Photo: Fine Line Features

To put it mildly, Gus Van Sant’s three-decade feature-film career covers a lot of ground. Starting from his adopted home of Portland, Oregon, Van Sant began as a fiercely independent director, creating cult films like Drugstore Cowboy and My Own Private Idaho. He eventually moved into mainstream fare, with an enormous commercial hit (Good Will Hunting) followed by a couple disappointments (Psycho, Finding Forrester). He returned to independent cinema in the early-aughts, directing a trilogy that employed European slow-cinema techniques in uniquely American films. He later followed that up with a YA adaptation, an Oscar-winning biopic, three work-for-hire projects, and finally his latest film, the biopic Don’t Worry, He Won’t Get Far on Foot.

Needless to say, ranking Van Sant’s oeuvre presents a few challenges. For one thing, much of his feature work can’t exactly be considered “Van Sant films” in the auteurist sense, as they often sport anonymous direction and are at the mercy of truly bad scripts. Also, many of his “failures” are often more compelling than his middling entries (as a result, this list rewards ambitious misfires over bland mediocrities). Finally, his highs are very high, and his lows are disastrously low, creating an uneven list befitting an uneven body of work. Nevertheless, Van Sant is a quintessentially American director, creating stellar, personal work alongside indefensible dreck. We revisited all of it.

Imagine if Harold and Maude were written by bots and you essentially have Restless, an insufferably precious nightmare of a film about an insolent teenager, Enoch (Henry Hopper, son of Dennis), who regularly crashes funerals and falls in love with a terminally ill girl (Mia Wasikowska). You see, Enoch’s parents were killed in a car crash that put him in a coma for three months, which makes him obsessed with death, but that mostly translates to him donning a twee-forward goth wardrobe and adopting a shitty personality. It’s rare to see a film where it’s actively difficult to empathize with a kid who has experienced a lifetime’s worth of trauma, but screenwriter Jason Lew somehow pulls it off. The soundtrack (Sufjan Stevens, Bon Iver, and a really weird Beatles needle drop) desperately attempts to fill in the emotional gaps, but fails. Oh yeah, there’s also the ghost of a kamikaze pilot (Ryô Kase) who frequently shows up to play Battleship with Enoch and help him accept his parents’ death, because what Restless really needed was some quirky WWII material to give it that extra dose of phony sentiment.

16. Even Cowgirls Get the Blues (1993)

A nigh-incomprehensible mess from the jump, Van Sant’s adaptation of Tom Robbins’s cult novel desperately reaches for absurdist whimsy but can only muster arch posturing. Uma Thurman, a year before Pulp Fiction fame, isn’t equipped to carry the film as the large-thumbed Sissy Hankshaw, a hitchhiking free spirit who flies by the seat of her hippie pants. But laying all the blame at her feet feels unfair considering the script, the direction, and especially the patchwork editing job fail her miserably. (If anyone can actually recount the plot in full, they deserve a medal.) Robbins’s mystic Americana worldview is dead on arrival, despite his efforts as the film’s narrator, mostly because the freewheeling episodic structure refuses to ground it in humanity. Worst of all, Van Sant wastes a phenomenal ensemble of character actors — Lorraine Bracco, Angie Dickinson, Pat Morita, John Hurt, Keanu Reeves, Carol Kane, Udo Kier, to name a few — by giving them colorful roles to play but no direction whatsoever. Fans of k.d. lang will appreciate the soundtrack, but otherwise, Cowgirls has little to offer anyone not under the influence of peyote.

15. The Sea of Trees (2015)

The Sea of Trees mostly remains unremarkably dull for the majority of its runtime, until the last half hour sends the film careening into absurdly maudlin territory, complete with Shyamalan-lite twists. Matthew McConaughey stars as Arthur, a depressed adjunct professor who plans to kill himself in the Aokigahara forest, but just as he’s about to do the deed, he encounters a Japanese man (Ken Watanabe) who can’t find his way out. As the two trudge through the forest on a journey of survival and self-reflection, Sea of Trees flashes back to Arthur’s troubled marriage to his realtor wife (Naomi Watts) to explain how he ended up in Japan in the first place. Van Sant and cinematographer Kasper Tuxen provide the film with a fittingly eerie aesthetic, but they’re both at the mercy of Chris Sparling’s screenplay, which shifts between multiple modes until finally settling on the dumbest one imaginable. It’s difficult to explain the precise nature of The Sea of Trees’ stupidity without spoiling the ending, but suffice it to say, there’s a reason why boos rang out following its Cannes premiere.

14. Finding Forrester (2000)

Finding Forrester attempts to address the not-so-subtle racism underprivileged people of color face in elite academic environments, but any insight it contains collapses under the weight of an unconvincing central relationship and contrived narrative mechanics. Mike Rich’s screenplay follows Jamal Wallace (Rob Brown), a gifted black teenager from the Bronx recently accepted into a fancy private school, who becomes the mentee of reclusive Salinger-esque author William Forrester (Sean Connery). Forrester plays like B-grade Good Will Hunting — a wise, troubled elder and a brilliant, misunderstood youngster learning from each other — only the sentiment here feels even less earned. Brown gives a compellingly understated performance, especially for his acting debut, but he has little chemistry with Connery. Laughably histrionic moments abound: Forrester demanding Jamal hit typewriter keys with passion; Jamal facing off against his racist English teacher (F. Murray Abraham, hamming it up) by reciting the first few lines of famous poems; the entire third act. Most disappointingly, complex racial dynamics inherent in the film’s premise are sidelined for cheap villains and easy answers. What can you expect from a film that has Connery telling his 16-year-old black student, “You’re the man now, dawg”?

13. Psycho (1998)

Van Sant’s not-quite-shot-for-shot remake of Psycho functions as an interesting intertextual experiment, one that all but demands the audience have a working knowledge of the cinematic craft in Hitchcock’s original. Unlike most remakes, the film is designed to be contrasted to its predecessor, as opposed to standing on its own merits. Performances obviously pale in comparison to the original (Vince Vaughn is no Anthony Perkins and Anne Heche is no Janet Leigh), but the reproduced camera movements are similarly hollow. The film’s rhythms feel decidedly off, dragging in ways that the original never did, and the big moments never gain their own resonance. No, Psycho isn’t a good film. Yes, it’s only fascinating in the abstract. But it’s nevertheless a compelling failure. It’s a shame that major studios don’t spend $60 million on cinematic experiments anymore.

After a decade of middling projects, Van Sant returns with a biopic of John Callahan (Joaquin Phoenix), a quadriplegic cartoonist trying to overcome his severe alcoholism with the help of his AA sponsor (Jonah Hill). Chronologically disjointed but grounded in a structure inspired by the 12-step program, Don’t Worry ultimately shines more in its tossed-off moments — a joyful wheelchair ride with a new friend, Callahan’s first post-accident sexual experience, a stunningly depressing struggle with a wine cork — than the macro recovery arc. Phoenix excels at imbuing his character with physical/emotional distress that never feels too mannered, yet his characterization remains stubbornly narrow. While alcoholism was a major part of Callahan’s life, and Van Sant captures the nasty reality of his disease and the painful transition to sobriety in remarkable detail, there’s so much under-explored detail in the film’s margins, most notably his relationship with volunteer-turned-flight-attendant Annu (Rooney Mara) and his daily cartoonist grind. Van Sant’s best film since Paranoid Park remains frustratingly “on message” and shuts out other avenues of life in the process.

Promised Land sports plenty of good impulses — solid character work, charming banter, a warm tone — but the deterministic elements of John Krasinski and Matt Damon’s screenplay eventually drive the whole film to hackneyed territory. Damon stars as an energy consultant who travels to Pennsylvania farming town to convince landowners to sign over drilling rights to his employer. His efforts are impeded by an environment advocate (Krasinski) who starts a grassroots campaign to drive Damon’s company out of town. Promised Land admirably conveys the environmental dangers of fracking, albeit with the dramatic panache of a well-rehearsed stump speech, but soon the speechifying becomes overbearing and the relentless point scoring sands the edges off the drama. It’s a shame considering the cast is almost uniformly great, especially Frances McDormand and Rosemarie DeWitt (neither of whom are given enough to do). However, credit goes to the film for constructing a twist that genuinely works in the moment, even if it sort of falls apart when unpacked.

Van Sant’s Palme d’Or-winning, Columbine- and Alan Clarke–inspired drama proved divisive upon release. Was it a thoughtful, indirect examination of the frustratingly inexplicable motives behind a school shooting, or was it a shallow, exploitative recreation of a school shooting? Probably closer to the latter. Though formally immaculate (the long tracking shots of people walking down hallways really do have a hypnotically beautiful feel), it’s difficult to square away the film’s nasty structural conceit: Van Sant introduces a group of kids by their broadest personality traits and then repeatedly circles back to the moments before they’re unceremoniously murdered. Yes, Van Sant purposefully flattens their characterizations to emphasize their relationship to cultural archetypes and the education system. Yes, Van Sant’s primary interest with Elephant is to examine not just the contradictory reasons why such tragedies occur, but also our collective inability to accept such ambiguity in the face of senseless death. These are genuinely interesting ideas to consider. But that intention gets lost when you’re watching teenagers we know will get murdered perform mundane tasks up until the moment they get murdered. It may be beautifully rendered, but it’s also pretty sickening.

The Oscar-winning biopic of Harvey Milk, the first openly gay man elected to public office, is a solid entry in the annals of traditional biopics, aided by a lively Sean Penn performance and a decent portrait of community activism. Milk follows Harvey in the last eight years of his life as he transitions from San Francisco businessman to tenacious politician, determined to combat bigotry and discrimination. Screenwriter Dustin Lance Black studiously captures the major beats of his political career, as well as his loving relationship with Scott Smith (James Franco, rarely better) and his professional-cum-combative relationship with his would-be assassin Dan White (Josh Brolin). Milk hits all the marks it’s supposed to, and it does it reasonably well, but the genre’s trappings ultimately hold it back, especially in the home stretch. Individual moments stun, however, like the final candlelight vigil, and especially a late-night phone call between Milk and a disabled queer teen from the Midwest that begins as a crisis and ends as a triumph.

Van Sant’s breakout commercial hit owes more to Matt Damon and Ben Affleck’s screenplay than his anonymous direction. Nevertheless, the story of a troubled, secretly genius Bostonian (Damon) opening up and discovering his potential via his relationship with an unconventional therapist (Robin Williams) wormed its way into audiences’ hearts, eventually becoming a top ten box office hit of 1997 and netting a couple Oscars. Though the film features uniformly good performances from the entire main cast, its formulaic script, rife with subtext-explaining therapy scenes and laughably overwritten monologues, ultimately proves a liability. Sometimes the ensemble sells; other times, the disparity between the quality of the performances and the script are vast. The hangout scenes between Damon and his buddies (Ben and Casey Affleck, Cole Hauser) are stellar thanks to a relaxed energy that the rest of the film lacks, and there are a couple of capital-E Emotional scenes (Chuckie’s speech!) that work in spite of themselves. Not to be forgotten: Good Will Hunting introduced many to Elliott Smith via its soundtrack, and ultimately led to one of the finest, sparest Oscar performances to date.

7. Mala Noche (1985)

A frank, unsparing depiction of homosexual desire, Van Sant’s black-and-white debut follows the relationships between Walt (Tim Streeter) and two Mexican youths, Johnny (Doug Cooeyate) and Roberto (Ray Monge). Walt flits about Johnny and Roberto, openly thirsting after the former but also settling for the latter, while cheerfully accepting the transactional nature of their messy, ill-defined relationships. Van Sant captures Walt’s lust in stark and direct terms, both in dialogue (“My ass is sore! It’s true. I think he tried to use his cock like a weapon on me. Macho fucking prick!”) as well as swooning camera movements, particularly a crucial sex scene framed by shadows and streaks of light. Steeped in the regionalism of ’80s American indie cinema, Mala Noche functions as a portrait of Van Sant’s hometown of Portland, Oregon, but it also works wonderfully as a test reel for his blossoming aesthetic. Furthermore, his facility with actors immediately comes across, resulting in a stunning performance from Streeter in his only feature film credit. Van Sant’s debut stands as an important precursor to the New Queer Cinema movement, even if his later work doesn’t necessarily fit that mold all too well.

A truly mean-spirited, pitch-black comedy, To Die For stands out in Van Sant’s filmography solely because of how few punches it pulls and its almost complete lack of sentimentality (much of the credit goes to screenwriter Buck Henry for that). Part media satire, part crime thriller, the film follows narcissistic aspirational news anchor Suzanne Stone (Nicole Kidman, in one of her best performances) as she conspires with three troubled teenagers (Joaquin Phoenix, Casey Affleck, Alison Folland) to murder her husband (Matt Dillon). Problems arise when the film all but abandons its mockumentary conceit in the back half for a more conventional approach, but Van Sant and Henry maintain its tricky tone, which can be described as cold but not quite heartless. It doesn’t say anything new about television or its ability to shape public opinion, and yet it hardly matters when the actual story engrosses until the very end. Plus, it features stellar supporting turns by Dan Hedaya, Wayne Knight, and Illeana Douglas.

5. Last Days (2005)

In the final film of his “Death Trilogy,” Van Sant employs his experimental style to tackle the Kurt Cobain mythos. Free from the shackles of narrative convention, Van Sant captures the withdrawal-induced perma-malaise of Blake (Michael Pitt), an obvious Cobain surrogate, entirely through a formalist aesthetic. In long, unbroken takes, we watch Blake stumble in and around an enormous mansion populated by other musicians and hangers-on, playfully evade conversation and connection, and drown out the noise in his head with the noise of instruments. Similar to Elephant, many scenes are revisited from different angles, but they don’t lead us any closer to traditional understanding. Vignettes of the layabout musicians hanging out as well as the numerous “citizen” interruptions (a Yellow Pages salesman, two Mormons, a record exec) contain oblique references to the Cobain story and the myriad conspiracy theories surrounding his death, but they mostly serve to illustrate how life frequently “gets in the way.” There are times when the movie reaches too hard for profundity and cohesion, especially in the home stretch. Still, Van Sant’s empathetic eye ultimately stands out more than its flaws. Troubled minds, even fictional ones, require a gentle, contemplative hand.

4. My Own Private Idaho (1991)

Van Sant’s on-the-road romance drama stands as one of his best films, and the first to showcase a mature, semi-experimental style (watch out for the inspired sex scenes). If there’s any problem with Idaho, it’s that the explicit Henry IV scenes, featuring Portland hustlers led by a Falstaff figure (Bob Pigeon), divert attention away from the relationship between the shy, narcoleptic Mike (River Phoenix) and the confident, soon-to-be-wealthy Scott (Keanu Reeves). The Shakespeare material is fine, but literally any other scene featuring Mike and Scott perfectly captures the exposure, discomfort, and excitement of newfound love. Phoenix’s revelatory performance induces squirms thanks to its intense vulnerability while Reeves remains a steel cage, only revealing his emotions in brief flashes. It’s a pairing for the ages.

3. Drugstore Cowboy (1989)

The director’s sophomore feature acutely understands that an addict’s life is mostly repetitive. You score, get high, talk in between, take measures to ensure you can continue to score and get high, talk some more, and rinse and repeat. That might not sound like the most dramatically compelling movie premise on paper, but Drugstore Cowboy embraces the mundane, with Van Sant taking a special interest in “process” — the how’s rather than the why’s. Matt Dillon gives a tour-de-force performance as an expert conman who robs pharmacies across the Pacific Northwest with his crew (Kelly Lynch, James LeGros, Heather Graham, all pitch perfect). Their run-ins with the law (led by James Remar) are playfully combative, like schoolyard rivals, despite the obvious life-or-death stakes. Coincidences, bad luck, and cosmic ironies compound to set Dillon’s character straight, but Van Sant and co-writer Daniel Yost, working off of James Fogle’s then-unpublished autobiography, never force a judgment. Situations change, people grow apart, the cowboy life loses luster, but the mundane remains forever.

Van Sant’s expressionistic coming-of-age film acutely understands a specific, painful element of adulthood: Sometimes we have to shoulder our biggest emotional burdens alone. When 16-year-old skateboarder Alex (newcomer Gabe Nevins) accidentally kills a security guard, he doesn’t know quite what to do, but he knows that he can’t tell anyone. He destroys the evidence and keeps quiet. With no comeuppance on the horizon, Alex sublimates his shame into passivity and indifference toward his hobbies. It scans as typical moody teenage behavior, but internally, it’s a fraught nightmare. Working with an ensemble of young unknowns culled from a MySpace casting call, Van Sant crafts a fractured meditation on guilt, utilizing both his conventional and experimental tendencies to devastating effect. It’s rare that a teen film finds a way to say something new, but Paranoid Park’s sideways approach wonderfully captures the moment when an unprepared kid stumbles headfirst into the adult world.

1. Gerry (2002)

After four studio features, Van Sant returned to independent cinema with a startling aesthetic departure, a line-in-the-sand statement that signaled the director’s priorities had fundamentally shifted. Inspired by the work of Béla Tarr and Chantal Akerman, Van Sant crafted a wholly American existential two-hander about a couple of wayward slackers (Matt Damon and Casey Affleck) who embark on a hike, only to get dangerously lost in the desert. Much of the film amounts to watching the two guys (both named “Gerry,” which in the film is also slang for “fuck up”) walk aimlessly through the desert in unbroken takes as their sanity quickly circles the drain. Dialogue is sparse, and when featured, it’s either practical (e.g. strategies to climb off a rock without grievous injury) or inane (e.g. Wheel of Fortune anecdotes). Eventually, the quasi-Beckettian rhythms subside and fatigue takes its place. Van Sant eschews narrative entirely and privileges the relationship between moving bodies and the physical space they inhabit.

“But what does it mean?” you ask. The film is open enough to support many readings, but consider the most obvious, literal one: Two guys arrogant enough to think they can master a hostile, indifferent landscape leave the safety of their car and subsequently “gerry” their lives. Sometimes the universe plays the sickest jokes on those who least expect it.