Dissecting the Best Gus Van Sant Movies

1. Good Will Hunting (1997)

I think this is one of the best movies ever made. So, it would be at the top of almost anyone's list. It's such a gentle movie about violence. The film was praised for its heartfelt screenplay, co-written by stars Matt Damon and Ben Affleck, and for Robin Williams' Oscar-winning supporting performance as a compassionate therapist. Van Sant's direction elevates it simple underdog story to a profound exploration of trauma and connection.

2. To Die For (1995)

An underseen classic. Legitimately just a great crime movie that contains some of the best performances I have ever seen. Buck Henry's witty screenplay and Van Sant's sharp direction create a scathing critique of the American obsession with fame. And it's also really, really funny.

3. My Own Private Idaho (1991)

River Phoenix and Keanu Reeves deliver iconic performances as two young street hustlers in Portland. Van Sant is as good a writer as he is a director, and his screenplay and direction create a haunting portrait of unrequited love and identity.

4. Drugstore Cowboy (1989)

This is one of those movies that just has a deep energy. It's a gritty and realistic look at the lives of a group of drug addicts in the Pacific Northwest. Matt Dillon gives a career-defining performance as the weird leader of the crew. It's a movie about unbearable addiction.

5. Elephant (2003)

Man, I wish this movie would stop being so relevant. It's a fictionalized account of a day in the lives of high school students that culminates in a school shooting. Van Sant employs long, tracking shots and a non-linear narrative to create a tale that just makes us want to puke and cry. The film won the Palme d'Or at the Cannes Film Festival.

6. Milk (2008)

An inspiring biopic that helped Sean Penn win an Academy Award for his portrayal of Harvey Milk, the first openly gay man to be elected to public office in California. Van Sant's direction recreates the political and social atmosphere of 1970s San Francisco, which focuses on the gay rights movement.

7. Finding Forrester (2000)

This was one of my favorite movies as a kid. I thought it was so inspiring, and I legit think it made me want to be a writer. This is a beautiful movie about the unlikely friendship between a reclusive, Pulitzer Prize-winning novelist (Sean Connery) and a gifted high school student (Rob Brown). It hits all the right notes.

8. Paranoid Park (2007)

I felt like this was a cool movie that no one ever talks about. It's a visually inventive film about a teenage skateboarder who is involved in the accidental death of a security guard. It plays with our anxieties and sense of time and justice.

9. Last Days (2005)

This movie is a fictionalized depiction of the final hours of a rock musician, heavily inspired by the life of Kurt Cobain. Michael Pitt's haunting performance creates a poignant exploration of isolation and the pressures of fame.

10. Gerry (2002)

Another movie I think is just a hidden classic, Matt Damon and Casey Affleck play two men hopelessly lost in the desert. The film strips narrative to its bare essentials; they're just wandering. It's a movie you should watch with your closest friend.

Summing It All Up 

Gus Van Sant is a really good director who explores humanity in ways I wish other people would try. He has no problem being sensitive, shooting long takes, and making movies people want to see.

Did I leave out any films you think should be on here?