Gus Van Sant's Portland visions: West Coast urban evolution documented through the viewfinder of a local out filmmaker.

While sizing up the queer streets of San Francisco's Castro District for his latest film, Milk--the story of slain gay rights activist Harvey Milk, expected to hit theaters in late 2008--indie auteur Gus Van Sant was asked his opinion of the City by the Bay. "It's really fun," he replied, "but not as fun as Portland."

The Oregon city of about 550,000 that Van Sant has called home for more than 20 years was once viewed as just a place to gas up on the way to larger and loftier Left Coast neighbors like San Francisco, Seattle, and Vancouver, Canada, but over the past few years this dismissive view has evaporated like the "liquid sunshine" that fails on its streets more days than anyone cares to count. The city's rise in popularity is often attributed to its green mentality--abundant fresh air, mass transport, and recycling. But oddly enough, Van Sant, a gay filmmaker known for his grungy, underground visuals (and blatantly queer outings like My Own Private Idaho and Even Cowgirls Get the Blues), also might have something to do with this image upgrade.

His films reflect the nature of Portland: an organic city that celebrates nonconformity and its status as a place that doesn't give a rip about fame. With its creatives-only vibe, it's attracted plenty of outsiders, including nature-loving lesbians, Gore-Tex gays, and tattooed skateboarders--the same sorts of folks who end up in Van Sant's enigmatic films. Via the Van Sant viewfinder, cinephiles the world over have developed a visual love affair with the city.

The region's wonders are represented throughout the filmmaker's frames (including those trippy opening sequences of time-lapsed, fluffy clouds in Elephant and crashing barns in My Own Private Idaho), but a big part of Van Sant's appeal is his unsentimental, endearing portrait of Portland's fringe culture: hustlers, junkies, crazy poets--the freaky, tranny-chasing, omnisexual hot boys who make Portland hum. You'll find them across the Willamette River from downtown at the Burnside Skate Park (under the south end of the Burnside Bridge, just off Southeast Second Avenue), which doubles as "Paranoid Park" in his latest Cannes-approved opus of the same name, due for limited theatrical release in March.

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At 55, Van Sant is so comfortable within the city's outsider culture, it's surprising that he grew up on the not-so-mean streets of Darien, Conn. He moved to Portland as a teenager in 1970 when his father, Gus Sr., became president of a sportswear company. It wasn't long before he made his first 16-millimeter film with fellow Catlin Gabel School student and future collaborator Eric Alan Edwards. Called The Happy Organ, the 1971 student project hinted at Van Sant's trademarks for telling a story: out-of-synch construction, time-lapse photography, and the whiff of sexual awakening. Although he has worked outside Oregon as well, he has since made at least seven of his films in and around Portland, including his take on the Columbine school shooting tragedy, Elephant (2003), the retelling of Shakespeare's Henry IV through the eyes of street hustlers in My Own Private Idaho (1991), and Drugstore Cowboy (1989), which drifts through the lives of a family of junkies led by Matt Dillon.

After college on the East Coast, Van Sant returned to Oregon in 1985 to make Mala Noche, based on the work of gay Portland street poet Walt Curtis. The $25,000 indie about a convenience store clerk who falls in love with a Mexican boy showed the city in its warts-and-all glory and introduced the outside world to Van Sant's uncompromising viewpoint. "I wanted to make the movie I wanted to see, not the one that I thought would please other people," he said at the time, a drive that keeps him returning to Oregon's unpretentious terrain. "I can't accuse Hollywood of inhibiting my vision."

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Mala Noche was shot just off Burnside Street at a cobweb-covered corner bodega in Old Town, near a punk club where Van Sant and another then-unknown artist, Kurt Cobain, used to play guitar. The frozen-in-amber grocery store has gone buh-bye, replaced by a two-level gay space called Casey's (610 N.W. Couch St.; 503-2249062), where bears belly up to the bar on the first floor and dance deep within the bowels of its dungeon-ready basement.

As with that bygone bodega, finding many of the Portland locales that Van Sant captured on film now requires some imagination-they are dissolving into the ether like so much silent film celluloid. "His stories are authentically set here, not just transposed," says longtime friend Bill Foster, director of the Northwest Film Center and one of Van Sant's earliest supporters. "[But] Portland's become a more affluent place, with the grit replaced by new buildings and the cultural scene invigorated by a new wave of cultural immigrants. I'm not sure that someone who saw every film he's shot here and came looking for 'it' would necessarily find it in the same way that if you watched all of Woody Allen's New York films you would know, if landing there, you were in fact in Manhattan."

Case in point: The greasy porn shops so prominently featured in 1991's My Own Private Idaho are now home to the pricey boutiques and mall shops inside downtown Portland's Pioneer Place (700 S.W. Fifth Ave.). But at Southwest Fourth Avenue and Main Street you'll still find the 107-year-old Thompson elk statue, which regally presided over the famous scene where Keanu Reeves holds a narcoleptic River Phoenix in his arms. Perhaps in homage, Pendleton woolen blankets with stenciled images of the Thompson elk cover guests at the Ace Hotel (1022 S.W. Stark St.; 503-228-2277), a Burnside Triangle gayborhood spot where suites contain D J-ready turntables and bartenders are on call to mix bedside cocktails.

Drugstore Cowboy's central hood, Northwest Portland's Nob Hill district, takes honors for the greatest gentrification. Back in the day this district was affectionately called "Vaseline Flats" due to its proud gay populace. Today, you'll see queers here, but expect more mom-'n'-moms cruising around in their SUVs than cruisy guys. At the corner of Northwest Glisan Street and Northwest 21st Avenue, Van Sant filmed the scene where Matt Dillon and his junkie cohorts rob a pharmacy. The Nob Hill Old Pharmacy Cafe (2100 N.W. Glisan St.; 503-548-4049) still honors the name of its famous predecessor, but now it's a 24-hour coffeehouse where fresh scones, frothy coffee drinks, and free Wi-Fi have replaced pills and ointments. A few blocks west of the pharmacy was another Cowboy locale: Quality Pie, an infamous dirty diner where every drag queen worth her weight in glitter would end a night on the town. It's now an Asian noodle shop, Misohapi (1123 N.W. 23rd Ave.; 503-796-2012).

Tucked in between Nob Hill and Old Town is the Pearl District, which also had more than its share of screen time in Drugstore Cowboy prior to a late-'80s onslaught of bistros, boutiques, chic eateries, and condos. It wasn't called the Pearl back then--it was an industrial landfill, full of secluded hot spots where blue-collar types hooked up with businessmen for a little "relief." It's home to the Lovejoy Columns (Elizabeth Lofts at Northwest 10th Avenue and Flanders Street), old viaduct support beams filigreed with chalk-drawn works of art. They were created by railroad watchman Tom E. Stefopoulos between 1948 and 1952 in a train yard that's now home to the priciest real estate in Oregon. But thanks to preservationists, you can still see two of these pillars, which were cut free and reerected in a plaza a few blocks south of their original site.

Van Sant's connection to Portland's natural beauty shines through in images of Sauvie Island peppering several of his films, including Paranoid Park. Accessible via a 20-minute drive on U.S. Highway 30 (locals often day-trip on bikes), it's the largest non-delta island in the world. Resident farmers share its shores with gay nudists who flock to the beach's west end, just off Reeder Road. (Parking permits are sold at the island's entrance.) "It's one of the most amazing places in Oregon," says Van Sant, who lives on the island. "it's great farmland and a large bird sanctuary. At one time there were 32 dairies on the island; now there is only one." But no matter how much the city evolves, its rough-edged heart and bucolic outposts will never completely vanish thanks to this unassuming director who understands its essence and steadfastly continues to preserve it, forever capturing A Portland on celluloid.

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