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Director Debuts: The 20 Best First Films of the Last 20 Years

From "Bottle Rocket" to "The Babadook," the debut feature films from the past two decades that made the biggest impact on the film world.

Running for President. Raising a child. Winning the “Hamilton” lottery. There aren’t many things that are more difficult — or more daunting — than making a feature-length film for the first time. There’s a scene in Charlie Kaufman’s “Synecdoche, New York,” itself one of the best first features ever made, in which a character’s description of life on earth doubles as an exceedingly accurate description of this soul-testing ordeal: “Everything is more complicated than you think. You only see a tenth of what is true. There are a million little strings attached to every choice you make; you can destroy your life every time you choose. But maybe you won’t know for twenty years. And you may never ever trace it to its source. And you only get one chance to play it out.”

In other words, the stakes are high and the room for error is infinite. Fortunately, however, the rewards make it all worthwhile: Directorial debuts can be (and often are) dream-killing disasters, but they can also result in some of cinema’s most thrilling discoveries.

The best of them are peerlessly exciting to watch, heralding the arrival of a bold new voice and reinvigorating our hope for the future of the movies themselves. And the 20 years since Indiewire’s inception have delivered those experiences in spades — it’s a great testament to the dynamism of the medium’s current moment that our list of the best first features of the last two decades could easily double as a list of the best films from the same span.

These movies range from indie landmarks, mainstream game-changers, formative efforts from monolithic talents, and one truly unclassifiable portrait of creation as an act of life and death. They may come from all over the world, but they all came from nowhere. These are our picks for the best first features since 1996.

Bottle Rocket

As the meticulous whimsy of Wes Anderson’s later efforts has become more refined over the last 20 years, it’s delightful to look back at his first film, “Bottle Rocket,” to remember that even then, his unique voice was undeniable. In comparison to his later films, the comedy crime caper has a distinctly rough feel, but anchored by Owen and Luke Wilson, the tale of friends who try on a life of crime is full of charms. While it ultimately bombed at the box office, it did pave the way for “Rushmore” and “The Royal Tenenbaums,” which were not just critical successes but financial as well. Anderson’s distinctive style may at times lead to mimicry or parody, but looking back at “Bottle Rocket” proves fascinating as a reminder that as a filmmaker, he’s been evolving with each new film. — Liz Shannon Miller


A throwback to when a feature debut meant a sexy, hard-boiled noir and not a coming-of-age dramedy. Starting with their first film, the Wachowski siblings showed their incredible control over the medium by skillfully weaving audiences through a twisty, tense tale of two lesbians (Jennifer Tilly and Gina Gershon) who set out to steal $2 million from the mob. Legend has it that the Wachowskis could have gotten studio backing if they were willing to change Gershon’s Corky character into a man. But holding to their original theme of not being able to judge a woman’s sexuality based on her appearance and wanting to make something original, they waited until legendary producer Dino De Laurentiis gave them $6 million and complete creative control. The Wachowski’s biggest breakthough was landing their future “Matrix” cinematographer Bill Pope, who put together a tight knit crew of technicians who helped the rookie directors execute incredibly innovative shots and find a real sense of style on a tight budget. — Chris O’Falt

Hard Eight

Critics picked up on the obvious directing chops of first-timer Paul Thomas Anderson right away with 1996 gambling noir “Hard Eight” (based on his 1993 short “Cigarettes & Coffee”), a character-driven mood piece starring Philip Baker Hall as an older sage who mentors young John C. Reilly, showing him how to play the house in Vegas. Gwyneth Paltrow (back when she was cool), big-mouth Samuel L. Jackson and PTA-regular Philip Seymour Hoffman offer strong support in the hardboiled puzzler gorgeously shot by Robert Elswit, which debuted in Un Certain Regard at Cannes. — Anne Thompson

Being John Malkovich

The first feature directed by Spike Jonze and written by Charlie Kaufman, the endlessly imaginative “Being John Malkovich” tells a far-out story with such steadfast determination and commitment to its vision that you’d swear the duo behind the scenes had been making movies for decades. John Cusack plays a lovelorn puppeteer who discovers a portal behind a cabinet in his new office that lets him enter the mind of the eponymous actor for 15 minutes. He quickly turns the trip into a business, letting others enter Malkovich’s head for $200, though it’s all to strike up a partnership and get close to the office babe Maxine (played by a never-better Catherine Keener). When she rejects him, he uses Malkovich’s body to become romantically involved with her. Oh, and he also has a wife, and all three characters need to use Malkovich for their own self-serving desires. Malkovich becomes a second skin (and the only skin) in which our characters’ intimate motivations can exist in, and the story is as much about what they do as Malkovich as it is about who they become as Malkvoich. It’s the kind of high-wire act of ambition that the pair have become synonymous with.— Zack Sharf

Boys Don’t Cry

What was so striking about Kimberly Peirce’s debut was that, thanks to its initial framework as a romance, the brutal nature of Brandon Teena’s life and death was given even more weight. Pierce did years of first-hand research into the events that led to Brandon’s death, and effectively dug into the psychology of the young men who killed him, while also making sure that the relationship between Lana and Brandon was taken seriously. Since 1999, Peirce has continued to explore unconventional material in her work, with the horrors perpetrated upon young protagonists and the resultant human damage serving as the connective thread. But it truly began with this one tragic tale.— LSM

Up next: Teenage realities and one of cinema’s transcendent swearers 

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