1) McCabe and Mrs. Miller
Every film Robert Altman made challenged the norms of whatever genre he chose, and this was probably the best example. Rather than portraying the main character, played by Warren Beatty, as a macho hero who comes to save a small town, like just about every Western before, Beatty plays a completely inept businessman who decides to start a bordello in a tiny mining encampment that’s not even a real town yet. The only reason he manages to keep on his feet is because he meets a prostitute who is way smarter than he is, played by the brilliant Julie Christie. Despite his best efforts to be detached and indifferent, McCabe falls madly in love with Mrs. Miller, and as a result, we get a movie that is way more realistic, delving deep into the emotional price of pretending to be an emotional cypher. On top of the outstanding acting and script, this film also features some of the most amazing cinematography of any Western ever made, and a score by Leonard Cohen. There are a lot of reasons this one is at the top of the list.
2) Shane
Shane is a film I rewatch at least once a year because it’s so impeccably written. Not surprisingly, the script was written by one of Montana’s best, A.B. Guthrie, known for his novels The Big Sky and The Way West (on my list of best books by authors from the West). Guthrie’s script explores the loneliness of life on the prairie without ever addressing it directly, especially in the wonderful performance by Alan Ladd, who plays a crack gunfighter who tries to escape his past by taking a job as a ranch hand with a small time rancher, Joe Starett. But Shane’s past catches up to him when the local bully tries to intimidate Starett and his neighbors into selling their ranches. The scene where Starett’s young son Joey calls out to Shane as he rides away is one of the most poignant in movie Westerns.