I'm not 50, but since that rule seems to have fallen by the wayside, I guess I can let it slide too, although judging from the timestamps I seem to be a little late to the party. I've always enjoyed westerns. Grew up watching old video tapes of Roy, Hoppy, Gene, and the Lone Ranger. But I'll throw a few favorites out in no particular order.
- Ride the High Country - Loved Joel McCrea and Randolph Scott in this. Wasn't a huge fan of the romantic pair, but the plot as a whole was pretty engaging.
- High Noon - This is one I've seen a lot of conflict over even among fans of Westerns. Lot of folks, including, apparently, John Wayne, considered it Commie propaganda. Be that as it may, it hits all the right notes of a good western drama. Cooper is excellent in the role, and the idea of standing alone for what's right when no one else will stand with you is used to good effect.
- Support Your Local Sheriff - This one is kind of a funky pick, and isn't necessarily a great example of the classic western, but James Garner is so good in this and the film is ridiculously funny. If the Western can be the setting for virtually any genre (including sci-fi/fantasy, apparently, as Cowboys and Aliens oddly demonstrated a few years ago), here it works surprisingly well for comedy. Couldn't stand the female lead, but between Garner, Morgan, Brennan, Dern, and Elam, it works just fine.
- The Magnificent Seven - Dunno how realistic it is, but watching it for the first time while in my teens, I thought it was one of the coolest movies ever made. It's largely cheese, but really engaging cheese.
- Angel and the Badman - More of a B-western, but I doubt you could find a better example of a second-tier western (if such a thing exists). I really dug the idea of the wild outlaw who gave up his revenge and changed his ways for the love of a good woman. That really resonated with me. It's probably my favorite film I've seen the Duke in (it helped that it was made before he put on all his extra weight).
- True Grit - I love John Wayne (I've watched all but two of his old pre-Stagecoach b-westerns if you want proof of that), but I never really gravitated to his version of the story. The trailer for the more recent True Grit adaptation with Jeff Bridges looked interesting, so I watched it and ended up enjoying it quite a bit. I connected with the characters and story in a way that I never really did with the older version.
- Big Jake - Sort of like the Magnificent Seven, this may be cheese, but I never enjoyed watching the Duke more. He was well past his prime, but I don't think he ever had a character that fit his film persona better (including Rooster and Book, the former of which he particularly felt miscast*, although he played the role well and deserved the Oscar).
- Tombstone - Val Kilmer as Doc Holliday alone makes it worth watching. Kevin Costner's epic Wyatt Earp was far too ponderous - if I wanted something that in depth, I'd read a history book. Tombstone hits the watchability factor out of the park.
- Ox Bow Incident - Of all the morality tale Westerns ever made, I'm not sure they've ever done a better one. Dana Andrews is particularly good.
- Shane - Alan Ladd's relatively short height for a leading man aside, this was a good film. Little cheese, no morality tale, just a good ol' western yarn.
* By miscast, I mean that Wayne had a particular character he played and Rooster Cogburn as written was not it. The viewer should feel uncertain of Cogburn's loyalties so that his heroic display in the shootout and riding Maddie back to the doctor isn't so expected of him. Bridges hit that, Wayne didn't. Wayne was very good at playing the character the way he did, I just think the film suffered as a result of it (but then, given the overall quality of the cast, he probably elevated it, being miscast notwithstanding).
I could talk about a lot more John Wayne films that I enjoyed (Liberty Valance, the Searchers, Rio Bravo, etc), but I'll leave it at that. Didn't care much for the Shootist. Wouldn't be even on a top ten favorites of John Wayne, honestly. But then, neither would True Grit (Wayne's version), and a lot of Duke's fans would crucify me for saying that.
Of the old spaghetti westerns, I watched the original Eastwood three. I overall enjoyed them, or at least parts of them. The Good, the Bad, and the Ugly is far too long and drawn out. A Fistful of Dollars feels a lot longer than it is. A Few Dollars More was not really all that memorable to me. Unforgiven (admittedly, not a spaghetti western) was too dark and depressing for me to have much of an opinion on it, and it really didn't make me think much, which made it somewhat forgettable.
I didn't really enjoy any of the James Stewart solo westerns. Loved him on the radio in the Six Shooter as Britt Ponset, but his solo films represented all that I disliked about the western genre, if I'm being honest. The few Randolph Scott films I've seen felt similar, but somehow worked better than Stewart's, although I never really liked Scott all that much (Cooper either, as far as that goes) but I liked Stewart, just not his films.
Someone earlier asked about the best western ever. That seems far too subjective to me for such an objectively worded question. I'm not even sure that any I listed could be called the best western ever, they just happened to be the ones that most interested or entertained me. Even picking a favorite among those ten would be tough because they cut a wide range even as westerns. If I was forced to choose a personal favorite, though, among those I'd probably have to go with Angel and the Badman, although that opinion might change next week or a year from now.
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