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Gus Van Sant's 10 best films ranked in order of greatness

American filmmaker Gus Van Sant’s oeuvre contains a very rare combination of independent gems as well as mainstream hits like My Private Idaho and Goodwill Hunting. Recognised as one of the more popular proponents of New Queer Cinema, Van Sant has received various prestigious accolades and critical acclaim throughout his career which includes Oscar bids and the coveted Palme d’Or.

While discussing the decline of the cinematic experience, Van Sant said: “That structure has always been there, if you look for it. The idea of the next instalment of the story has been around since Oliver Twist was serialised in newspapers. James Bond was episodic. Star Wars was episodic. It was just that you saw them a year or two years apart. So I’m not saddened by that.”

Adding, “The big screen, and people going to the cinema – it became a romantic notion, but it didn’t start like that…Big screens were a corporate necessity. They were a distribution model designed to show a film to the most viewers. And now there’s a new way, because we each have a device that we hold in our hand and watch a movie on – it’s called a phone.”

On his 69th birthday, we revisit Gus Van Sant’s illustrious filmography as a celebration of his invaluable contributions to the world of cinema.

Gus Van Sant’s 10 best films:

10. Last Days (2005)

With a protagonist that is inspired by the iconic Kurt Cobain, Last Days is a poignant chronicle of the final moments of a musician’s life. The film won the Technical Grand Prize at Cannes and earned a nomination for Best Cinematography at the Independent Spirit Awards.

“They’re all about death. They form a trilogy, films that are inspired by stories that were in the papers,” the filmmaker elaborated. “Gerry was inspired by news item about two guys who got lost in the desert. Elephant was a way to look at the wave of school shootings, like Columbine that happened in the late 1990s. Last Days came out of the death of Kurt Cobain in 1994.”

9. Good Will Hunting (1997)

Definitely Van Sant’s most popular work, Good Will Hunting stars Matt Damon as a criminally neglected genius who is smarter than MIT students but works as a janitor there. Ben Affleck and Damon ended up winning an Academy Award for their screenplay.

Van Sant said: “What attracted me was the balance of the story. The thing that I’m usually sceptical about in a screenplay is the sense of story. Drugstore Cowboy was similar in that it was extremely funny, it had a very strange setting (a drug den in the ”70s), it had unique characters, amazing dialogue, intriguing ramps that the lead character, Bob, would go on. But I knew that could only last so far before the audience – me as an audience – would say, ‘Okay, so where are we going?'”

8. To Die For (1995)

Based on Joyce Maynard’s eponymous novel, To Die For features Nicole Kidman as an ambitious and manipulative woman who wants to achieve fame as a journalist. For her brilliant performance, she won a Golden Globe and earned a BAFTA nomination.

Maynard recalled: “In the summer of 1990, my three children left for two weeks to spend time with their father. I decided to use the time to write another novel. I tend to write quickly, as I had with my first book, Baby Love, and my goal was to finish this one in two weeksBut I didn’t know what it was going to be. On day one, I opened the newspaper to see that Pamela Smart had been indicted for conspiring to murder her husband.”

Adding, “I’d been transfixed by the media coverage and how she was portrayed as ‘the grieving widow.’ She was very telegenic. It fascinated me. Growing up, I’d watched a lot of TV in order to experience so-called ‘normal life.’ I wanted to be the daughter the Cleavers never had! Only later would I realise the degree to which I had been shaped by those images. So I had those two weeks and wrote To Die For in a white heat. It was published two years later in 1992.”

7. Paranoid Park (2007)

Van Sant’s 2007 drama is an essential coming-of-age film that follows the misadventures of a young skater who gets caught up in an active criminal investigation. The film received widespread critical acclaim as well as several prizes including the special 60th anniversary award at Cannes.

When Van Sant read Blake Nelson’s eponymous novel, he instantly saw the material’s potential for the big screen: “I wanted to do it with him [Nelson]. It was like a miniature young adult version of Crime and Punishment. It had all of the elements I really liked.”

6. Mala Noche (1986)

Mala Noche is now remembered as Van Sant’s significant film debut in which he conducted a cinematic adaptation of Walt Curtis’ autobiography. Shot in 16mm, Mala Noche has the ethos of New Queer Cinema firmly embedded in its framework.

Van Sant revealed: “In Mala Noche, I did do most everything. But I did it in a certain way, for instance finding a location that already has a lot of stuff in it. That already is the thing you want, so the art direction is already done. And then the casting, I did it with just a couple of friends. It was very hands-on. The lighting I did myself.”

5. Gerry (2002)

Starring Matt Damon and Casey Affleck as hiking partners with the same name of ‘Gerry’, Van Sant’s 2002 drama draws inspiration from filmmakers like Béla Tarr and Chantal Akerman as well as video games like Tomb Raider. Through the use of long takes and sparse dialogue, Van Sant constructs a memorable examination of the human condition.

The filmmaker explained: “In the case of Gerry, two friends walk through the desert, get lost, one kills the other and makes his way to a road, not realising that they were never really very far from the road in the first place. That was the one-liner, but you could read things into it. Were they inexperienced hikers? Were they intelligent? Where did they come from?”

4. Elephant (2003)

Inspired by the horribly tragic events that took place in Columbine High School in 1999, Elephant is an incisive look at the machinations of violence and carnage in a postmodern world that has been robbed of reason. It won the prestigious Palme d’Or at the Cannes Film Festival.

“I remember when [Columbine] first occurred thinking that dramatists should get in there and do something right away, as opposed to waiting 10 years. That’s against convention — whenever something intense happens, the dramatic pieces usually wait until there is more perspective,” Van Sant said.

3. Drugstore Cowboy (1989)

Gus Van Sant’s second film is also one of his best, following the lives of criminals who go around robbing drugstores in order to sustain their addictions and stay high. Drugstore Cowboy successfully translates the basic instincts that shape our motivations in the labyrinthine constructs of modernity.

Van Sant commented: “If you get anything shot, your stock goes way up. Minimum scale is like $100,000 for a script, so you can’t make less than that if you’re a Guild member. When I did Drugstore Cowboy, and got the writing fee, I just couldn’t believe it. I was afraid they’d ask me to return the money! ‘Oh, no, we’re sorry, it’s not that much.'”

2. Milk (2008)

Van Sant’s extremely important 2008 biographical drama stars Sean Penn as the inspiring figure of Harvey Milk and his struggle against the oppressions of a heteronormative society. Penn received the Best Actor prize at the Academy Awards and Milk won the Oscar for Best Original Screenplay as well.

“I was graduating high school the year Harvey Milk was killed, so I was in California, and I was certainly aware of it — it was national news, anyway,” Penn recalled. “I didn’t know anything more than this openly gay politician was murdered alongside the mayor of San Francisco.”

He added, “I think it was only a month after the Peoples Temple [Jonestown mass murder] thing had happened, which was mostly San Francisco people, so it was kind of a crazy moment in Northern California. The main problem was that normally, to tell a whole life in two hours, you want to get somebody more charismatic than the real person. And in this case, one could only aspire to that.”

1. My Own Private Idaho (1991)

Inspired by Shakespeare’s Henry IV plays, My Own Private Idaho stars River Phoenix and Keanu Reeves as a couple of young friends who are forced to navigate a world full of criminals and thugs when they embark on a spiritual quest from Idaho to Rome. The film is now widely considered to be a vastly influential achievement in the history of New Queer Cinema whose legacy is too monumental to be ignored.

Phoenix addressed the challenges he faced while portraying a narcoleptic character, “Jake was a narcoleptic in Portland who worked with me. I spent a lot of time talking to him about why narcolepsy happens. I understood it completely from the medical and scientific standpoint, though they don’t know exactly what it is. But when I was with Jake he never had a narcoleptic attack in front of me. After I’d done a few of the fits, Gus (Van Sant) said they were exactly the way Jake had them.”