An honest and compassionate look at the life of people on the fringes of society. The drug addicts in this film are a million miles away from the likes of Renton in "Trainspotting". Sure they are addicts, yes they operate in the shadows of life and it's true that they are not the sort of people that you would want to spend an evening with but they are more knowing, sharper and in control than the stereotypical Hollywood "junkie".
Looking at this early Van Sant it is easy to see the origins of some of the familiar themes and motifs; subculture, outsiders, loneliness, strong relationships between male characters that may, or may not, be homosexual (in this film there is a hint of the classic Greek love of the older man for the younger between Bobby and Father Tom (William S. Burroughs). Stylistically too there are hints of things that would come to be familiar in later works; I noticed the use of rolling clouds to acknowledge the passing of time here and in "Gerry" which I watched just a day or so ago and I'm confident that that particular flourish can be found in "Elephant" and possibly "Last Days" too.
The dialogue in "Drugstore Cowboy" is very theatrical at times, almost Shakespearean. In contrast with his "death trilogy" where dialogue is minimal to the point of being almost non-existant it was interesting to see how well Van Sant could write dialogue. Some of the voiceovers from Dillon are particularly well written and poignant.
Matt Dillon is a revelation here as Bobby. After showing early promise in "Rumblefish" and "The Outsiders" his career had, apparently, plateaued with projects like "Rebel" and "Big Town" but here he is super as the paranoid, street smart, sassy leader of the pack. He clearly impressed Van Sant as he returned to him for a role in "To Die For" (which also proved to be a career highlight).