Van Sant’s poetic yet clear-eyed excursions through America’s seamy, skid row underbelly have yielded some of the more potent independent films of the late 1980s and early 90s.
“I guess I’m interested in sociopathic people,” he has stated, “in life and in my movies”. With art school training in painting as well as film, Van Sant worked in commercials before entering the film industry by making small personal films that played the festival circuit, notably in highbrow gay and lesbian venues. Openly gay, he has dealt unflinchingly with homosexual and other marginalized subcultures without being particularly concerned about providing positive role models. Van Sant’s first feature was “Mala Noche” (1986), a dreamy black-and-white rumination on the doomed relationship between a teen Mexican migrant worker and a liquor-store clerk. Made for about $25,000, the film won a Los Angeles Film Critics Award as the best independent/experimental film of 1987. “Drugstore Cowboy” (1989) chronicled the exploits of a rootless druggie (Matt Dillon) and his “crew” who survive by robbing West Coast pharmacies. Lyrically shot, and boasting superb performances from Dillon and co-star Kelly Lynch, the film marked Van Sant as a director of considerable promise.
Van Sant’s 1991 feature, “My Own Private Idaho”, based on his first original screenplay, starred River Phoenix as a narcoleptic male prostitute whose search for home and family takes him from Portland, OR, to such disparate locales as Idaho and Italy. Keanu Reeves plays his well-heeled companion of the streets and son of the local mayor who, like Shakespeare’s Prince Hal, goes slumming amongst the low-lifes before reclaiming his place in society. Unified by poetic visual imagery, the film combines a less than entirely successful contemporary retelling of the Bard’s “Henry IV” with a harsh, unsentimental and nonjudgmental look at the lives of hustlers.
The trades buzzed that Van Sant would make his Hollywood studio debut as the helmer of “The Mayor of Castro Street”, based on Randy Shilts’ book about San Francisco’s assassinated, openly gay city supervisor Harvey Milk. Oliver Stone was set to produce and Robin Williams reportedly wanted the lead. The project eventually fell apart due to the creative differences between Van Sant and Stone over the screenplay.
Van Sant returned to familiar territory–another indie road picture centering on an outsider (budgeted at $7.5 million), “Even Cowgirls Get the Blues” (1994). Adapted from Tom Robbins’ 1976 cult novel about a young woman whose outsized thumbs make her a formidable hitchhiker, “Cowgirls” was highly anticipated after the attention-getting success of the writer-director’s preceding two features. The film was reportedly rushed through editing to be ready for the international film festivals. After “underwhelming” audience response at the 1994 Toronto Film Festival opening night screening, “Cowgirls” was returned to the editing room for extensive recutting. (Van Sant has denied the rumors that reshooting was required.) Nonetheless, the final product was deemed a tedious bore, top heavy with would-be quirky characters. It fizzled with both critics and audiences.
The debacle of “Even Cowgirls Get the Blues” could have derailed Van Sant’s career had he not already committed to helming “To Die For” (1995), his first major studio project, before the release of “Cowgirls”. The medium budget satire also marked the first time Van Sant directed a film without receiving a screenplay credit. Scripted by Hollywood veteran Buck Henry, “To Die For” was inspired by the true story of a high-school teacher who seduced her teenage lover into murdering her husband. A modest commercial success, the film was a critical hit for everyone involved, particularly its star Nicole Kidman who portrayed the media-obsessed careerist who romances Joaquin Phoenix into murdering Matt Dillon. Some demurred from the consensus, dismissing the critique of American media as facile and Kidman’s characterization as misogynistic. However, most were impressed by Van Sant’s empathetic handling of the alienated teen characters.
That same year, Van Sant served as executive producer on one of the more controversial films of 1995–Larry Clark’s “Kids”, a ‘verite’-styled drama about the sex and drug habits of a group of middle-class Manhattan teens. Some found the work profound, while others found it profoundly troubling for its “exploitive” use of young actors (though the filmmakers maintain that all actors shown simulating drug-taking and copulation were at least 18). Van Sant’s favored cinematographer Eric Edwards (”Mala Noche”, “Drugstore Cowboy”, “My Own Private Idaho”) lensed the visually striking feature.
As a follow-up, Van Sant returned to the director’s chair to guide “Good Will Hunting” (1997), about an underachiever (Matt Damon) on the road to self-destruction who finds unlikely aid from several people, including a therapist (Robin Williams) and his best friend (Ben Affleck). Written by Damon and Affleck, the film is well-crafted, but somewhat predictable. Van Sant’s sure-handed direction and authentic sense of place (it is set in Cambridge, MA) overcome whatever deficiencies and he elicited strong performances from the cast. While “Good Will Hunting” might seem an unlikely choice for the director, its themes of outsiders struggling to connect to the mainstream place it squarely in his oeuvre. The feature’s success moved Van Sant toward mainstream Hollywood.
Since 1984, Van Sant has been making an annual, autobiographical short film that he ultimately plans to assemble into a cinematic diary; Van Sant also paints, plays guitar and writes for his own Portland rock band, “Destroy All Blondes.”