If you like this one, and you haven't heard Sam Cherry's Last Shot, you'll probably enjoy it! Also narrated by Broderick Smith (who is pretty damn badass himself):
Awesome! This is exactly what I wanted, that mans voice is fantastic and King Gizzard really evoke that western film sound, similar to Ennio Morriconne (The Good the bad and the ugly soundtrack composer)
I'm not Kerbobotat, but your friend is right about The Dollars trilogy. The Coen Brothers' version of True Grit is also a treat. Butch Cassidy and the Sundance kid is a lot of fun. Tombstone stands up relatively well as well. Most movies with John Wayne are passable. If you have Netflix, they actually have some westerns from different eras. They're not all the cream of the crop, but you'll get a feel as to how the style and tone of westerns have changed over the years.