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Every Gus Van Sant Movie, Ranked

Through a rich abundance of cinematic styles and genres, the indie and studio auteur never stops finding new ways to tell the same story.
Gus Van Sant On Set Milk
Focus Features
By  · Published on August 10th, 2018

10. Even Cowgirls Get the Blues (1993)

Even Cowgirls Get The Blues

Mostly remembered for being loathed by audiences and critics with such passion that it never inspired the kinds of sarcastic audiences that, say, Showgirls still courts, Van Sant’s first flop merits more thought. It’s an old-school John Waters movie let loose, adrift in the sea of slacker violence and hard edges that ’90s hipsters craved. Its failure to connect with them is doubly sad, as it remains Van Sant’s only attempt to turn his sentimental compassion toward queer women, starring Uma Thurman as a bisexual and large-thumbed model and hitchhiker. If you pay him, Van Sant will do anything twice (see Finding Forrester), so shame on you ’90s kids.

The movie is something like a marriage of On The Road and One Flew Over the Cookoos Nest (an aging Ken Kesey even cameos briefly) and, in that sense, is very faithful to the ’70s pastiche artist whose novel it adapted. Van Sant uses that cartoonish sensibility to fill a road trip with lively surprises, from John Hurt as an insidious gay businessman named The Madame to a labor politics plotline that has more in common with Boots Riley’s Sorry to Bother You than anything else in theaters that decade.

9. Gerry (2002)


Because Ulysses is too damn long, most college students will choose Waiting for Godot instead, which is very thin. Consequentially, there is great (retrospective) appreciation for Gerry, a movie that, like Godot, only has two people in it. They are Matt Damon and Casey Affleck, a casting choice that I personally like to imagine was made because Damon had refused to star in the version of Brokeback Mountain that Van Sant had initially optioned. Van Sant ended up shooting Gerry instead which, like Annie Proulx’s short story, takes place in the barren west and consists of two men spending long amounts of time with each other there. But instead of having sex, Damon and Affleck get aimlessly lost, and when Damon climatically rolls on top of Affleck, he chokes him to death, making the movie the first of Van Sant’s “death trilogy.” Touché.

What Gerry reminds me of most (sorry, Bela Tarr) is that Onion video imagining an ultra-realistic version of the Call of Duty franchise where “the majority of gameplay [is] spent hauling equipment and filling out paperwork.” As it turns out, Van Sant was influenced not by playing video games but by watching other people play old school Tomb Raider, captivated by how much game time was spent walking around. In this way, Gerry is a perfect antidote to today’s abundant action movie long shots, rich tapestries that attempt to provide the same thrill as those Renaissance paintings much admired by high school students. Why not just watch Matt Damon and Casey Affleck walk for six minutes straight?

8. Psycho (1998)

Contrarians consider Van Sant’s version of Psycho to be “realer” than the 1960 Alfred Hitchcock hit film. While they are wrong or maybe just tedious, ditto the conventional discourse that writes the movie off as “a high-budget, obsessive exercise in imitation,” “art forgery” or other variations of the word “experiment.” In a decade where a Who tribute-band called Pearl Jam played stadiums as some kind of collective joke, Van Sant’s Psycho is the quintessential movie of the ‘90s, a cover song coordinated on mass scale. As a rule, remakes insult critics and, twenty years ago, they tripped over themselves to explain why this one couldn’t possibly work.

Van Sant’s eagle-eye targeting of film snobs may be Pyscho98’s most obvious joy, but it also holds up as a kinetic act of cultural criticism, challenging the validity of its source material as much as it refashioned it. As Roger Ebert moaned at the time, Van Sant deliberately de-eroticizes Marion Crane, which reveals how much the original relied on the exploitation fare of watching pretty blondes get what that decade’s audiences thought should be coming to them. And in his casting of Norman Bates, Van Sant rewrites the character completely. Instead of a walking stand-in for the queer panic of the original film, Vince Vaughn’s version of Bates is as handsome and self-assured as any of Van Sant’s leads. Vaughn barely looks like he cares about the whole serial killing thing; in the movie’s one change from the original, Bates is shown masturbating before killing Crane, suggesting the whole thing is one elaborate kink, as chore-like as taking out the trash. Beatrix Aruna Pasztor, Van Sant’s costume designer since Drugstore Cowboy, originally thought the movie was to be a period piece and costumed the movie as such, giving it the dressing of a parody but played without winking. The ’90s were a decade of recovery from the paranoia complex of the Cold War, and in Psycho, it is a breakdown in human relations that Van Sant takes seriously.

7. To Die For (1995)

After his Uma Thurman-starring queer epic was viciously rejected by critics, test audiences and real ones, Van Sant picked up a script about a woman who ends the movie dead at the bottom of an ice rink. In one of Nicole Kidman’s early starring roles (Van Sant cast her, partly, because she “wasn’t an extremely recognizable female lead”), she plays a TV-obsessed journalist who convinces her high school lover (Joaquin Phoenix) to kill her husband (Matt Dillon) and is in turn killed by her in-law’s mafia connections. Despite being the movie’s central figure of gravity, Kidman’s character barely leaves an emotional mark on the heart of Van Sant’s world. In the mockumentary-style footage that narrates the movie, Phoenix’s delinquent character is interviewed serving a 30-year sentence for his involvement, but cannot remember what his seducer looked like.

A satirical murder drama set in the snowy hills of New Hampshire, To Die For is notable for presaging similar sarcastic movies about murder set in wintery locales like A Simple Plan and Fargo. To Die For has more of an earnest drama at its center than either of those, though it is the only tonal outlier in Van Sant’s work, his sole movie with a vacuum of sincerity at its center. Instead, it can be found in its outliers, in the charismatic charm that Phoenix exudes or the way Dillon returns to a Van Sant movie to continue to be sleepily seduced by comfort. That Van Sant also restrains from lending its story the farcically-styled outlines of My Own Private Idaho or Even Cowboys Get The Blues makes the movie’s repeated breakdown of normative romantic relationships feel tragic instead of campy.

6.  Milk (2008)

Milk james franco

As someone constantly working inside the genre, Van Sant is among one of the more arresting architects of the biopic and has done much to restrain the grandiose-by-default genre by using slices of life to tell a story that evokes a whole and lived life. Most directors who have taken after his style have done so very literally, and the current fashion is to precisely excise singular slices of the great lives and pontificate on them, i.e. Selma, Steve Jobs or the upcoming On the Basis of Sex. Van Sant’s idea was always to show their lives in the same style as anybody else’s: collections of small events whose importance is left for an audience to decide.

If you skip the speeches, much of Milk plays like a star-studded version of his earlier movies, complete with its impressionistic style and its focus on the relationships between a privileged artist-intellectual (Sean Penn) and less privileged outcasts, this time from gay society (Diego Luna, Emile Hirsch, James Franco)— David Denby likens them to “lost boys.” In fact, the film was among the first Van Sant tried to do in the major studio system, though creative disagreements in the wake his then-recent box office bomb Even Cowgirls Get the Blues had put his involvement off until he made more money. Most people hate biopics, so Van Sant’s determination to make them in his particular fashion feels strangely brave, an insistence on creating an outsider world for political heroes and junkie criminals alike.

5.  Paranoid Park (2007)

Paranoid Park

Like Elephant, Van Sant populated a high school movie with real high school students, cast this time via an ad placed on MySpace. A kid named Alex (Gabe Nevins) is drawn toward his town’s skater community, literal outsiders gathering at a far side of town. To impress one of them, he leaves his girlfriend and spends a late night between the train tracks, an equally literal signifier of social boundaries. Also like Elephant, an early scene of violence occurs—the two accidentally kill a security guard who discovers them there—and haunts the movie.

The movie is one of Van Sant’s purest expressions of yearning—the skate park that the movie’s title takes after is a sort of heavenly place dreamed about while in school—while dealing with the mundanities of straight life. That the movie rips it away from Alex almost as soon as he makes the dive suggests that the Van Sant film optimally lives in the space between self-consciousness and acceptance. Alex spends much of the movie writing down a confession, ready to turn himself in and turn himself away from the world he fantasizes about. At the end he burns it, tragically willing to live in that cycle forever.

4.  Mala Noche (1985)

Mala Noche

Made on his own hard-saved dimes after working in advertising, it is fitting that Van Sant turned to his adopted hometown of Portland and the story of an unsung beat poet named Walt Curtis. Many of Van Sant’s interests are outlined here: biopics, artists living on society’s edge, the relationships between younger and older men, the wealthy and the impoverished and the queered spaces where they interact. Tim Streeter’s Curtis even delivers a long yarn about wanting to “experience the death” that persists in the everyday lives on society’s edges, a subject that Van Sant would explore further in the “death trilogy” he made in the early 2000s.

The movie’s stream-of-consciousness impressionism would also come to define Van Sant’s approach to subjects, expressing the day-to-day in a series of moments, phrases and closely shot expressions. Van Sant would take this approach toward working with Oscar-winning stars and the lives of rockstars, and it would work because it resisted the epic lilt of the official historian, who stages moments that are meant to make the argument for the movie’s own consequentiality. “A gringo like me has an easy life,” Streeter ruminates briefly, a self-aware throwaway that underlines Van Sant’s own self-awareness.

3.  Last Days (2005)

Last Days

The final of Van Sant’s movies about death, it is possibly his most relentlessly bleak. Unable to relate to the human intimacies that Van Sant has given himself to chronicling, a stand-in for Kurt Cobain (Michael Pitt) walks, where else, but to the grave. The apathetically removed long shots that define Van Sant’s run of indie movies about death make the most sense here: we never catch Cobain jamming to “Smells Like Teen Spirit,” but we see what Cobain looks like when he’s done. Van Sant uses the space of his shots to frame the radical alienation of stardom, hidden behind rockstar hair. It’s the image Cobain saw of himself on TV screens and magazine covers, a figure whose face can barely be parsed, a blur that jumps up and down. “You’re suddenly enlisted in a world that you weren’t part of before. What you had before was just your body,” Van Sant told The Guardian during the movie’s Cannes debut, comparing Cobain’s life to his own early ‘90s ascent.

2.  My Own Private Idaho (2005)

One of the most daring triumphs of the second wave of American indie filmmaking, My Own Private Idaho is an ultimate contemplation on growing up and selling out that embodies the outwardly contradictory directions of Van Sant’s career and, yet, is exactingly coherent. The son of a wealthy scion (Keanu Reeves) cultivates a relationship with a poor narcoleptic (River Phoenix) and an older street gangster and former lover (William Richert), both hustlers, living a kind of fantasy life that teeters on collapse. It is the central anxiety of the era, populated by the first sell-outs of ’80s counterculture, cashing their chips to the hungry post-Cold War marketplace. In this way, Amy Taubin calls the movie’s final scene, where Reeves buries his dead father and dead lover simultaneously, “a mini-allegory of the economic polarization of America that was already grotesquely evident during the Reagan–Bush I era.”

Some plug Reeves’s character as a stand-in for Van Sant himself, an upper-middle-class filmmaker whose movies slummed with the stories of impoverished outsiders. Reeves’s decision to leave the hustling world when he inherits his father’s money, in turn, seems to presage Van Sant’s own decision to take on studio scripts and compete for Oscars. Yet, unlike Reeves, who can barely stand to look at the compatriots he betrays, Van Sant would continue to pursue the same subjects undeterred.

1.  Good Will Hunting (1997)

Good Will Hunting

Two queens fall for a young lad from the other side of the tracks. Ultimately, he will leave them to be with his boys because they always do in these romances, perpetually repeating the heartbreak of otherness. In an overwritten and overhyped script by stars Damon and Ben Affleck, Van Sant found a complimentary inversion of My Own Private Idaho: Damon and Reeves’s characters both on the precipice of turning 21 and having to decide where to steer their lives. Despite how seamlessly the movie fits into the larger narratives of Van Sant’s work, Many mentions of Good Will Hunting call his directing “anonymous,” helped, perhaps, by the eventual superstardom of the movie’s two leads.

In a recent retrospective on the movie, Luke O’Neil is wary of celebrating Good Will Hunting because of the current reputations of those stars, the now-infamous Harvey Weinstein who first bought their script, and the masculine Boston street culture that it paid homage to. But that’s fine. Take that away and the movie might as well take place in Providence, Rhode Island, for all I care. Van Sant makes this movie, turning the preposterous narcissism of the writing into embers of feeling that he directs its stars to catch with their tongues. Even the movie’s ignored girlfriend (Minnie Driver) turns her role of providing the movie’s token straightness into a torch that none of the line of ignored girlfriends who followed, from Anna Paquin to Rooney Mara, could quite fill in the same way. Why do all the good ones prefer to confide in the dusty rooms of their professors? Intimately staged and perfectly cast, Robin Williams’s exuberance was toned down to the rumble of conversations between strangers at a bar, while Stellan Skarsgård’s attempt to sound more Franco-German gives his voice a strange, suggestive lilt. The movie is a masterclass on everything Van Sant uses movies to do: create intimate auras miles away from the normative world. In its exuberant final scene, where else can Will go but off-screen, toward home?

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