THE PORTLAND that Gus Van Sant documented in the '80s and '90s is gone. Watching Mala Noche, Drugstore Cowboy, and My Own Private Idaho is like playing bingo with the past: that's where Satyricon used to be; there's a sports bar on that corner now; that street's name has changed.

Portland's changed entirely since Van Sant shot those iconic films. (It's probably annoying for recent transplants to constantly hear about the rough old years in Portland; it's also annoying for longtime residents to no longer be able to afford to live here, so it cuts both ways.) We'll never be closer to the Portland that Van Sant captured in those films than we are at this moment, though, so maybe now is as good a time as any for a retrospective of Van Sant's work.

The NW Film Center has assembled a lineup of notable films directed by Van Sant—the three mentioned earlier, as well as Milk, Gerry, Elephant, and Last Days—alongside work by his major influences, including Werner Herzog, Stanley Kubrick, and Andy Warhol. (The retrospective coincides with "Essential Gus Van Sant," a NW Film Center course taught by Conversations with Gus Van Sant author Mario Falsetto.)

Watching multiple Van Sant films back to back, it's striking just how unusual his choices are. No one set movies in Portland in the 1980s; no one made movies about gay street kids. Gay icon Harvey Milk might seem an obvious choice for a biopic subject, but Van Sant's 2008 film spends long scenes endearingly in the weeds of San Francisco city politics, from voter registration and redistricting to backroom haggling over pet projects. Elephant, Van Sant's 2003 take on the Columbine shootings, is ostensibly about a massacre, yet it's really preoccupied with the day-to-day lives of high schoolers, and the ways different people occupying the same space can have radically different experiences. The perspective Van Sant offers is just a little off-kilter, a little unexpected; his films are marked by an enduring curiosity, an ability to find and tell stories that others might not even notice.

They can also be obstinately impenetrable—since its release in 2005, I've failed more than once to make it through the mumbly, Kurt Cobain-inspired Last Days. Van Sant's debut feature Mala Noche (1986) remains a touchstone of queer and indie cinema, but it's not all that much fun to actually watch; based on the autobiography of Portland poet Walt Curtis, it's a dense, exasperating, claustrophobic look at romantic obsession.

But Van Sant is more than capable of levity, and his movies pop with moments of wry visual humor: the porn magazines that come to life in My Own Private Idaho, the animated pill sequences in Drugstore Cowboy, or the phone tree that represents Harvey Milk's activation of the gay activist community in Milk.

There are a few notable omissions from Northwest Film Center's lineup—it would've been great to revisit Van Sant's relative blockbusters To Die For and Good Will Hunting on the big screen. (Flashback to that strange moment in 1998 when Elliott Smith wore a white suit to sing "Miss Misery" at the Academy Awards.) But most of his best films are here. Whether you're interested in excavating Portland's past or catching up on Portland's most notable director, this is the place to start.