"Stagecoach" (1939)
John Ford's "Grand Hotel" -on-a-stagecoach tipifies every Western convention and cliche. John Wayne makes his talking debut as the Ringo Kid, and he's backed by one of the most memorable casts in film history, including Thomas Mitchell, who took home an Oscar as a drunken doctor, John Carradine as a smooth-as-silk gambler, and Claire Trevor as the hooker with the heart of gold. Watch for the climax - a dynamic chase across Monument Valley-and stuntman extraordinaire Yakima Canutt as an Indian doing crazy horse things.

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"Shane" (1953)
George Stevens' take on the American myth, "Shane" does more to humanize the Western legend than any film before or since. Alan Ladd plays Shane, a gunfighter who is conflicted by the violent past he despises and his inability to escape it. Over the course of the film, he comes to the aid of a group of farmers being terrorized by the local rancher, plays the Lancelot figure in a Camelot-style love triangle, and ultimately engages in one of the most tense gunfights in film history. Ladd is superb, as is the supporting cast which includes Van Heflin as a strong-willed farmer, Ben Johnson as the thug with a conscience, Jean Arthur as the voice of reason, and Jack Palance as one of the most menacing gunfighters to ride into town. Watch for the terrific bar fight sequence.

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"Butch Cassidy and the Sundance Kid" (1969)
Perhaps symbolic of the Western genre itself, the title heroes of "Butch Cassidy and the Sundance Kid" are anachronisms. They're legends in their own time; no longer simply men, they have nothing to do but fade out and take their places in the history books. The problem is, they're not ready to go. Played by Paul Newman and Robert Redford (one of the best cinematic pairings ever), Butch and Sundance are humanized and, more importantly, likeable. This film is one of the earliest "buddy" pictures, and the dialogue of the film is incredibly funny and touching. The cinematography is breath-takingly lush, and the transitions between black-and-white and color are remarkable. The movie (despite the inclusion of "Raindrops Keep Fallin' on My Head") does not seem the least bit dated, and holds its own as one of the best Westerns, best comedies, and best films of all time.

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Other Westerns...
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