At Quillette, a list of "Nineteen of the Loneliest Films Ever Made," many of which I haven't seen, but I have seen and really liked the last recommendation:
The Straight Story (1999)Not really about an "outlaw" at all, but a decent old guy played by Richard Farnsworth who wants to see his brother at least one more time. It's set in Iowa and Wisconsin where the real events happened.
It’s David Lynch’s only Disney movie, which is delicately illustrated with scenery that looks like it’s been pulled out of the pages of National Geographic. The story concerns an aging man who travels across the heartland on a dilapidated lawn mower, hoping to reunite with his brother (played by Harry Dean Stanton). It’s not only Lynch’s most romantic film, it’s also the only one where his strange interpretation of Americana becomes almost Rockwellian. There is nothing Lynchian about Alvin Straight, who’s a swisher-smoking wiseman who shares his thoughts over crackling campfires and warm meals—each time his eyes filling up with tears. Though it’s based on an unusual story that made headlines in 1994, Lynch’s interpretation of Straight’s story is elegiac. This is a film about an aging outlaw taking his last ride towards the sunset.
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