Selected filmography: Finder Forrester (2000), Gerry (2002), Elephant (2003), Last Days (2005), Paranoid Park (2007), Milk (2008)

Gus Van Sant entered the 2000s like a beloved president in the midst of a PR nightmare. On the one hand, he had just three years prior directed Good Will Hunting, a box office smash, the Oscar-winning, feel-good hit of 1997. But he followed up that film with a shot-for-shot remake of Alfred Hitchcock’s Psycho, and it was so universally reviled, Van Sant needed to recoup his clout. Enter: Finding Forrester.

Finding Forrester, a tepid New York-version of Good Will Hunting’s marginalized-genius story, performed strongly enough at the box office to make up for the mistake that was Psycho. This success allowed Van Sant to pursue a bold kind of filmmaking that continued to explore the themes of alienation present in his work from the beginning of his career, but this time with more formally audacious techniques. He threw out dialogue-heavy storytelling and conventional continuity editing for long tracking shots and editing that shattered chronology like a cheap mirror.

While in New York, Van Sant revisited Béla Tarr’s seven-hour-long Sátántangó and Chantel Akerman’s Jeanne Dielman at Anthology Film Archives as preparation before going into the desert to shoot 2002’s Gerry. The first film of his Death Trilogy follows two hikers, both named Gerry (Casey Affleck and Matt Damon), who become lost. Or, should I say, rock marooned?

In addition to flexing a new cinematic grammar, Gerry creates its own vocabulary. The word "gerry" also functions as slang for fucking up and around. Rock marooned is the state of being lost, inexplicably and incomprehensibly trapped atop a tall rock formation. The film is full of bizarre language that distances the viewer from the characters in the same way that they are distinct from nature and each other. Hypnotic, oblique, and funny (if you can get on its level), Gerry was the first step down a path Van Sant would walk for the next five years. Less patient viewers should note that it’s also the most difficult of his movies from this period.

Elephant and Last Days, which dramatize a school shooting similar to Columbine and the death of a rock star like Kurt Cobain, respectively, complete the loose trilogy. Both films engage with the thorniest of subject matter, and come away successful by maintaining a respectful distance from their subjects. The best scene in Last Days enacts this literally: The camera very slowly tracks away from the window of the decrepit mansion in the Pacific Northwest where Blake (Michael Pitt), the film’s Cobain figure, has holed up. Through the window you can just make out Blake as he moves around the room, playing various instruments. He picks up a guitar. A cymbal flashes like a winking cat's eye. Blake puts together a song as the camera moves further and further away. We can’t be there when he makes his art. We can’t access that space. We can't know him.

Neither Elephant nor Last Days try to explain away their tragedies. They don’t psychoanalyze. They don’t speculate. They don’t offer answers. They’re dreamy encounters with terrible things and if they’re about anything it’s the impossibility of understanding in the face of those things.

Van Sant concluded the decade with two powerful statements: Paranoid Park and Milk. Paranoid Park, about a young skater in Portland who accidentally kills a security guard, is of a piece with the Death Trilogy because of its fractured chronology and dialogue-less moments of cinematic ecstasy. Van Sant transforms something as mundane as a breakup between a high-school couple by removing the diegetic sound—that is, the sound actually happening in the scene—and replacing it with bright strings from Italian composer Nino Rota. It becomes sublime.

Paranoid Park stands out as one of the strongest (and most accessible films) from Van Sant’s 2000s output by marrying the more avant-garde style of the Death Trilogy to a strong narrative. Tellingly, Paranoid Park is an adaptation of a YA novel.

Milk, released in October 2008, was Van Sant’s return to conventional moviemaking (albeit on the level of someone of his talents and interests—this wasn’t Michael Bay’s Milk). A biopic about Harvey Milk, the gay rights activist and first publicly out person to be elected to public office in California, the film hit theaters just weeks before the vote on Proposition 8 in California. The amendment sought to ban same-sex marriage in the state. Milk is a beautiful, warm movie released at a time when the country needed Hollywood to say something meaningful. Sean Penn’s performance as the slain politician is charming and heartfelt, as are the supporting performances from James Franco and Diego Luna. Still, the amendment passed.

Thankfully, we can now talk about the amendment in the past tense. A district court’s ruling overturned Proposition 8, and the Supreme Court ruling on July 2013 did not to do anything to change that.

And regardless of what Van Sant does in the coming years, nothing will tarnish his five-picture hot streak during the aughts. —Ross Scarano