Its too hard to single out 5 films, but here's my list of 5 favorite Western directors (with my favprites of each in parenthesis):
1. John Ford (The Searchers, Fort Apache, She Wore a Yellow Ribbon, Rio Grande)
2. Sergio Leone (For a Few Dollars More; The Good, The Bad, and the Ugly; Once Upon a Time in the West)
3. Howard Hawks (Red River, Rio Bravo)
4. Sam Peckinpah (The Wild Bunch, Ride the High Country)
5. Clint Eastwood (High Plains Drifter, The Outlaw Josey Wales, Unforgiven)
Everyone has idfferent favorites, but these five directors are essential for anyone wishing to experience the very best the genre has to offer. They are also significant in that they are still known mainly for their Westerns despite directing non-Westerns as well.
While there are many other fine Westerns like Shane and High Noon, their directors did not specialize in the genre and (for me) this puts them at a disadvantage compared to the films of the men listed above. Once Upon a Time in the West gains its power and stature by not only being a prime example of the Western at its best, but also as a culmination of its director's career in the genre. The same can be said of The Searchers for Ford, The Wild Bunch for Peckinpah, and Unforgiven for Eastwood.
Hawks could do anything, but his triumphs in other genres shouldn't take away from the supreme accomplishment that is Red River. His Rio Bravo was also enormously influential, leading John Carpenter to modernize it as Assault on Precinct 13. Together, Red River and Rio Bravo (one in love with wide open expanses of the countryside, the other entirely confined to the saloons and jail houses of a Western town) perfectly encapsulate the two main aspects of life in the West, and Hawks (despite the fact that his reputation would remain intact had he never directed a single Western) deserves inclusion for this fact alone.
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