10 Best Gus Van Sant Movies, Ranked
Director Gus Van Sant is the brains behind gems like Drugstore Cowboy, Good Will Hunting, and Milk. Since his debut in the late 1980s, he has always walked the line between the mainstream and the avant-garde. Van Sant is a filmmaker equally comfortable with unstructured character studies and award-season prestige. His best work captures a sort of haunted beauty—a quiet fascination with lost souls, wanderers, and misfits.
Whether he’s shooting grainy 16mm love letters to the Portland underground or crafting glossy biopics with A-listers, there’s a persistent sense of tenderness that runs through his work. With this in mind, this list ranks Van Sant’s must-see movies, from Mala Noche to Finding Forrester.
10
‘Mala Noche’ (1986)
Starring: Tim Streeter, Doug Cooeyate, Ray Monge, Nyla McCarthy
“I’ve got this problem. It’s a bad night.” Shot in rough, gorgeous black-and-white, Van Sant’s debut centers on Walt (Tim Streeter), a lonely gay convenience store clerk in Portland who becomes infatuated with Johnny (Doug Cooeyate), a young Mexican immigrant. Their relationship is transactional, language-barriered, and one-sided—but Walt’s obsession turns every encounter into a confession, both erotic and tragic. This is a film that’s less about plot and more about longing.
Mala Noche is offbeat and deeply moody, and it’s impressive for having been made on a budget of just $25,000 and shot on 16mm. It also demonstrates in microcosm many of the director’s stylistic hallmarks: the fascination with outcasts, the grainy texture, the dreamy pacing, the poetic voiceovers. Walt’s inner monologue provides much of the film’s reflection, laying his inner tension. Overall, the movie feels personal and unique, the work of a singular voice. Not bad for a first-time director.
9
‘Paranoid Park’ (2007)
Starring: Gabe Nevins, Taylor Momsen, Jake Miller, Daniel Liu
“I don’t know what I’m supposed to say.” Based on the novel by Blake Nelson, this murder mystery follows Alex (Gabe Nevins), a teenage skateboarder who becomes accidentally involved in the death of a security guard near Portland’s legendary skate park. But the story doesn’t unfold in a straight line—Van Sant fragments it into memories, replays, diary entries, and moments of silence.
The narrative is nonlinear, the dialogue often stilted, and the performances deeply naturalistic. In the process, Paranoid Park becomes about how it feels to carry the weight of something terrible. On the aesthetic side, Van Sant pairs dreamy visuals with an ambient soundscape, letting scenes drift in and out like half-remembered thoughts. He also uses slow-motion and hypnotic camera work for the skating sequences, making them almost seem symbolic and larger-than-life. This approach occasionally comes across as too artsy or overwrought but, in general, it works.
8
‘To Die For’ (1995)
Starring: Nicole Kidman, Matt Dillon, Joaquin Phoenix, Alison Folland
“You’re not anybody in America unless you’re on TV.” To Die For is a pitch-black satire about fame, ambition, and the obsession with being seen. Nicole Kidman leads the cast as Suzanne Stone, a local weather reporter with eyes on national stardom. To get there, she’s willing to manipulate, seduce, and even murder. When her husband (Matt Dillon) becomes an obstacle to her career, Suzanne enlists the help of a trio of impressionable teens—including a disturbingly vulnerable Joaquin Phoenix—to eliminate the problem.
From here, the movie plays like a sensational tabloid come to life, told through faux-documentary interviews, reenactments, and media snippets. It makes for a barbed statement on muckraking media and true-crime stories. This critique was arguably ahead of its time, and the dynamics it skewers have only become more ubiquitous. Much of this hinges on Kidman’s performance, which is razor-sharp, all teeth and polish, hiding the sociopathy beneath her perfect smile.
Starring: Joaquin Phoenix, Jonah Hill, Rooney Mara, Jack Black
“My whole life’s been a joke. So why shouldn’t I do stand-up?” Joaquin Phoenix leads this film (based on a memoir) as quadriplegic cartoonist John Callahan. He’s a recovering alcoholic who finds purpose and fame through his brutally honest, often offensive cartoons. After a car crash leaves him paralyzed, Callahan undergoes a reluctant transformation, helped along by his AA sponsor Donnie (a surprisingly soulful Jonah Hill) and a support group of wounded oddballs.
Don’t Worry, He Won’t Get Far on Foot has its flaws, including some tonal consistencies, some uninspired cinematography, and a few underwritten supporting characters. Nevertheless, it compensates with a funny, messy, life-affirming script and winning performances from the leads. Phoenix is defiant and magnetic, while Hill is refreshingly restrained, almost becoming the movie’s emotional anchor. For these reasons, the film manages to avoid biopic cliches (though it can definitely get a little sentimental) and becomes something more intriguing – and more affecting.
Don’t Worry He Won’t Get Far on Foot
- Release Date
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July 13, 2018
- Runtime
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114 minutes
6
‘My Own Private Idaho’ (1991)
Starring: River Phoenix, Keanu Reeves, James Russo, William Richert
“I only have sex with a guy for money… and two guys can’t love each other.” One of Van Sant’s strangest creations, My Own Private Idaho is a fusion of a road movie, a Shakespearean tragedy, and a fever dream. River Phoenix stars as Mike, a narcoleptic street hustler drifting through the Pacific Northwest in search of his long-lost mother. He’s joined by Scott (Keanu Reeves), the privileged son of a mayor slumming it in the same world, but with very different stakes. The pair undertake a slightly surreal journey from Seattle to Idaho to Italy.
My Own Private Idaho is disjointed but eclectic, pulling in visual influences from avant-garde cinema and literary ones from Shakespeare’s Henry IV. There are animated sequences and whiplash tonal shifts. But there’s authenticity and vulnerability alongside the artifice, particularly from River Phoenix. This was one of his defining performances: tender, haunted, and loaded with gravitas.
5
‘Elephant’ (2003)
Starring: Alex Frost, Eric Deulen, John Robinson, Elias McConnell
“There’s a lot of cool stuff you can do with a gun.” Loosely inspired by the Columbine massacre, the daring, divisive Elephant follows multiple students over the course of a single day, their paths quietly intersecting until the violence explodes. But there’s no traditional narrative here—no explanations, no backstories, no closure. Van Sant shoots in long, unbroken takes, trailing characters through hallways with a Steadicam like ghosts in a dream. The effect is chilling and disorienting.
The largely unknown cast improvised within Van Sant’s loosely structured framework, adding to the documentary-like feel. But rather than being a conventional psychological drama, Elephant is abstract and meditative, a snapshot of the quiet before the storm. In this regard, Van Sant was heavily inspired by the slow build and eventual conflagration of Chantal Akerman‘s Jeanne Dielman, 23 quai du Commerce, 1080 Bruxelles. He also drains the on-screen violence of any excitement or grandeur, making it dull, frank, and brutally real.
4
‘Finding Forrester’ (2000)
Starring: Sean Connery, Rob Brown, F. Murray Abraham, Anna Paquin
“You’re the man now, dog!” Finding Forrester may be Sant’s most mainstream effort, but that doesn’t mean it’s without depth or feeling. This one tells the story of Jamal Wallace (Rob Brown), a gifted teenager from the Bronx who’s offered a scholarship to an elite prep school after acing a standardized test. There, he’s dismissed for his background and accused of plagiarism—until he befriends a reclusive writer named William Forrester (Sean Connery), who becomes his reluctant mentor.
The film deploys some classic, almost Hallmark-esque beats: the misunderstood genius, the curmudgeonly teacher, the cultural clash. But it does so with surprising grace and restraint, elevated by strong lead performances. Some of the subplots fail to deliver on their promise, but the central relationship between Jamal and Forrester is handled well. In the end, it’s a solid, well-crafted story told by a talented filmmaker and cast—one that might not fully meet its own potential, but still leaves a lasting impression.
3
‘Drugstore Cowboy’ (1989)
Starring: Matt Dillon, Kelly Lynch, James Le Gros, Heather Graham
“You’re not supposed to touch anything in a graveyard.” Drugstore Cowboy was Van Sant’s first major statement—a grimy, stylish portrait of addicts drifting through 1970s Portland. Matt Dillon shines as Bob, the charismatic leader of a small crew of drugstore-robbing junkies that includes his wife Dianne (Kelly Lynch), Rick (James Le Gros), and the young Nadine (Heather Graham). Together, they travel from pharmacy to pharmacy, scoring drugs and evading the law, all while pretending they have some control over their spiraling lives.
Darkly funny, refreshingly candid, and deeply original, this movie stands out by treating its characters with endless empathy. They’re not depicted as bad people but rather as damaged people under a lot of pressure. Despite its bleak subject matter, the film is surprisingly watchable, balancing its somber tone with a dry sense of humor. Finally, on the acting front, Dillon gives one of his finest performances, capturing both Bob’s charm and self-loathing.
Drugstore Cowboy
- Release Date
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October 20, 1989
- Runtime
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102 minutes
2
‘Milk’ (2008)
Starring: Sean Penn, Emile Hirsch, Josh Brolin, James Franco
“Without hope, life is not worth living.” Milk is the most overtly political film in Van Sant’’s career, but it never feels like a lecture. Sean Penn takes center stage in this biopic as Harvey Milk, the pioneering openly gay politician to secure elected office in California. It focuses on the closing chapters of Milk’s journey, beginning with his relocation to San Francisco in the early ’70s and charting his fervent campaign for LGBTQ+ rights. Along the way, the story highlights his emergence as an influential political figure, culminating in his tragic murder by fellow city supervisor Dan White (Josh Brolin).
With Van Sant at the helm, Milk becomes a deeply personal yet urgent portrayal of Milk’s life. Rather than framing him purely as an iconic crusader, the focus lies heavily on his personal warmth and vulnerabilities, turning the movie into a character study rather than a dry history lesson. Penn delivers an astonishingly immersive performance, breathing admirable depth into the role, winning him the Best Actor Oscar.
1
‘Good Will Hunting’ (1997)
Starring: Matt Damon, Robin Williams, Ben Affleck, Minnie Driver
“You’ll have bad times, but it’ll always wake you up to the good stuff you weren’t paying attention to.” Written by Matt Damon and Ben Affleck and directed with sensitivity by Van Sant, Good Will Hunting tells the story of Will (Damon), a janitor at MIT who secretly possesses a genius-level intellect. When his violent behavior lands him in trouble, a professor arranges for Will to work with a therapist, Sean Maguire (Robin Williams), to avoid jail time.
Some moments are a little corny (like the “How you like them apples?” scene) but Good Will Hunting remains a sweet, fantastically written gem. Van Sant keeps the direction unfussy, allowing the performances and dialogue to shine. Williams, in an Oscar-winning role, is the film’s font of wisdom—his quiet monologues cut deep, revealing pain beneath the warmth. Damon, young and raw, matches him beat for beat. The dynamic between them is touching and hard-earned.
