I've started watching Westerns lately. I've watched the first hour of The Outlaw Josey Wales, very good stuff. So I have some sound films my list like Stagecoach, Searchers, Once Upon a Time in West, Lawman and Dodge City; but what about the silent era? I've only seen The Great Train Robbery from that part, what else would you recommend?
Then there's the films of Broncho Billy, the first Western movie star, and his competition William S. Hart and Tom Mix. I've no particular recommendation for any of these cowboy movies as they're all pretty short and you could see a handful in less than an hour.
Once you get into Gene Autry, John Wayne and Roy Rogers, you're in the sound era (circa 1929). At that point, see anything by the late, great John Ford, pardner!