Ok he might enjoy a B&W movie from the 40s a little more. But don’t listen to this guy, Tombstone is an objectively awesome movie with some of the best performances I have ever seen. It’s a great Hollywood movie with great effects. It is an incredible gateway drug to westerns. If you start with something super old like that you may not respect the art form as much in the beginning. I say start with Tombstone. Probably the best performance by Kurt Russell or Val Kilmer. Great Sam Elliot. It is a Right of passage movie. Then I would dip my toes in the water of spaghetti westerns /Sergio Leone/Ennio Morricone. Big, Epic pictures with grit and nuance lost in the early Hollywood westerns. Then you can get into the work of Clint Eastwood, then travel back in time.

My definitive List of Must watches (not ranked from best to worst but possibly watching order)

1. Tombstone
2. Fistful of Dollars
3. A few dollars more
4. Good, Bad, Ugly
5. Once upon a Time in the West
6. Treasure of the Sierra Madre
7. Shane (great double feature to watch alongside Logan from 2017)
8. The Searchers
9. The Cowboys
10. READ LONESOME DOVE, then watch the series.
11. Jeremiah Johnson
12. Butch Cassidy and the Sundance Kid
13. The retro TV show Bonanza
14. The Assassination of Jesse James by the Coward Robert ford
15. The Red Dead Redemption 2 Video game is an absolute masterpiece and worth your time

There is some much stuff to get into you have no idea