Charlie Kaufman: Hollywood's Brainiest Screenwriter Pleases Crowds by Refusing to Please

We open on Charlie Kaufman entering a French bistro in Los Angeles. He looks nothing like Nicolas Cage, who played Kaufman in the Kaufman-penned film Adaptation. The real Kaufman is slight, with a healthy serving of reddish-brown curls. Two vertical creases partition his eyebrows — the product, one imagines, of countless furrowings. His wardrobe is standard-issue LA screenwriter: short-sleeve Penguin button-down, tan jeans, lime-green socks. Kaufman, 50, has a reputation for shyness, but as he takes a seat in the back corner of the restaurant, he speaks directly, rapidly, forcefully.

Kaufman recently completed work on his directorial debut, Synecdoche, New York. The film, which opens in late October, is his trickiest screenplay to date, which is really saying something. Kaufman's previous mind-bending work — a roster that includes Being John Malkovich, Adaptation, and Eternal Sunshine of the Spotless Mind, for which he won an Oscar — established him as the most distinctive and admired screenwriter of his generation. With Synecdoche, Kaufman is attempting to make the jump from writer to full-on auteur. It's been five years since he started batting around ideas with his friend and sometime collaborator Spike Jonze, five long years during which he worked on this bleak story of a man's anxieties, failures, flaws, and ultimate demise. The result is a deeply personal, borderline-obsessive story of heartache and death — not the fun, f/x-enhanced-fireball kind of death that fills movie theaters, but the holy-crap-look-at-the-size-of-that-abyss kind of death that fills Sartre novels. This is not, in other words, an easy sell. And now he has to promote the thing. Which he is not very good at.

The first question is a softball — How do you feel about this film in relation to your other ones? — and the answer should be obvious: I'm prouder of this movie than any I've ever done. Everyone should see it. But Kaufman doesn't do confident. "This is a difficult period for me right now with this movie, because it's over and I want it to be over," he says. "Putting it out into the world, there's a lot of ..." He trails off, stares at a point in the middle distance for a few seconds, then continues. "It's so hard to know what I'm supposed to say. I'm participating in an article to sell this movie, but what am I supposed to say? 'It's great and I'm loving it'? It seems to be a tricky thing to sell people on, and I'm frustrated with that."

The mind of Charlie Kaufman may not be the happiest place on earth, but it is one of the most fascinating. Kaufman merges the existential despair of Beckett with the absurdist humor of Monty Python and the intellectual playfulness of a natural-born puzzle geek. (He is particularly fond of Epimenides' paradox, a classic one-sentence brain-buster: "This sentence is false.") In Malkovich's most famous scene, the eponymous actor enters a portal into his own mind. In Adaptation, a screenwriter named Charlie Kaufman writes himself into his own movie, which becomes Adaptation. And the lead character of Eternal Sunshine witnesses his memories as they are being erased, including the memory of his decision to erase his memories. Cognitive scientist Douglas Hofstadter, in his Pulitzer Prize-winning tome Gödel, Escher, Bach, refers to such regressions as Strange Loops — circular paradoxes that contain themselves. And Kaufman's Möbius scripts contain some of the strangest loops ever put to film. "I've been told that my stuff is mathematical," Kaufman says. "There's like a hidden epiphany in it for me. You think you understand something, and then another version opens up."

For anyone who doesn't mind a little gray matter with their Raisinets, Kaufman is more than a writer; he is a cultural touchstone. "It's hard not to see his influence," says Anthony Bregman, who served as producer on The Ice Storm and The Savages, as well as three of Kaufman's films, including Synecdoche. "Every submission I get is 'We have a Charlie Kaufmanesque movie for you.'"