Gus Van Sant is certainly one of the most curious figures in contemporary American cinema.  He pioneered a very specific breed of indie filmmaking before it even had a name, but his forays into mainstream cinema have alternated between clever successes and embarrassing failures.  He gives some of the oddest interviews in Hollywood (compared to him, David Lynch is a downright pedestrian chit-chatter), and he's as dedicated to constant reinvention -- or at least refinement -- as anyone in the industry.  And his career would seem downright schizophrenic if it weren't so marked by intensely personal qualities; he's done everything from big, Oscar-baiting biopics (such as Milk, his take on the rise and demise of openly gay San Francisco politician Harvey Milk) to small, artsy, improvised tales with almost no commercial potential.  He's equally capable of having his characters spout unadulterated Shakespeare and having them say nothing at all for endless minutes of screen time, and make both choices seem perfectly natural.  He has a curiously critical eye towards his own work -- that is to say, it's not curious that he is self-critical, but rather it's curious how much he talks like a film critic; many of his longer discussions with journalists have sounded more like a well-informed film critic discussing Gus Van Sant's work than it does a director talking about himself.  His stabs at mainstream credibility have yielded decidedly mixed results; his successes have been noteworthy (see below), but his failures, especially flattened-out duds like Finding Forrester and Good Will Hunting, and an utterly pointless remake of Psycho, have been spectacular.  Through it all, he's remained one of the film industry's hardest men to figure out, but it seems no one ever tires of watching what his next move will be.  Here's five of our favorites by the Prince of Portland.

MY OWN PRIVATE IDAHO (1991)

Mala Noche was the movie that made the underground sit up and take notice of Gus Van Sant's talent; Drugstore Cowboy won over the burgeoning indie world and made him a critic's darling.  But the daring, explosively risky My Own Private Idaho was the movie that convinced me that I was seeing the work of an American genius in the making.  The story of two sad, sincere male hustlers (played by River Phoenix and Keanu Reeves), it blended elements of Shakespearean drama, class warfare, transgressive queen cinema, and pure street poetry in a way that so clearly shouldn't have worked that it's downright amazing how well it did.   Van Sant crammed the movie with real characters from his beloved Portland and made an intensely personal film that nonetheless hit everyone who saw it right where they lived.

TO DIE FOR (1995)

Gus Van Sant's first stab at commercial credibility was Even Cowgirls Get the Blues, which, despite a plethora of good intentions, was his first major dud.  In fact, its ineptness in spite of itself might be noted as a pattern that the director would follow in much of his mainstream work, if it wasn't for the existence of his follow-up film, To Die For.  Working from Buck Henry's sharpest, nastiest script in decades, Van Sant directs a movie that almost invisibly echoes some of the themes of his previous work, especially in those scenes featuring lovestruck, dimwitted local teen Joaquin Phoenix and his crew.  Van Sant rarely overreaches, and manages to let the black comedic tone of the script do its work; his greatest accomplishment is to get a truly memorable performance out of Nicole Kidman, who's better here than she would be again for some time.  

GERRY (2002)

In 2002, Van Sant was on the tail end of a bad time.  Hollywood hadn't been good to him over the previous half-decade, but to be fair, he hadn't been very good to it, either, with Good Will Hunting, Psycho and Finding Forrester gunking up his resume.  Returning to his strange interiors for another shot at indie filmmaking, he released the first of his "Death Trilogy", the underrated Gerry, and a lot of critics were ready to call it his fourth disaster in a row:  it's static to the point of tedium, its improvised dialogue (by two actors not especially beloved by highbrow reviewers) was sometimes silly and sometimes impenetrable, and it had nothing resembling a plot.  But Gerry was a quiet triumph, a movie that builds almost unnoticably and marks a return to greatness by a director who can do very much with very little.

ELEPHANT (2003)

Van Sant followed up the surprising and effective Gerry with the triumphant Elephant, the best film of 2003.  The second of his death trilogy takes an almost transcendently naturalistic look at a small high school on the day of a Columbine-style murder spree; the dialogue, again largely improvised, and the endless, unintrusive tracking shots make Elephant a brilliant contradiction:  a movie so banal that it's almost mystical.  Through the whole event, from boring ordinariness to life-shattering violence, Van Sant's particular genius is to steadfastly refuse to lead the viewers to anything resembling an explanation for the horror.  Forcing us to view everything from the eyes of those who don't understand why they have to die, Elephant reflects our own maddening desire to have random violence made explicable -- and the world's refusal to comply.

PARANOID PARK (2007)

A strangely stirring and deeply affecting film, 2007's Paranoid Park -- based largely on a successful young adult novel -- finds Gus Van Sant returning to Portland and making a key transition from the relentlessly bleak indie sensibilities of the Death Trilogy to the artsy mainstream appeal of Milk. Once again trusting an amateur cast (many of whom were recruited off of MySpace) and a good deal of improvised dialogue to carry the tone of the film, Van Sant also lays in a heavy, dark directorial touch that nails the mood of the story perfectly.  He's greatly aided in this attempt by the gorgeous cinematography by Wong Kar-Wai's cameraman, Christopher Doyle, and the Zoo-York-clad Gabe Nevins as the affectless skateboarding protagonist.  Paranoid Park is a perfect bridge between To Die For and Elephant.

Related Posts:

Screengrab Review:  Milk

Gus Van Sant and Paranoid Park: 'It's the End of a Certain Way I Was Making Films'