After watching both Tombstone and Wyatt Earp, if I had to choose one to say to friends, "if you want to see a movie about "Doc Holliday..." I would always choose Tombstone.

-What about Jesse James?
-What about Billy the Kid?
What about other old west tales? Which would be the 'definitive' to recommend?

Well, almost all westerns are going to have a measure of fiction to them, so definitive might be the wrong word. Are you looking for Westerns only based on real life people and events?

Having just watched The Assassination of Jesse James..., I don't know how accurate it was but it definitely gave me an interesting view of the man. Same goes for Butch Cassidy and the Sundance Kid; I don't know if it was that historically or characteristically accurate but it is definitely entertaining and interesting.

The Man Who Shot Liberty Valance

The Shakiest Gun in the West

I'd choose My Darling Clementine.

Good film but also right next to "Birdman of Alcatraz" in the group of highly inaccurate films based on real people and events.

I recommend Walter Hill's The Long Riders, a well-done depiction of the James-Younger Gang and its downfall (and, in a nice touch, all the historic brothers depicted are played by actors who are brothers).

Classic Hollywood never let historical fact get in the way of a good story. To be fair, though, the Holliday brothers' murder-posse rampage in Tombstone is no more accurate than Clementine.

you know, that sounds so interesting, I ordered it a few minutes ago. A "blind-buy," based on your recommendation.

Just saw this for the first time after loving Assassination of Jesse James and loved it. Violent, meditative, and badass: what the Western is best at.

Although

Christopher Guest and Sam Rockwell played Charlie Ford almost the same.

Pat Garrett and Billy the Kid is easily the most naturalistic Peckinpah Western and a fantastic film.

For Jesse James, I go with "Jesse James" starring Tyrone Power, and "The Return of Frank James" -- they aren't very accurate (the latter is almost pure fiction), but they're great fun.

With Billy the Kid, "Chisum" is good for the background of the Lincoln County War, and "Pat Garrett and Billy the Kid" for the aftermath. (Whatever you do, avoid "The Left Handed Gun.")

And of course the first season of "Deadwood" for Wild Bill's death.

the Turner Classic Movies restored edition... is the one to see...

and 'Pat Garrett' is one of my favorites... i was so stoked when the Peckinpah collection came out... got it release day...

'The Long Riders' is a good film...

one of my personal favorite has always been 'Lawman'... very few films are as straight up bad ass as that one... and as realistic about the nature of the law in the west, and the law men... that is my favorite Burt Lancaster performance... Lee J Cobb... Robert Ryan... Robert Duvall... et al... what a cast...

Link to Lawman... i wish there was a better release bu that probably won't happen...

I love Walter Brennan's take on Judge Roy Bean in William Wyler's The Westerner (1940).

Brennan just steals the show from Gary Cooper.

Ah, another fan. Lawman brilliantly did the whole toll that violence takes on men's souls thing decades before Unforgiven.

No doubt that there's inaccuracies in Tombstone like any historically-based film, but it's generally considered the most accurate depiction of Wyatt Earp and the Gunfight at the O.K. Corral on film. My Darling Clementine, on the other hand, is generally considered one of the least accurate depictions of these same subjects on film, if not the least accurate ever made. (For example, in My Darling Clementine, James Earp - Wyatt's real-life oldest brother - is now his youngest brother and is murdering before the gunfight even occurs instead of living for another 50 years like in real life. Also Doc Holliday is killed in the Gunfight at the O.K. Corral instead of surviving it as everyone knows. Any inaccuracies in Tombstone are drops in the bucket compared to ones like these.)

One of the finest Western of all time Shane .

Great cast, Alan Ladd, Van Heflin, Ben Johnson, Elisha Cook Jr. and a very scary Jack Palance.

My favorite western is High Noon. I also highly recommend Johnny Guitar. Great, great film.

though it's not widely known...

'Cowboy' - with Glenn Ford and Jack Lemmon is fantastic...

'Tom Horn' - with Steve McQueen is excellent...

'Crossfire Trail' - with Tom Selleck is excellent...

I think some posters are missing the point of this thread. This is not for recommendations for just good Westerns in general, but for good Westerns that are specifically about real-life people and real events, particularly ones that are considered definitive. So "based on a true story" type stuff only.

A good example, Butch Cassidy and the Sundance Kid - a good Western based on real-life people.