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Mike White is less pretentious now than he was in grade school. Back then, he read – or at least carried around – Sam Shepard’s Buried Child and insisted his parents buy him a recorded version of Who’s Afraid of Virginia Woolf? He’s harbored ambitions to be a writer since the age of eight, looking for answers to life in films like Shoot the Moon, Wetherby and Kramer vs. Kramer. Given White’s self-selected syllabus, it’s not surprising his boyhood oeuvre comprised people discussing scandalous affairs over cocktails. He’s softened since then, but biting satire still makes a cameo in much of his work. As one review of The Good Girl pointed out, White “flirts with a happy ending, but it’s only a tease. There’s still blood dripping from the smiley face.” It won White Best Screenplay at the Independent Film Awards, and Jennifer Aniston her best role to date.

White grew up Pasadena, California, a town he’d later render in surprisingly dark, smart tones in a short-lived nighttime soap of the same name. He left for Wesleyan University in Connecticut, where he loved the experience and hated the weather. He returned west after graduating and got a job as a writer and producer on Dawson’s Creek and then Freaks and Geeks, a show that seemed tailor made for someone with White’s abiding love for oddballs, but he found the writer’s room a bit crowded for his taste. He started writing solo, and within a year delivered Chuck & Buck, his 2000 breakout. The New York Times called it “a strange, intense and moving film about friendship and loss, an antidote to the current epidemic of lazy nostalgia for the innocence of childhood and therefore, magically, one of the few truly grown-up movies you’re likely to see this year.” It was also White’s acting breakout (playing Buck), which the Times gave equal praise: ”Chuck & Buck as a whole exhibits the quiet sensitivity and quicksilver intelligence that infuses Mr. White’s performance.”

Chuck & Buck also exhibits another White trademark – his oddballs are not the pre-packaged loveable, goofy misfits we’re served in most comedies. Yes, they can be winning, caring and silly, but also petty, self-righteous and sometimes, straight-up creepy. His Buck is one such anti-hero; one of his best female versions is Peggy, the secretary brilliantly played by Molly Shannon in his 2007 self-penned directorial debut Year of the Dog, his third IFA Best Screenplay nomination. His best creations are born of his instinct to tread warily in a business that gives us too much of what we think we want. “There is some need to flatter the human race with the movies that we make. And if they’re not flattering, they are villains, they’re not us. And there is a part of me that thinks, ‘No, you’re that person, too.’”

The balance between comedy and the darkness that often fuels it, between cynicism and belief, is one White’s a master at striking. That deft observation is on display in the sociopolitical allegory Beatriz at Dinner; and in Brad’s Status, his exploration of comparative anxiety, which he also directed. You even see it in his screenplays, featuring his bombastic buddy Jack Black, like Orange County, School of Rock and Nacho Libre.

White’s other gift –offering up counter perspectives without becoming preachy – made HBO’s Enlightened one of the most original and acclaimed shows on television. It starred Laura Dern as Amy Jellicoe, a corporate executive who has a spiritual awakening following a major workplace meltdown. (In an irony even second-grade White would’ve considered over the top, inspiration came from his own meltdown while working on a failed show called Cracking Up.) In Amy, White gave us one of the most complex, funny and all-too-rare female leads on TV. New Republic called her “…terrible in her selfishness, in her social tone-deafness,” but also recognized her quixotic efforts to better herself and society. She’s “ridiculous, naive, but fundamentally a force for good.” As with so many groundbreaking shows, Enlightened was viewed in inverse proportion to its critical praise, but White’s okay with that. He’d rather be on the fringe of mass entertainment if it means telling original stories about quirky, misguided people who sometimes try a little too hard.

If there’s a theme to be found in White’s work, perhaps it’s our lifelong, delusional search for better, more idealized versions of ourselves. The struggle to keep who we are in line with how we want people to see us. To do good, to mess up, to start over. Why does that resonate? Because it’s truthful, relatable, hysterical, and also kind of noble.