“It’s weird talking with my back to you this whole time,” Mark Woollen says in a high, soft voice, chuckling nervously. Draped over an Aeron chair in an untucked plaid shirt and stylish two-tone sneakers, he’s attempting to edit, eat, and tell his life story all at once. It’s lunchtime, or what passes for it during a nine-to-seven summer Monday that finds him jumping from screen to screen to screen: a half-hour reprieve during which he can pick at his tricolore salad, sip his passion-fruit iced tea, and cull footage on his editing bay from a freshly cut sci-fi film set on mute. This is the first step in a months-long process of turning a two-hour movie into a two-­minute work of art.

Over the past 30 years or so, movie trailers have evolved from dutiful clip jobs prepared by the monopolistic National Screen Service to the sophisticated products of an ecosystem of competing outfits—freestanding objects of gossip, reviews, even an awards show. Most of that hype is driven by fanboys locked into cape-and-crossbow blockbusters. But Woollen is the uncontested auteur of the trailer era, a 43-year-old shaggy-haired hipster introvert who makes indelible spots for Hollywood’s highbrow one percent. Terrence Malick, David Fincher, Werner Herzog, Lars von Trier, the Coen brothers, Michel Gondry, Spike Jonze, Sofia Coppola, Alejandro González Iñárritu, Steven Soderbergh, Steve McQueen, Wes Anderson: All of them have called on Mark Woollen & Associates to turn their films into works as singular and immersive as their source material.

Or maybe, if you can believe it, even more singular, given the constraints. They are commercials, yes, but often they feel less commercial than the prestige fare they’re selling—­benefiting, like haikus, from the limitations of the form. If trailer studies were a film-school major, his spots for Schindler’s List, Traffic, The Social Network, A Serious Man, 12 Years a Slave, and Little Children would be canonical. One studio executive calls his body of work “the Criterion Collection of trailers.”

Just as movies have split into two economies — tentpoles and Oscar bait — so have their ads. One way to grab millions of itchy internet eyeballs is to crank up the punch lines and explosions even at the risk of spoiling a movie, to promise the audience more, more, more … more of the same. That is, show and tell as much of the story as you can, reassuring movie­goers they’ll get their $14 worth. The other way is to do what Woollen does: tease out what makes a film incomparable. “Mark has the difficult task and very rare talent of finding a film’s DNA in 120 seconds,” says Iñárritu, a Woollen regular (from 21 Grams to this fall’s Birdman). “Once he finds it, he translates it not by revealing its story but by expressing, in a clear but mysterious way, the film’s emotional essence.”

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Woollen’s approach varies from film to film, which is one of the reasons directors trust him so much. Where it rarely wavers is in its defiant distinction from anything you’ll see on an Imax 3-D screen. The website of the Golden Trailer Awards lists 94 outfits with all kinds of specialties. While their work is far more polished than it was in the ’80s, most of it (including some of Woollen’s) still hews to a fairly rigid structure. Act One introduces characters and situations; plot complications ensue, followed by a rapid-fire third-act montage teasing a resolution and maybe, for fun, a jokey postscript called a button. Roll titles. Their emphasis ­varies, but generally they rehash the film in a stream of expository snippets, pop-song nuggets, zippy twists, and stock sounds (like that famous Inception bwaaah!). This is trailer as compressed narrative.

Woollen’s best work — the trailers that make movie people do a double take (“He did that one too?!”) — throws much of that narrative architecture out the window, mapping not the movie’s plot but its mood. The most daring stuff usually comes in the first 30 seconds, though even the second minute’s montages don’t so much narrate as gather force. Music is always pivotal, but not because a familiar song will reliably trigger familiar feelings. One song might score an entire trailer, and if it’s recognizable, it’ll be an obscure cover version. (In his landmark Little Children spot, there was no music at all — just the sound of an oncoming train.) A Woollen classic situates you not in a story but in a world (though not “In a World …”; the voice-over of God is verboten).

Watch, for example, Woollen’s spot for David Fincher’s The Social Network. A simple piano melody scores the darkness. Pixels resolve into blurry personal photos and a blue ADD AS FRIEND button. A women’s choir starts to sing what turns out to be Radiohead’s “Creep.” Expressions of longing (for perfect bodies, perfect souls, belonging, connection) accompany Facebook screenshots of a wedding, a baby, a hospital bed — and finally (“You’re so very special”) a photo of Jesse Eisenberg as Mark Zuckerberg. Well before the minute mark, when the movie’s first scenes appear, you, in your darkened theater, are already viscerally invested in this whiny Harvard programmer and his dodgy fortune. David Fincher is the film’s director, but Woollen is the artist who made you believe in it.

That preview introduced The Social Network to the first people who saw the movie, the heads of Sony Pictures. Fincher screened it for them right before his finished cut, and they greenlit both that day. Their in-house marketers had previously mocked up their own trailer, scored to the Beastie Boys’ “Sabotage,” which made it look like “this drug-addled, debauched Hunter S. Thompson kind of thing,” says Fincher — not his movie at all. So he’d gone instead to Woollen and his boutique shop. “He made it about what connectivity really meant,” says Fincher, “and I was spellbound.”

Woollen oversees three producers and nine editors in a Santa Monica office. The ­second-floor suite, which feels like an old public school retooled as a luxury loft, was at various times the headquarters of Arnold Schwarz­enegger, Harold Ramis, a gangsta-rap label, and the painter Richard Diebenkorn.

Woollen isn’t here for the sea air and bright sun (his window shades are always down anyway) but for the creative dividends of distance. “Driving into town,” he says, “I’m just more aware of stuff — the billboards, all that noise.” The only movie poster in this office is for Jam, a documentary about aging roller-derby players, which is the only feature the boss has ever directed.

Woollen grew up mostly in the San Fernando Valley, “terribly shy” and temperamentally suited to long hours in dark rooms. Even today, he farms out the schmoozing to his producers and seems to have to remind himself to make eye contact. His negotiations with studios — and every shot must be approved — are usually done by phone and fiber-optic link.

Woollen started mixing tape in a high-school class and at home on two VCRs. He skipped college, edited some TV, and soon landed in Universal’s trailer division. At the age of 22, he cut a trailer for Schindler’s List. Like many campaigns, it was assigned to multiple competing editors. He made two draft versions — one “very layered” and the other a simple, dialogue-free montage of newsreel-style footage.

Spielberg preferred the rougher take. Suddenly possessed of industry clout, Woollen went freelance, setting up his first Avid machine in his “dank brick basement.” Even as he worked with stars, he kept his life lo-fi and his workload down to roughly ten trailers a year. Jonze remembers his “super-bachelor lifestyle. He had a bedroom that he lived in and then every other room was just editing equipment.” Woollen remembers Mike Myers looking on curiously as he cut an Austin Powers: Goldmember teaser on his dining-room table.

Long gone are the days when one trailer could sell a film. A shorter “teaser” is usually released several months out, followed, closer to release, by a couple of full-length trailers and then, post-release, maybe an online ad or two to build buzz. And there are dozens of TV spots. Trailer shops compete for ads individually, but a close relationship might result in the rare award of an entire campaign (as with Fincher’s Gone Girl), which can easily exceed $1 million in billing. But TV ads parse demographics in ways that make Woollen uncomfortable — swapping in scenes focus-grouped for stay-at-home moms, football men, or single professional females. During Monday’s morning meeting, producer Sohini Sengupta referred half-­jokingly to a set of “male-aggressive” TV ads. Woollen later calls it “the ugly black-and-white crap … The stuff I’m most passionately interested in is still the full trailer.”

Iñárittu’s Birdman is an exception; it’s his favorite campaign of the year, and he wants to worry over every piece. Starring Batman veteran Michael Keaton as a washed-up movie superhero trying to revive his career, the movie comes prepackaged in irony.

Having already finished the full-length trailers, Woollen spends almost an hour with Sengupta and an editor on the first Birdman TV commercial, which has to telegraph more in less time, and to a broader audience. He tries out different songs and takes, calls in a designer to talk kerning (font is really important to him), and orders up new samples of sounds, “just looking for other rhythms and patterns.” The editor suggests an opening voice-over. “I can’t help feeling it just undervalues the material,” says Woollen. (One of the deadliest sins in his book is “cheating” a film — either by overpromising or underselling.) “I think we could have been in that room all day,” Sengupta tells me afterward. “As I like to say, Mark will ‘frame-fuck’ things — one frame this way, one frame that way. You think it wouldn’t make a difference, but it does.”

“I’ve worked with many vendors and producers and they all say the same thing: ‘We want to be out of the box.’… and what you end up with a lot of times is something that’s just simply terrible,” says Myles Bender, who’s worked with Woollen on trailers (for Focus Features) and other projects (he co-produced Jam).* “The mark of a great artist is someone who can break the rules and create something wonderful.”

Bender’s exhibit A is Woollen’s trailer for the Coen brothers’ Job-like parable, A Serious Man. When Ethan Coen suggested, probably in jest, that Woollen make an entire trailer out of “just that part where he gets his head smashed into the chalkboard,” Woollen decided to try it. “You’re not supposed to repeat a shot” in a trailer, Bender says. “A Serious Man turned that completely on its head.”

Like Woollen’s most impressive trailers, Birdman hinges on music. Early on, editors tried scoring the trailers to David Bowie’s “Under Pressure” and “Heroes.” Both felt overfamiliar. Iñárittu suggested Gnarls Barkley’s “Crazy,” but Woollen had the same reservations. Then someone in the office found a live version Cee Lo had recorded for British TV, singing to a drum machine. It synced beautifully with the shorter “teaser.” Still, the video “wasn’t feeling special enough,” Woollen recalls. Then he remembered a long shot, 32 seconds of Keaton stalking down a hallway. It could be the perfect introduction to a movie that feels like one continuous shot. An editor ran it for only five seconds, but “I said, ‘Let’s just put the whole thing in.’ And it clicked — the feeling we’d been looking for.”

Birdman and Gone Girl are about as commercial as Woollen gets. Summer blockbusters are neither his interest nor his strong suit. Woollen helps sell what 12 Years a Slave producer Dede Gardner calls films without an “obvious headline,” crossovers with the potential to expand the mainstream. “For movies that are elliptical or episodic, you need someone who really understands tone and mood, because the story isn’t going to help you sell tickets. Mark makes something that is not commercial seem absolutely watchable.”

One of the more commercial trailers Woollen is working on has to be cut while the movie’s still being shot, with raw footage sent over daily — 70 hours and growing. “It’s just so by the numbers,” Woollen says of the script to the trailer’s producer, Jeremy Greene.

“We used to get a really rough reputation for saying ‘No’ too often,” Woollen says later—for having the temerity to turn down films like Mamma Mia (“I just thought, I don’t get this movie at all”). These days he declines work only when it isn’t important or lucrative enough to justify taking time away from current projects. There are more movies in which Woollen deals with only the studio. (He’s never even talked to some filmmakers, including the Coens.) “You want to be working with the dreamers and the risk-takers,” he says, “and you’re working sometimes with other folks that have a lot of other concerns in terms of fear and paranoia and expectations. It’s not always conducive to the most interesting work for me. But that’s why it’s a job.”

In the afternoon, Woollen supervises some tweaks to a trailer that its producer, Scott Mitsui, thought was done — until the filmmaker sent word that he’d like them to work in a favorite shot. Woollen looks a little aghast. “We’ve come up with a line where we think the footage looks good,” Woollen says, “and it’s kind of flattering to the stuff that looks a little — not, uh, as good. Maybe we’re a little pickier on it.” Pickier than the director? “There’s plenty of things I wouldn’t have put in the film. This is what happens when you look at something all day long on repeat, repeat, repeat. You see some of the flaws.” If he’s so picky, I ask later, why not make more of his own movies? “I see how difficult it is,” he says. “The company’s more stable than it’s ever been. But can I take the time to step away?”

Last month, Woollen’s wife gave birth to twin boys. After two decades making trailers, it’s an opportunity to “figure out what this next life looks like.” A month after my visit, he emailed answers to some “homework” questions: “Future — I recall you asking and me maybe not fully answering? I’ve been fortunate for many years to collaborate with some of the greatest living filmmakers. They’ve trusted me to represent their films, their work has inspired me, I have good relationships and have learned so much. I’ve spent a lot of time living in other people’s films, in worlds they’ve created, and it may soon be time where I want to create those myself.”

*This article appears in the November 3, 2014 issue of New York Magazine.

*This article has been updated to correct a quote from Myles Bender, based on an audio recording.