As an artist, Gus Van Sant has tried his hand at photography, music, directing, and writing (both screenplays and novels). It turns out that he’s pretty damned talented at all of the above, but his work behind the camera has brought him the greatest degree of fame.

Gus Van Sant movies can often be relied upon to feature male actors who are uncommonly handsome (Matt Damon, Matt Dillon, River Phoenix, Keanu Reeves, etc) and present stories about individuals marginalized by society. While his willingness to tackle tough subjects (homosexuality, school shootings, and celebrity suicide) has placed him at the center of numerous controversies, his unrelenting talent has also made him a player in both traditional Hollywood cinema and the independent scene.

Though he’s suffered the occasional career misstep (Even Cowgirls Get the Blues, Psycho), Van Sant is a fearless talent who speaks to those who are so often ignored. If you’re looking for something to shake you out of your complacency, his works are a fine place to start.

• Drugstore Cowboy (1989) – Of all the Gus Van Sant movies on our list, this gritty crime drama about a drug addict (Matt Dillon) trying to go straight remains my favorite. Dillon delivers a career-defining performance as Bob Hughes, a petty criminal who robs drugstores and hospitals in order to keep his bizarre family of fellow addicts (including young Heather Graham) flush with pharmaceutical delights. Kelly Lynch is both radiant and heartbreaking as the main squeeze who’s unwilling to leave the life, and character actor James Remar is always a welcome sight. Also look for a cameo from beat author William S. Burroughs (“Naked Lunch”), himself a former heroin addict.
• My Own Private Idaho (1991) – Combining the works of William Shakespeare with the lives of male street hustlers, Van Sant delivers an edgy masterpiece of longing and love. River Phoenix pulls off the best performance of his all-too-short career, and Keanu Reeves co-stars as a privileged youth who turns tricks to pass the time. If you’re a newcomer to the independent film scene, this should be on your short list of titles to see.
• To Die For (1995) – Nicole Kidman looked her all-time best when she donned a blonde wig and seductive demeanor as an overly ambitious news reporter who plots to kill her husband (Matt Dillon) and achieve international fame. Joaquin Phoenix and Casey Affleck co-star as the witless teens pressured into homicide, and the supporting cast is rounded out by Illeana Douglas, Dan Hedaya, Kurtwood Smith, and director David Cronenberg (as a hitman). While loosely based on the real-life case of Pamela Smart, the film takes a more satirical tone and introduces a number of techniques that would later become commonplace on reality television.
• Good Will Hunting (1997) – Van Sant struck box office gold with this heartwarming story of a genius Bostonian (Matt Damon) who’s forced to undergo counseling with an unorthodox therapist (Robin Williams) in order to avoid jail time. Williams would win an Oscar for his role, as would the screenwriters (pre-fame Matt Damon and Ben Affleck). Co-starring Minnie Driver, Ben Affleck, Casey Affleck, and Stellan Skarsgard.
• Finding Forrester (2000) – While the film’s (in)famous line “You’re the man now, dog,” resulted in plenty of snickers across the Internet, the rest of this tale about a black teen (Rob Brown) who befriends a reclusive writer (Sean Connery) is packed with inspirational goodness in the vein of Good Will Hunting. Anna Paquin and F. Murray Abraham co-star, and Jeopardy host Alex Trebek shows up as himself.
• Gerry (2002) – Matt Damon and Casey Affleck star as a pair of buddies who go hiking in the desert and wind up getting lost. Okay, it may not sound like the most exciting premise, but watching these two actors and real-life friends bicker, starve, ad-lib, and eventually contemplate murdering one another is worth the price of admission. Much like the other films in Van Sant’s “Death Trilogy” (of which this was the first), the tale was inspired by a true story.
• Elephant (2003) – The middle film in Gus Van Sant’s “Death Trilogy” (along with Gerry and Last Days), this controversial work captured the Palme d’Or at Cannes, as well as plenty of flack from concerned parents. That’s because it was the first post-Columbine feature to deal with a school shooting, and the characters of Alex (Alex Frost) and Eric (Eric Duelen) are eerily similar to the perpetrators of the Colorado massacre. As with many of his indie projects, Van Sant utilized a largely amateur acting cast (with the exception of Timothy Bottoms).

• Last Days (2005) – Fans of grunge music may find this one hard to watch, as it takes a fictional look at the final day in the life of Nirvana frontman Kurt Cobain (played by Michael Pitt and referred to for legal reasons as “Blake”). Presented in a non-linear fashion with scant dialogue, it provides a glimpse into the yawning void of one man’s life. Winner of the Technical Grand Prize at Cannes, the film co-stars Lukas Haas and Asia Argento.
• Paranoid Park (2007) – Appearing on a number of critic’s top 10 lists for 2008, this dreamlike heartbreaker of a film follows a teen skateboarder (Gabe Nevins) as he deals with the aftermath of accidentally killing a security guard. Adapted from the novel by Blake Nelson, Van Sant chose to cast non-professional actors by posting a call for auditions on MySpace, proving that a talented director can coax quality performances out of almost anyone.
• Milk (2008) – Sean Penn may come off like a humorless jerk, but there’s little doubt that Madonna’s ex can act his ass off. Case in point: this Oscar-winning bio about Harvey Milk, the first openly gay individual to be elected to public office in the state of California. Milk’s rise to political power is examined in great detail, as are his various romantic entanglements (played by Diego Luna and James Franco). Josh Brolin co-stars as Dan White, a fellow city leader whose simmering hatred for counterculture types leads to a tragic conclusion. Nominated for eight Oscars–including a Best Actor win for Penn–the film was oddly banned in the nation of Samoa.

If you‘d like to experience a blend of mainstream success and arthouse bravado, go ahead and check out these 10 best Gus Van Sant movies. You’ll find satire, biographical dramas, and even a message of interracial harmony to tide you over. Strangely, there’s far less Village People music than I would’ve expected.