Clint Eastwood says the western is the one true art form American cinema can claim as their own. I suggest starting with the older movies and working your way up so you can see how the genre has evolved.
Start with the John Ford/John Wayne trilogy
Stagecoach
She wore a yellow ribbon
The Searchers
(Bonus movie: watch Fred Zinnemann's High Noon)
Next move on to see Sergio Leone's take on the genre with
For a few dollars more
A fistfull of dollars
The good the bad and the ugly
Once upon a time in the west (this movie can easily be found cheap)
(Bonus movie: Check out Once upon a time in America if you get in the mood for a gangster movie by Leone)
The last two movies you should watch are
Sam Peckinpah's The wild bunch
and
Clint Eastwood's Unforgiven
Watching those movies should give you a good overview on how the western has changed over the years.
Start with the John Ford/John Wayne trilogy
Stagecoach
She wore a yellow ribbon
The Searchers
(Bonus movie: watch Fred Zinnemann's High Noon)
Next move on to see Sergio Leone's take on the genre with
For a few dollars more
A fistfull of dollars
The good the bad and the ugly
Once upon a time in the west (this movie can easily be found cheap)
(Bonus movie: Check out Once upon a time in America if you get in the mood for a gangster movie by Leone)
The last two movies you should watch are
Sam Peckinpah's The wild bunch
and
Clint Eastwood's Unforgiven
Watching those movies should give you a good overview on how the western has changed over the years.