Oct. 6, 1989: Matt Dillon removes a crowbar from under his trench coat...

It's weird and maybe a little sad to look back on Gus Van Sant's Drugstore Cowboy, given how much of what it describes is now gone. But for those of us who don't recognize ourselves in Portlandia—or who don't want to admit it if we do—Van Sant's first big feature shows us what the real Portland looked like. The story, about a quartet of thieving junkies, is everything the city was in the 1970s and '80s: funny, tragic, morally complicated, cheap, beautiful and seedy. Even today, despite enormous changes in the urban landscape, you can still catch glimpses of the scrappy, dirty Old Portland depicted here—including that Nob Hill Pharmacy sign now hanging on the side of what's now a sports bar.

Portland's most successful home-grown director has gone on to make some wonderful films set elsewhere while still living here. But Drugstore Cowboy, more than any other film ever shot in the city, shows what made Portland unique. Not just physically—Benson Bubblers, Tom Peterson commercials, Union Station, Multnomah Falls—but in spirit. Van Sant's crew of addicts in Drugstore Cowboy, led by Bob Hughes (Matt Dillon), operates according to a strict code. They're not slackers or half-employed hipsters. They put in the hours, including overtime, as Bob points out, to maintain their high, and they take pride in being skilled at what they do. There's an element of rigor and craftsmanship to Bob's lifestyle—he just happens to apply himself in a nontraditional line of work. Classic Portland.

Released on Oct. 6, 1989, the movie is dressed in the vintage threads of 1971. Its characters care about their appearances. They keep up their houses. Meanwhile, the cops range from useless to menacing.

But on top of all the ways in which it captures the city, Drugstore Cowboy is just so good. It's hilarious and terribly sad, and it has those goofball hallucinatory floating-hats-in-the-sky moments that should be embarrassing but instead are somehow perfect. Plus, William S. Burroughs.

Like Portland itself, Van Sant seems unwilling to choose between embracing and abandoning commercial success; he jumps back and forth between studio movies and personal projects, just as Portland can't help basking in mainstream recognition even as it mourns and clings to its grittier days.

Did Van Sant define Portland, or was it the other way around? Who knows, but in Drugstore Cowboy, their fates merged.

Becky Ohlsen writes guidebooks for Lonely Planet and is the author of Walking Portland.

From the archives:

Gus, December 26, 2012 cover feature on Van Sant

Just Add Milk, November 12, 2008 cover feature on Harvey Milk