Midnight Cowboy (1969)

Texan Joe Buck (Jon Voight) travels to New York to make some easy money as a hustler - a male prostitute with rich old ladies in his sights. Beneath his veneer of cocky confidence is an unsettled soul with an inflated sense of his own abilities. He befriends a sickly con man played by Dustin Hoffman and the two men eke out a living of sorts in a city populated by lonely people.
The two leads each give wonderful performances, making their unrefined characters oddly sympathetic, but it's the manner in which the film is assembled that really impresses. The addition of flashbacks and occasional imagined scenarios worked in tandem, an undercurrent of feeling that showed how emotional wounds aren't tied to one place or time; they travel with us no matter where we go, for as long as we allow them passage.

3½ shoes shined out of 5