and they were more hard ass.
Anyway, we would sail right past
John Wayne's house in Newport Harbor every time, as his house had a beautiful lawn and dock facing the harbor. He would point it out each time, lol. It was yuge and expensive. He had died not too long before, as this was early 80s, but the house was legit rich people stuff. I still have a picture of it in my head, because it was so memorable.
This picture doesn't really do the house justice, btw. It was a prime piece of property.
Just pure westerns? Clint Eastwood hands down goat
The thing is, though, John Wayne set the standard for what a "pure western" film was. He started out in small roles before he got big, and I remember him talking about how he had to come up with something that set him apart from other actors, so he came up with that walk that looks like he had a stick up his butt.
If we are talking pure westerns, we have to say Wayne, because Clint made anti-hero films, which went against traditional convention on purpose. So, while we may think of that as the standard now, because they are generally more exciting films, Wayne's films are absolutely more "pure western" than Clint's. No doubt.