[4] Though most of Van Sant's other films received favorable reviews, such as Finding Forrester (2000) and Paranoid Park (2007), some of his efforts, such as the art house production Last Days (2005) and the environmental drama Promised Land (2012), have received more mixed receptions, while his adaptation of Tom Robbins's Even Cowgirls Get the Blues (1993), his 1998 remake of Alfred Hitchcock's Psycho, and The Sea of Trees (2015), were critical and commercial failures.

[11] One constant in the director's early years was his interest in visual arts (namely, painting and Super-8 filmmaking); while still in school he began making semi-autobiographical shorts costing between 30 and 50 dollars.

Van Sant's artistic leanings took him to the Rhode Island School of Design in 1970, where his introduction to various avant-garde directors inspired him to change his major from painting to cinema.

Van Sant would repeatedly focus his work on those existing on society's fringes, making his feature film directorial debut Mala Noche.

The film, which was taken from Portland street writer Walt Curtis' semi-autobiographical novella, featured some of the director's hallmarks, notably an unfulfilled romanticism, a dry sense of the absurd, and the refusal to treat homosexuality as something deserving of judgment.

Only with the success of Cowboy was Van Sant now given license to make Idaho (a film he had originally pitched that was knocked back several times because the studios deemed the script 'too risky').

New Line Cinema now gave Van Sant the green light, and he went on a mission to get the Idaho script into the hands of River Phoenix and Keanu Reeves, his preferred choice for the two young leads.

After months of struggle with agents and managers over the content of the script, Van Sant finally secured Phoenix and Reeves, who played the roles of Mike Waters and Scott Favor, respectively.

Featuring an unusually large budget (for Van Sant, at least) of $8.5 million and a large, eclectic cast including Uma Thurman, John Hurt, Keanu Reeves and a newcomer in the form of River Phoenix's younger sister Rain (at Phoenix's suggestion), the film was worked and then reworked, but the finished product nonetheless resulted in something approaching a significant disaster.

In 1997, Van Sant gained mainstream recognition and critical acclaim thanks to Good Will Hunting, which was written by Matt Damon and Ben Affleck.

It won two, including Best Screenplay for Damon and Affleck, and Best Supporting Actor Oscar for Robin Williams, who, in his acceptance speech, referred to Van Sant as "being so subtle you're almost subliminal.

"[15] Van Sant, Damon and Affleck parodied themselves and the film's success in Kevin Smith's Jay and Silent Bob Strike Back.

In 2000, Van Sant directed Finding Forrester, about a high-school student (Rob Brown) from the Bronx unlikely becoming a friend of a crusty, reclusive author (Sean Connery).

In addition to directing, he devoted considerable energy to releasing two albums and publishing a novel, Pink, which was a thinly veiled exploration of his grief over River Phoenix's death.

Approached by HBO and producer Diane Keaton to craft a fictional film based on the 1999 Columbine High School massacre, the director chose to shoot in his hometown of Portland, employing dozens of untrained, teen actors.

In 2006, Van Sant began work on Paranoid Park based on the book by Blake Nelson, about a skateboarding teenager who accidentally causes someone's death.

The film received eight Oscar nominations at the 81st Academy Awards, including Best Picture, winning two for Best Actor in a Leading Role for Sean Penn, who starred as Milk, and Best Original Screenplay for writer Dustin Lance Black.

[34][35] In December 2024, he was reported to be directing Dead Man's Wire starring Bill Skarsgard and Dacre Montgomery, and produced by Elevated Films and Balcony 9 Productions.

Van Sant went onto The Bret Easton Ellis Podcast in 2014 to discuss filmmaking, writing, film history and their collaborations that never got made (The Golden Suicides) and the one that did (The Canyons).