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The Many Man-children of Todd Phillips

The director of ‘Old School,’ ‘The Hangover’ trilogy, and ‘War Dogs’ is obsessed with fumbling, immature young men — but that doesn’t mean he is one

Getty Images/Ringer illustration
Getty Images/Ringer illustration

Todd Phillips still remembers the first time he touched a football. He was standing in the yard of a fraternity house near the SUNY Oneonta campus in upstate New York, doing his fragile best to fit in. Skinny, deadpan, and soft-spoken, Phillips may as well have been from Antarctica. "I was getting bullied," he says. "They called me Bones."

Suddenly, the ball came toward him in a hard, perfect spiral. "Hey, Bones! Catch!" Unbelievably to him and everyone else, he did. He was 25 years old.

Phillips, a director known for Old School, The Hangover, and other anarchic comedies about boys behaving badly, grew up in middle-class Long Island with two older sisters and a mother who worked multiple jobs to support them, taking calls in a dentist’s office by day and bartending at night. His parents divorced early, a shadow darkening the edges of nearly every project he’s done. He wore dresses until he was 5 and didn’t get his first haircut until he started school.

"I was raised like a woman," he says. Remembering the football, he just couldn’t believe how hard it was.

Phillips had been on the SUNY campus making a documentary called Frat House. The movie, which was codirected with his friend Andrew Gurland and tied for the Sundance Film Festival’s Grand Jury Prize in 1998, is a bleak, unvarnished catalog of everything mothers fear when they ship their sons off to school: physical abuse, psychological degradation, cold showers and filthy basements and indigestible quantities of alcohol.

At one point, a walking tantrum nicknamed Blossom slaps Gurland in the face and brags about biting the heads off rats; at another, a brother wraps his arm around a drunk partygoer and blandly vows to have sex with her despite having no idea who she is. "You’re literally capturing an about-to-be date rape on film," Phillips tells me, half fascinated, half repulsed, a man with a movie camera watching the world unfold.

The story goes that Phillips and Gurland gained their most unfiltered access with the Alpha Tau Omega chapter at Muhlenberg College in Allentown, Pennsylvania, on two conditions: One is that the fraternity and school would be disguised. The second is that Phillips and Gurland would suffer the same rituals as the rest of the pledges. Gurland was eventually hospitalized; Phillips was locked in a dog cage and showered with beer, spit, and ash.

The conceit prefigured a convention now standard in documentary, memoir, and reality TV, wherein authors ultimately demonstrate their authority by living a subject, not just researching it. Gurland and Phillips remain polite throughout: You can tell this is the footage they wanted and more or less expected to get.

Phillips says he made Frat House out of an almost anthropological fascination about the lengths men go to in order to belong. He remembers reconvening with friends during breaks from college and listening uncomprehendingly to stories about the standard forms of harassment frat pledges go through in order to make the cut. When he was asked why they bothered, his friends explained that they wanted to build their crew, to have someone at their back. Phillips remained baffled.

"But why would you want that?"

Like many things that seem too entertaining to be true, Frat House probably wasn’t. It screened at Sundance in January 1998 and by December had become the center of a controversy, over allegations of faked scenes, that led HBO, which had given Phillips and Gurland the money to make the movie in the first place, to not air it at all.

Sheila Nevins, president of HBO Documentary Films and an executive with the company for nearly 40 years, had taken Phillips on as an intern out of NYU film school. "Todd was my brilliant wicked stepchild," she says. "Sharp as a whip. One of the ways he was sharp was he told me how great I was."

At the time, the channel was kicking around a reality series eventually called Taxicab Confessions, in which cab drivers interview their fares. "At first, it was going to be shot in the daytime," Nevins remembers. "Kids from school. People from work. A Studs Terkel kind of thing."

Eventually they shifted to night: clubgoers, drunk dates, a little boy’s dream of the big city. Watching the raw footage for an early episode, Nevins remembers one of the drivers turning around to introduce himself. It was Phillips. She was shocked. "He must’ve had a hack license or something," Nevins says. Phillips proved to have an uncanny ability to pry into people’s lurid sides. "His rides were some of the best," she says. "He asked the best questions." Nevins still has no idea how he ended up on the show.

She thought Frat House was brilliant, and was sorry it wasn’t true. "I was never angry at him. I was sorry we couldn’t use the film. I’d hoped there was a halfway between true and not-true, but there isn’t." (Phillips acknowledges that he and Gurland did "some fucked-up shit" — ingratiating themselves with the fraternity brothers by throwing parties with HBO money, getting kids drunk before inviting them to sign waivers — but otherwise maintains his innocence. The movie remains technically lost to time, salvage in the flotsam of the internet.)

Nevins adds that Phillips seems to have done pretty well for himself. "If he’d stayed in docs, he’d be living in Brooklyn in a one-bedroom apartment with two kids." Then, laughing: "I’ve never trusted an intern again."

Over the past 25 years, Phillips has made 12 feature films. Three of his first four, including Frat House, were documentaries; the rest, which include Old School and The Hangover trilogy, are features. By financial measures, he is the most successful comic director alive. By critical measures, he is one of the least. His movies have been called offensive, unfunny, and — even though he regularly travels the world for shoots when he could stay at home in Los Angeles or work in one of Canada’s facsimile cities — lazy. Nobody, including Todd Phillips, seems to consider Todd Phillips an artist, and yet his movies have exerted more ambient influence over the medium than almost anyone else working in it. He is, in a word, popular.

Warner Bros. Entertainment Inc.
Warner Bros. Entertainment Inc.

It is an unusual position for someone of Phillips’s mentality to be in. "When I was raised by my mom, it was very much, you do anything you can to stand out; you don’t want to be part of a group," Phillips says. In high school during the mid-1980s, he fell in love with Black Flag, Minor Threat, the Cramps, and Murphy’s Law, escaping the suburbs by train for the Lower East Side. The neighborhood was still a partial wasteland: crumbling buildings, urban prairie, palimpsests of graffiti, and open crime — an incubator for the kind of chaos that made Phillips feel alive.

It was here, at the bar called the Lismar Lounge, that Phillips encountered GG Allin, who later became the subject of Phillips’s first film, Hated: GG Allin & the Murder Junkies. Allin, a singer who elevated the most prurient, nihilistic sides of punk rock into something somewhere between performance art and live suicide, had been scheduled to perform a show that evening. When Phillips arrived, he noticed Allin on a barstool nonchalantly shooting heroin. "That’s GG Allin," Phillips whispered to himself as he walked past, then went downstairs and, along with the rest of the audience, waited.

He remembers peering up into the stairwell an hour later and seeing Allin teetering on the top step. Allin then took what was presumably an unscripted fall to the bottom of the stairs, knocking himself out cold. The audience descended on him like buzzards, kicking him and spitting in his face. The show was canceled. Phillips was riveted. "It was the saddest and, really, the most fucked-up thing I’d ever seen."

Phillips and I are sitting on the terrace of Soho House West Hollywood, overlooking Los Angeles, or what you can see of it through the smog. He lives nearby, but also keeps a place in New York, which he unreservedly calls "the best." He is 45, raffishly handsome. In his movies, he cameos as a character he calls Barry, covering up his own hair with a curly wig, applying a mustache, wearing sunglasses and a necklace of the Hebrew word chai — which translates to "life" in Hebrew. He started smoking when he was 15 and quits now and then. He drives a scooter and doesn’t check the helmet at the door.

It is the Friday before July Fourth and Phillips has no particular plans. "I like comedy more than I like America," he says. On the inescapable Donald Trump, whom he isn’t voting for but does appreciate in a misanthropic way: "At least he’s a fucking New Yorker. Everything he’s saying is bullshit. Him finding the Bible — Donald Trump is responsible for more women having abortions than probably every man on this fucking terrace. He has literally probably paid for more abortions of models in New York in the ’80s than all of us put together, so now he’s anti-abortion? He’s playing a role. Ted Cruz wasn’t playing a role. He was really scary. Donald Trump is a fucking New Yorker. So, worst-case scenario, you’ve got a New Yorker in the White House."

Remembering how the presence and mayhem of 1980s punk turned into the self-effacement of alternative rock and grunge, Phillips says, "What I hated about where music was headed was that everybody pretended that they hated being there. Punk rock, to me, was like pro wrestling: It was the show. You know what I mean? It wasn’t just the music, it was the show."

In hand with punk came an interest in bleak, unflinching realism. "I didn’t even like Star Wars when I was a kid," he says, an aversion that extends to swords, space, and what he taxonimizes as "anything that takes place in the air." In high school, his mom took him to see Gimme Shelter, the 1970 documentary by Charlotte Zwerin and the Maysles brothers that climaxes with the violent death of a Rolling Stones concertgoer at the hands of a Hells Angels security force that had turned on the crowd. Cold, hard, and true, it was a story Phillips believed in a language he understood.

Halfway through senior year, his mom pulled him out of school and moved them to a studio apartment on East 76th Street. Phillips’s sisters had already gone to college and Phillips had secured a full scholarship to NYU on the strength of a photography series called Suburbs, which Phillips describes as "literally 10 black-and-white photographs of kids being destructive and smoking pot and shit like that."

(The series telegraphed two of Phillips’s enduring interests: chaos and ineptitude. Remembering their halfhearted graffiti and flubbed skateboard tricks, he says, "It was kind of like documenting a group of wannabes.")

Phillips took a job at Kim’s Video & Music, a subcultural mecca that, like a lot of the places that shaped who Phillips is, has succumbed to the inevitabilities of gentrification and the internet. In a story that persists in seeming unbelievable no matter how many times he tells it, Phillips met GG Allin through Allin’s brother, a Kim’s regular named Merle, who encouraged Phillips to write Allin in prison, where he was serving time for assault with intent to do great bodily harm less than murder. (At least that’s what Phillips thinks he was in prison for at the time, but he can’t quite remember; Allin was in prison a lot.)

After what seems like a friendly and surprisingly organized phone conversation (Allin called Phillips collect), Allin agreed to let Phillips make a movie of him, which Phillips financed by selling posters designed by Allin’s friend John Wayne Gacy, a professional clown who raped and murdered 33 boys and young men between 1972 and 1978. Phillips sold the posters — autographed by Gacy from prison — in the back of Xerox-and-staple zines like Flipside and Maximum Rocknroll. Over the next two months, the project, working under the banner Skinny Nervous Guy Prod, made about $11,000, $15 at a time.

Phillips describes the business of dealing with Gacy as "fucking creepy," but as a first-time filmmaker with an estimated net worth of $100, he was willing to try just about anything. He still has an autobiographical questionnaire Gacy sent him from prison, with topics ranging from favorite color to last sexual experience. In the end, his bill was $50 and an incriminating self-portrait, which he took on the roof of his apartment at 99 Avenue B, shirtless, smoking a cigarette: Bones at Dusk.

Hated: GG Allin and the Murder Junkies premiered at NYU in early 1993, three days after Allin was released from jail. (Poetically, Allin had gone back for breaking probation by making the movie in the first place.) The movie, which is named after an Allin song called "I Live to Be Hated," spun two hours of footage into a 52-minute film, including several interviews with Allin at an NYU dorm room that had been made to look like Allin’s room at the St. Mark’s Hotel, which refused Phillips entrance on the presumption that he was coming to shoot porn.

During an early scene in which a former Allin guitarist named Chicken John describes Allin as a fraud, Allin, who was sitting in the audience, the son of religious fanatics who had legally named him Jesus Christ, began yelling at the screen as though it were real, eventually launching a 40-ounce bottle of beer through the darkness. The bottle hit a woman in the front row, and, as Phillips puts it, "she’s bleeding and the fucking screening stops and the lights come on and the cops come and GG runs out and that was the premiere of my first movie." The second and third screenings were canceled.

Phillips’s original plan was to make a trilogy of documentaries modeled after comedies he’d loved growing up: Frat House for Animal House, one on military boot camps for Stripes, and one, prophetically, about Bachelor Party. After outlining the plan during a panel at Sundance, he was approached on the street by the director Ivan Reitman and his son, Jason. "Dad," Jason said, "this is the guy I told you about." (Sheila Nevins had an analogous experience: "My son tells me his movies are the best," she says. Nearing 50, Phillips remains one of the culture’s most effective liaisons to the millennial male.)

Reitman, one of the architects of modern comedic filmmaking (as well as the producer of Animal House and director of Stripes), helped Phillips produce two movies: 2000’s Road Trip and 2003’s Old School, the latter of which repurposed Vince Vaughn as a comic actor and established Phillips as a generational wedge. (The movie still belongs to Will Ferrell, a sweet, homuncular presence who does his best work naked and, prefiguring the men of The Hangover, is inaccessible to himself without beer.)

The Hangover trilogy is not as fun as its reputation suggests. Its central characters — Alan (Zach Galifianakis), a stay-at-home man-child who orders sandwiches from his mother via intercom; Stu (Ed Helms), an apologetic dentist defined by his caution and lack of preference; Phil (Bradley Cooper), a dad; and Doug (Justin Bartha), who exists only to get lost, be kidnapped, or go to bed early — are less masters of destiny than victims of circumstance. Whatever good time they had the night before is so far removed from their normal lives and so impossible for them to remember that it might as well have happened to other people. Reckoned at a distance, the series’ plot — retracing the mystery of lost time — doubles as a detective story about how people so pent-up and unhappy manage to have fun at all. Watching it, I was tempted to ask a question I have seen on the face of my friend’s father, a Virginia farmer: Is this what has become of men?

Warner Bros. Entertainment Inc. and Legendary Pictures
Warner Bros. Entertainment Inc. and Legendary Pictures

The series gets less funny as it goes on. By The Hangover III, things have become an unmitigated bummer. Alan, an eccentric championed by his friends as a kind of mascot, becomes a 200-pound brat regulated only by psychiatry. Capers turn into chores, brushes with the underbelly — whether it’s the Vegas side streets of the series’ first movie or Bangkok nightlife in the sequel — turn into guard dogs and guns by the third, with long stretches of the characters squinting into the desert. The movie’s most complete transformation is by Ken Jeong’s Mr. Chow, who begins the series as a wild card and ends it as a sociopath, flinging himself onto the windshield of a moving car and screaming, "We’re gonna die! Finally!" Maybe this is what Cooper means when he tells me he considers Phillips an "auteur."

The series performed even better abroad than it did at home. The Hangover II (2011) made more than 56 percent of its gross outside the states; The Hangover III (2013) made 69 percent. (By comparison, foreign share for other big comedies of 2011 and 2013 — Bridesmaids, Horrible Bosses, Anchorman 2, and Grown Ups 2 — ranged from as much as about 50 percent to as little as about 25 percent.) The trilogy’s total worldwide gross is more than $1.4 billion. (Phillips says he made points on the first movie, but didn’t speak to the sequel, and declined to be quoted further about it.)

Phillips’s popularity overseas might have something to do with how unsparingly he portrays people from home. I recently attended a wedding where the best man, who was visiting from India, torpedoed a speech of remarkable tenderness with a joke about facials. As he explained to the room that he’d had to Google how to be a best man at an American wedding, I couldn’t help but think that this is exactly what someone in a Phillips movie might do: not what he wanted to but what he thought he had to, failing himself and some imaginary cowboy in the process. Reflecting on The Hangover II, Phillips says the title might as well have been Ugly Americans.

Phillips’s new movie, War Dogs, tells the story of two 20-somethings in Miami who manage to get a government contract to supply arms to U.S. troops in Afghanistan. Based on a 2011 article and subsequent book by the Rolling Stone contributor Guy Lawson, the movie is as close — however far — as Phillips has gotten to documentary in more than 15 years. (Phillips even brings back the elliptical intertitles he used in Frat House.)

On one side is David Packouz (Miles Teller), a shiftless massage therapist whose hottest prospect is selling bed sheets wholesale to nursing homes. On the other is Efraim Diveroli (Jonah Hill), a childhood friend of Packouz’s who talks him into the work. Packouz is either too innocent or too stupid to do anything but follow suit; Diveroli is the kind of person who could find a loophole in a brick wall.

On the surface, the movie bears comparisons to Adam McKay’s The Big Short, another gimlet-eyed docudrama about rigged systems and bureaucratic malfeasance made by a director who built his empire on movies in which grown men bite each other.

But like the rest of Phillips’s work, the strongest undercurrent of War Dogs is the weird, sometimes indefinable relationship between its protagonists. When Teller’s girlfriend, played by Ana de Armas, threatens to take their child and leave, Teller responds with the impersonal thoroughness of someone troubleshooting a microwave. When Hill betrays him, Teller throws a grenade paperweight — a token of Hill’s friendship and solidarity — through Hill’s window. Men might know what to do with women, but dealing with each other is hell.

Hill’s first exposure to Phillips was Old School. "I saw it the afternoon it came out and liked it so much I went back that night." (At one point, Hill actually tried to buy the rights to Lawson’s story but, as he puts it, "Todd was richer and faster.")

Like Phillips, Hill started in comedy but seems to be venturing — successfully, in his case — into more conventionally respectable territory. In certain ways, Diveroli is just a fortissimo, alpha-dog variation on The Wolf of Wall Street’s Donnie Azoff and Moneyball’s Peter Brand: smart, successful, and almost autistically obsessed with the bottom line.

For inspiration, he and Phillips looked to what Hill calls "hustler Jews from Miami," people for whom morals are the vestige of a less-efficient world. "If they could make that money selling sweaters to the army," Phillips says, "they would’ve sold sweaters. It didn’t matter." But they couldn’t make that money selling sweaters, so they sold old Chinese bullets.

Warner Bros. Entertainment Inc.
Warner Bros. Entertainment Inc.

At one point, Hill fires a warning shot in broad daylight because someone tries to stiff him on weed; at another, Hill and Teller decide to personally mule guns across the Iraqi desert on Hill’s account that they’re arms dealers, so why not deal some arms.

The movie’s ending, featuring Bradley Cooper as an arms dealer so criminal that Teller and Hill barely believe he exists, is the most compellingly unfriendly, inconclusive exchange Phillips has shot yet. What he once played for comedy — car chases, the occasional explosion — now feels like mounting evidence of an ungovernable world.

War Dogs was shot, among other places, in Romania and Morocco, on loose conditions and a tight schedule. Phillips prefers travel whenever possible. "When you shoot a movie in L.A., it’s very much like: ‘Oh, kids are going to going to bed at eight, I want to be home at seven," Phillips says. "Not that that comes to you, but you feel it."

Wide-eyed, he talks about what he describes as the "mayhem" of being abroad, the thrill of turning down unfamiliar streets and setting up where you can. "There’s something so unpredictable and sloppy about it," he says, some punk ideal of verité still turning inside him. "There aren’t rules like there are here. You don’t need cops to close streets. You just fucking do it."

Larry Sher, a cinematographer whom Phillips has worked with since The Hangover, is perennially impressed that Phillips cares about the mechanics of filmmaking at all. Making comedy, he says, "there’s this prevailing attitude that you stay out of the way of the comedy." Things are brighter, flatter, closer, and more direct in their coverage. Phillips, by contrast, uses landscapes, multiple angles, and unexpected vantages — filmic vocabulary that doesn’t necessarily make him a genius, but at least makes him considerate. A Phillips movie bothers to show you the road.

In hand with Phillips’s penchant for travel is what Sher describes as a quest to always make things leaner, smaller, more flexible, and yet more confident. "Todd and I always ask each other what we can do to make the whole machinery less," he says.

The presumption is that in doing less one frees themselves up to move more. Sher remembers a particular moment during the shooting of Phillips’s 2010 movie, Due Date, when the crew was deciding between shooting a climactic exchange between Robert Downey Jr. and Zach Galifianakis in the Grand Canyon or on green screen while stationed in New Mexico. Setting all considerations of time and convenience aside, Phillips, Sher, and six other people drove west to Arizona to scout. Overlooking the 6,000-foot pit, hot wind in his face, Phillips decided it was no decision at all. "It’s the fucking Grand Canyon," Sher says. "I know it sounds grandiose, but the fact that Galifianakis is looking at a huge pit of rocks instead of a green screen matters."

Warner Bros. Entertainment Inc. and Legendary Pictures
Warner Bros. Entertainment Inc. and Legendary Pictures

Phillips remembers the Grand Canyon shoot for different reasons: a throwaway line, one of those beats of dialogue he sensed wouldn’t work but had the Mephistophelean urge to test in screenings anyway. Standing on the ridge, having just watched Galifianakis scatter his father’s ashes to the wind, Downey says, "You know, I never asked you what your dad died of."

Galifianakis, whom Phillips describes as an actor of "beautiful innocence," turns to Downey as though answering what he feels like having for lunch and says, "Sharing needles."

The heart of The Hangover trilogy is Bradley Cooper’s character, Phil Wenneck. A married father of two burning with hedonistic visions, he is at once the group’s most responsible member and the one who pushes them hardest. He is the only character who is married before the series starts, and the only one with children. He is, by some measure, the only man in the group.

"The first time I met Todd was in L.A. when he was taking meetings with actors for The Hangover," Cooper remembers. "We ended up sitting and talking for hours." Cooper didn’t hear back for months and figured they’d cast someone else. The two have worked together several times since, both as director-actor and as coproducers on War Dogs.

Watching The Hangover, I wonder if Phillips saw in Cooper’s performance what I do: He’s the only one taking this seriously. During the opening scene of The Hangover II, Helms’s character, now on the brink of marriage, convenes Bartha and Cooper at an IHOP, where he announces that this is as far as the bachelor party will go. Cooper explodes in protest. "Drink up, everybody," he says. "Oh wait, there’s no alcohol. I forgot, we’re at a fucking IHOP."

Cooper stands up to leave; Bartha tries to talk him down. "No — no," Cooper says. "I just don’t get it. I mean, he’s getting married in Thailand. That’s great for him, but what about us?" Turning to Helms, he spits, "You’re just selfish."

Then, in the most subtle, clever transition in Phillips’s filmography, Cooper reaches down to pick up his daughter, who has been sitting quietly in her car seat: live evidence that Cooper is the only one in the group who knows the shot of what it means to stay home.

A few years ago, Phillips and his girlfriend became parents, too — a girl named Juliet. Phillips was relieved. "I wouldn’t know how to fucking play baseball with a kid or any of that. I’ve never watched a baseball game in my life."

Does being the father to a boy mean watching baseball? Maybe, maybe not. But the question still traces the shape of Phillips’s world, where some men are idiots and some are psychopaths but the broad majority are just mice fumbling around in the dark for answers about how to be, haunted by standards they didn’t invent and bound by codes they don’t understand.

"I don’t want two," Phillips says. "I’m happy with one. I’ll never have another." His reasons are reasonable: One child is a sidekick, two is an army; one is one but two may as well be four.

But there’s also the sense that another pregnancy would constitute a cosmic gamble that Phillips doesn’t want to take. For the first 16 years of his life, Phillips’s last name was Bunzl, his father’s. His mother and sisters waited for him to turn what he remembers as the legal age, at which point they all changed it together, cutting ties to Phillips’s lineage, rendering him a voluntary bastard. Reflecting on the months before his daughter was born, Phillips, who seems almost clinically bereft of self-doubt, says he had no clue what he’d do if they had a boy.

Mike Powell lives in Tucson, Arizona.

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