How Boots Riley Infiltrated Hollywood
The cult indie rapper smuggled his radical anticapitalism into his biting new film ‘Sorry to Bother You.’
Boots Riley at Little Bistro in Oakland, Calif., in April.
By Jonah Weiner
May 22, 2018 - nytimes.com
hen Boots Riley was done writing the screenplay for his comedy, he figured he needed several name actors and a budget of a few million dollars to actually get it made. He spent decades working as a community organizer, activist and as the frontman of a leftist hip-hop group called the Coup. Riley knew a killer pitch would be necessary: “Trying to get somebody to read your script and you’re a musician?” he asked. “That’s the last person whose script you’re gonna read!”
So he honed a spiel consisting of “various levels.” Level 1 was 23 words long, and on a recent afternoon, in a coffee shop in Riley’s hometown, Oakland, Calif., he recited it to me more or less exactly as he recited it over the years to potential actors, producers, investors and advice-givers:
“It’s an absurdist dark comedy with magical realism and science fiction, inspired by the world of telemarketing. It’s called ‘Sorry to Bother You.’ ”
Riley interrupted himself: “So it’s all those things, then — telemarketing. People usually laugh right there. ‘O.K., tell me more. ...’ ”
At which point he would take them to Level 2:
“Cassius Green is a black telemarketer with self-esteem issues and existential angst who discovers a magical way to make his voice sound like it’s overdubbed by a white actor.”
Riley let that premise sink in, then moved to Level 3:
“This catapults him up the ladder of telemarketing success, to the upper echelon of telemarketers, who sell weapons of mass destruction and slave labor via cold calling. In order to do this, he has to betray his friends who are organizing a telemarketers’ union.”
Who, at this point, could resist knowing more? And who, having heard the rest — the coke-snorting billionaire bad guy, the climactic battle, the many dystopian flights of fancy — could resist helping Riley get the thing up on screen? The answer was: plenty of people. “I wasn’t getting many responses,” he recalls.
Riley has a sly grin, a slight build and a large afro. To comb it, he carries around a kitchen utensil called an angel-food-cake cutter — designed to slice delicate desserts, it does double-duty as a pick and fits comfortably in his back pocket. He furrows his brow frequently while talking to people, and if this is disconcerting at first, it turns out to be essential to his charisma, because it shows he’s actually listening to what you’re saying: Many entertainers are expert at connecting with crowds and much less adept in one-on-one interactions, but Riley takes visible pleasure in conversation.
He is also a veteran hustler, and when it looked as if “Sorry to Bother You” might never materialize, it wasn’t for lack of enterprise. At one point Riley sneaked into a private dinner at the Napa Valley Film Festival to get his script to Viggo Mortensen, with whom Riley shared an acquaintance. (Mortensen passed on participating.) He wrote to an email address belonging to the wife of Colin Firth, because the actor once approached Riley at a party rapping some Coup lyrics. (Firth said he couldn’t do the movie, either.) But Riley, who is 47, had invested too much time to give up, and there were flashes of support. The comedian David Cross, who performed alongside Riley years ago at a fund-raiser for Palestinian medical services, read the script and told Riley to count him in. Further encouragement came from Patton Oswalt, who made a similar commitment, and the author Dave Eggers, who gave the script a look and, after calling it one of the best unproduced screenplays he’d ever read, published it with McSweeney’s as a book in December 2014.
In late 2015, this gradual accumulation of boosters finally yielded funding, and more actors circled the project. Jordan Peele considered starring as Cassius for a time, then Donald Glover did, until Glover’s “Atlanta” co-star, the captivatingly droll Lakeith Stanfield, signed on as Cassius for good. Over 28 days last summer, Riley shot the movie around Oakland and Berkeley, completing a cut in time for Sundance, where Annapurna — the prestige picture house behind films by Paul Thomas Anderson, David O. Russell and Kathryn Bigelow — bought its distribution rights for seven figures. The buzz surrounding the film was excellent, if echoey: Vice called it the “most bonkers movie” at the festival; Vanity Fair called it “a bonkers social satire”; Slate called it a “feverish, bonkers satire.”
“Sorry to Bother You” comes out in wide release in July. The film is visually ingenious and funny, yet grounded by pointed arguments about the obstacles to black success in America, the power of strikes and the soul-draining predations of capitalism. A self-described communist since his teens, Riley has said he aims “to help build a mass movement that can use withholding of labor as a strategy for social change.” That credo suffuses “Sorry to Bother You” and, notwithstanding the delay in getting it made, the film’s timing could hardly be better. In Hollywood, two recent blockbusters by black directors — Peele’s horror hit “Get Out” and Ryan Coogler’s “Black Panther” — staged nuanced readings of race within fantastical scenarios. Fresh anxieties about the precariousness of work and the increasingly precarious place of the worker have, meanwhile, permeated the cultural mainstream, from mounting critiques of the so-called gig economy to the teachers’ strikes enjoying popular support nationwide to Steven Spielberg’s “Ready Player One,” a Hollywood vision of the future that features characters who become indentured servants to rapacious tech overlords.
Culture is not a substitute for direct political action, of course, but as Riley has put it, “it tills the soil and gets people ready” — and he has spent his life tilling the soil. While “Sorry to Bother You” may register as a thoroughly Trump-era artifact, its concerns have long been with him. He wrote it toward the end of Barack Obama’s first term, back when many liberals, he says, simply “turned a blind eye to real problems.” The film didn’t need to change from one president to the next, because “the system hasn’t changed.”
He knew, of course, that talking about soil and systems wouldn’t make for very enticing marketing copy. When I mentioned the avalanche of bonkerses used to describe “Sorry to Bother You” at Sundance, Riley replied: “It’s better than people going in thinking that it’s a ‘message’ movie, because no one wants to see that — I don’t want to see that! And because the truth is, every movie is a message movie. It’s just that most movies have messages that are in lock step with the status quo.”
Walking around Oakland with Boots Riley is an exercise in not getting very far very quickly. These days he shares a house with his partner — an eccentric Bay Area musician called Gabby La La — and their child. (He has three more children from earlier relationships.) But he has lived and made art all over the city, and when we sought a place to grab lunch uptown one day, the dozen or so people who stopped him to say hello included a burly white 50-something guy wearing a construction vest on a mountain bike; a black OnTrac deliveryman; a Mexican-American musician; and a Zimbabwean immigrant named Terry wearing a Tesla cap. Sometimes Riley simply smiled and made a peace sign; more often he chatted people up at length.
Riley connects with others easily, on the street and in his art — he has been writing rhymes about radical politics long enough to know how to frame ideas in punchy, compelling language. It’s a skill at the intersection of activism and art-making, which is where he sits. In high school, when he still went by his given name, Ray, he acted in student plays and danced at talent shows. (During a senior trip, where he wore a pair of brown Florsheim boots, his schoolmates gave him his nickname.) He also joined the Progressive Labor Party, at 15, and worked to unionize California farmworkers, linking up with “Mexican dudes who came to the Central Valley with the purpose of fomenting revolution, doing work in the fields — the literal fields. They had a vision that wasn’t new, but it was new to me, about how you could create a mass radical movement step by step.”
His conviction, forged in the P.L.P., is that as long as politicians are beholden to big-money “puppeteers,” the best strategy for change is to bypass the puppets and directly threaten the string-pullers’ economic interests, through work stoppages — the one radical act, perhaps, that entrenched power can’t co-opt. “It affected me because it wasn’t this vague notion of ‘change the world,’ ” he said of his time among the farmworkers. “It was, ‘Here’s a way things can happen.’ ” After that he became an advocate for Palestinian rights and a prominent member of the Occupy movement, helping Oakland residents to protest home foreclosures. In the wake of the Ferguson protests and amid the rise of Black Lives Matter, Riley, in an interview with “Democracy Now!” disputed the notion that “all you need to do is get your voice in the streets and things will change,” describing mere attempts to “shame power into action” as ineffectual. Rather, he argued that demonstrators should “combine social movements with the ability to withhold our labor” in order to “give social movements teeth.”
ne of Riley’s influences in revolutionary thinking was his father. As a San Francisco State student in the 1960s, Walter Riley was an anti-Vietnam War activist; in 1968 he drove a Muni bus around the city and helped establish a rank-and-file caucus of fellow drivers. He later volunteered as a housing-and-welfare-rights advocate in Chicago, where Boots was born, then as an auto-industry organizer in Detroit. By the time Boots was 13, they were back in Oakland, where Walter, deciding that he could do good as a civil rights and criminal-defense lawyer, went to law school and started a practice.
In 1989 Boots enrolled at San Francisco State himself, studying film. “I did shorts, but they were style exercises, very abstract, figuring it out,” he recalled. “And I was making music to go in the films.” Outside class, he joined anti-racist protests. “White supremacists said they were going to take back the Bay Area,” he told me. “They had the ‘Aryan Woodstock’ in Napa, and they’d have rallies in Union Square, with cops surrounding these Nazis.” Riley and his cohort liked to lob soda cans over the police officer’s heads, aiming for those within — a technique he pays homage to in “Sorry to Bother You.”
Riley worked part time for U.P.S., a Teamster job at which he met two aspiring rappers, Spice 1 (Robert Green Jr.), who became a prominent gangsta rapper in the ’90s, and E-roc (Eric Davis). “We’d rap in the bellies of planes we were loading up at Oakland airport,” Riley recalled. He and Davis founded the Coup with the East Bay DJ Pam the Funkstress, and when they landed a record deal, Riley quit school. (Pam died last year at 51.)
Looking back on the Coup’s first album, the brash “Kill My Landlord” (1993), Riley dismissed it as “a pamphlet on tape,” criticizing what he saw as its leaden pileup of leftist lingo. His assessment may be overly harsh, but Riley’s point was to underscore a subsequent broadening in his artistic approach that tracks through to “Sorry to Bother You”: “I moved to trying to talk to folks who don’t identify with those politics.”
He went on to fill his songs with cleverly loaded wordplay (“I slang rocks, but Palestinian style”) and set galvanizing slogans (“We got hella people, they got helicopters”) to freewheeling funk. Many of Riley’s most beloved verses unfold as vivid, frequently comic narratives. For “Fat Cats, Bigga Fish,” from 1994, he assumed the voice of a pickpocket who, posing as a waiter to hunt wealthy marks at an Oakland gala, overhears a developer pitch the mayor on a conspiracy to turn low-income housing into condos. “Ain’t no one player that could beat this lunacy,” the narrator concludes, realizing just how small-fry his own thievery is by comparison: “Ain’t no hustler on the street could do a whole community.” Even as the Coup took off on the indie circuit and landed videos on MTV and BET, Riley remained an activist. During a four-year hiatus between the group’s second and third albums, he phone-banked for nonprofits — a miserable experience that he tapped when it came time to write his movie.
One of the Coup’s best-known moments was a result of wild chance. In September 2001, the group gained notoriety for an eerily coincidental cover for its album “Party Music” — designed months earlier — in which Riley and Pam stand before a Photoshopped World Trade Center, holding up drumsticks and a bass-tuner as if they are detonators, as the towers explode behind them. (This cover, intended as a metaphorical blow against capitalism, was changed against his wishes after the Sept. 11 attacks.) Riley became an outspoken guest on shows like “Democracy Now!” and “Politically Incorrect” with Bill Maher, unflagging in what you might call his blanket bipartisan disdain for politicians. Asked by RT America in 2011, for example, about whether Barack Obama represented a “real change” from his predecessors, Riley replied, “It’s really like we just got a black manager at McDonald’s, and all the workers at McDonald’s are happy, thinking that everything’s gonna be different, but no, you still gotta get your ass in front of that cash register and you’re still gonna have to sweep and mop the floors just as hard — and you’re gonna still get paid the exact same amount, although you got a new, handsome, black manager.”
During our walk through Oakland, we passed a tiny vintage clothing store called Regina’s Door, and its owner, Regina Evans, a congenial woman in a headwrap, emerged to hug Riley. In addition to selling clothes, the shop offers financial support and “creative arts healing” to survivors of sex trafficking and provides a venue for Evans’s plays, which Riley has attended. She gave Riley a happy update on one of the women she helps support, then let him know about a new play she would be mounting soon in Berkeley. “It’s very weird and different, about a slave who kills herself and rebuilds her life with two spirits she can’t really see but knows are there,” Evans said. “Writing it, I came to a standstill and got scared: ‘I don’t think this is gonna work.’ Then I started reading your movie reviews, and everyone’s saying, ‘It’s crazy but it’s awesome.’ I said, ‘Well, Boots wrote a crazy script,’ and I started writing again.”
“That’s beautiful,” Riley said, nodding.
Much of “Sorry to Bother You” seems outlandish — on its surface. The film has a charmingly handmade ambience of hyperreality: puppetry, stop-motion animation and dozens of little offbeat details, like Cassius’ broken windshield wipers, which he must operate by yanking a piece of string. Dave Eggers sees the movie as carrying forward a tradition of “dirty surrealism, where it’s not about perfect special effects, it’s about the rawness of the subconscious. Your dreams don’t have high production values! Your nightmares are rough. Spike Jonze and Charlie Kaufman and Michel Gondry have done such incredible work in that realm, but until Boots, it’s been a while since anyone else has.”
In Riley’s hands, these fantastical elements have a clear dramatic purpose. Cassius’ ability to speak with a “white voice” (provided by David Cross) is a way to poke fun at perceptions and performances of racial identity. The film’s central villain, a company with the innocuous name of Worry Free, signs laborers to unpaid lifetime contracts in exchange for a guarantee of meals and glammed-up prison-style housing — bunk beds crammed beneath chandeliers. Worry Free’s scheme seems a touch less far-fetched when considered alongside old company-owned mining towns, Foxconn City in Shenzhen or even tech campuses with their free amenities and napping pods, meant to blur the line between work and life and extract more value from employees in the name of providing perks. Eggers, a longtime San Franciscan, said: “When I read Boots’s script, I’d just published ‘The Circle’ ” — a 2013 dystopian novel set in Silicon Valley — “and it struck me that we were both picking up on changes we’ve seen in the Bay Area. There’s this strangely sinister cast to life here sometimes, where it’s still idyllic and free and open but also there’s a sense of consolidation of power, of wealth and of control that was never part of the Bay before.”
Cassius begins the movie broke and aimless, renting a room from his uncle Sergio (Terry Crews), who is facing imminent foreclosure. When the telemarketing firm rewards Cassius’ supernatural cold-calling prowess with promotions and praise, these represent a concrete means to save Sergio’s house and the first time in Cassius’s adult life that people in power have told him he’s good at something — even if that something turns out to be shilling for weapons manufacturers and Worry Free (whose sarong-sporting chief executive is played with slick, winking malevolence by Armie Hammer). Cassius comes to see his striking co-workers and his radical artist girlfriend, Detroit (a transfixing Tessa Thompson), as impediments to the blossoming of his own excellence, but Riley and Stanfield make it compellingly tough to dismiss his motivations here as merely selling out. “Boots and I wanted to make sure he was relatable,” Stanfield told me, “a normal guy in an otherworldly situation that actually has a lot in common with real-world situations.”
Among the questions the movie raises is whether black success within capitalism is something to reflexively celebrate or whether the success of individuals who belong to an exploited class serves to ratify and consolidate — rather than thwart or ameliorate — the system doing the exploiting. Discussing this question, Riley used the example of the resolutely capitalist Jay-Z: “When people listen to Jay-Z, they’re working all day or trying to work and pay their bills, and what they hear is someone who’s free. Who doesn’t have to worry about the electricity. But all we’re taught is that those who are rich deserve to be rich because they worked harder than the rest of us or they’re smarter. And this may be true of some of those folks, but there are definitely very poor people who are very smart and work hard. It’s just that this system can only have a few people on the top. So Jay-Z is saying: ‘You can do this, too, I’m trying to give you game,’ and it ends up explaining poverty as a system of bad choices. Yes, maybe you can make better choices and be the crab that gets out of the bucket — but that’ll be at the expense of all the other crabs in the bucket.”
In the past, Riley has criticized Hollywood as abidingly reactionary in the stories it tells about black people: “All these movies — whether it’s ‘Menace II Society’ or ‘Boyz N the Hood’ — the moral is ‘Move some place else and everything’s better,’ ” he has said. “And the message is always ‘We’re destroying ourselves,’ and there’s no mention of anything systematic.” At one point, drinking coffee on stools in an uptown cafe, I brought up “Black Panther.” Riley told me that he admires Ryan Coogler and considers him “a mentor,” but his praise for that film came with an asterisk: “It was great — for a superhero movie. One of the best I’ve seen. But I have a problem with superheroes in general, because, politically, superheroes are cops. Superheroes work with the government to uphold the law. And who do the laws work for?” Riley answered this question with a smirk. “Put it like this: We all love bank robbers, because we know that in the two sides of that equation, the robbers are the ones to root for, not the banks. Only in superhero movies and the news do they try to make us think we’re against the bank robbers!”
Lakeith Stanfield and Tessa Thompson in “Sorry to Bother You.”
I asked Riley if, when shopping the film, he ever deployed his own version of a white voice. He said no, then elaborated. “Everybody feels like they’re the exception,” he went on. “There’s a story I tell, which was told to me by Tom Morello,” who was the guitarist for Rage Against the Machine, with whom Riley formed a side project several years ago. “Rage were going to shoot a music video for one of their songs, Michael Moore directed it and the idea was they were gonna show up on Wall Street and play loud in the middle of the day, and when the cops came, and when Wall Street people came and yelled at them, even if it got shut down, that would be the video. So they get there, they play the song one time. Tumbleweeds. Play it again. Nothing’s happening — a couple cops talking into their radios. They play it a third time and start hearing a rumble. ‘Are they sending SWAT in?’ And then, from around the corner, they see hundreds of people in business clothes coming closer, chanting ‘Suits! For! Rage!’ They’re fans!” (In the finished video, for the song “Sleep Now in the Fire,” a few men in trading-floor jackets rock out in the crowd.)
Transgressive gestures have a dispiriting way of being absorbed by the forces they’re intended to transgress, and so I initially took this story to illustrate how Rage Against the Machine had been revealed, in this moment, as insufficiently radical. But for Riley, it conveyed an altogether different point, one that reflected the baseline faith in other people that a lifelong activist must sustain in order to keep going: “It turns out that Rage have hundreds of fans on Wall Street who are totally into what they’re saying, and who felt like they were against the system, too, but this was just what they had to do because the system wasn’t going anywhere. And that’s what most of us feel. That we’re only doing what we’re doing because there’s no way to change things.”
One mid-April morning, Riley was overseeing the construction of a fake gate on the vast grounds of Spring Mansion, a 12,000-square-foot, 106-year-old residence in the Berkeley Hills. He squatted down and peered up through its black metal bars at the mansion, framing a shot. It was Sunday, and he and a small crew had assembled to shoot pickup footage to stitch into “Sorry to Bother You.” In the film, Spring Mansion stands in for the home of Armie Hammer’s chief executive, and at one point Cassius arrives at the gated entrance, enters a code into a keypad and walks through. This tiny but critical moment was indistinct in the current cut, because Riley ran out of time on the day of filming and had to shoot the sequence elsewhere. At test screenings, audiences consistently flagged this as confusing, and so Annapurna agreed to rent out the mansion for one more day.
Wealth in the East Bay has historically concentrated itself in the hills. Today, despite some fast-gentrifying exceptions, the general rule still holds: The flatter the land, the poorer the people living on it. Spring Mansion — named for its original owner, the mining and real estate tycoon John Hopkins Spring — was a universe away from the Oakland flats, where Riley grew up and shot most of the film. Modeled on Empress Elisabeth of Austria’s Achilleion Palace, the mansion sits ostentatiously on three acres, with balustraded terraces and a view, through palm trees, out to San Francisco Bay. The place is currently uninhabited, sitting on the market with a $7.5 million asking price, but for the next 12-odd hours, a plutocrat’s palace would become a communist’s playground.
Something about this situation seemed to make Riley a touch uneasy — or, at least, to strike him as grimly amusing. Part of his decision to shoot “Sorry to Bother You” in his hometown was his knowledge that he could call in favors, make handshake deals and save money. He enlisted friends as extras and used other friends’ artwork to decorate scenes. That spirit of community-abetted thriftiness extended all the way to the film’s Oakland premiere on April 12, where Riley wore a vintage three-piece suit that Regina Evans had given him gratis, “stuffed into a trash bag with a bunch of other suits,” he said. Riley had gravitated toward Spring Mansion in the first place because a local musician he knew once shot a video there for peanuts, and Riley figured he could finesse a similar deal. “But then line producers and location scouts insist on getting involved, and it’s out of your hands,” he said. Today’s reshoot would result in maybe five seconds of new film. Considering this, Riley chuckled and shook his head. The footage was necessary, but “if we’d been able to get to this when we were first here,” he said, “it would have taken 10 minutes instead of a whole day and, like, $100,000.”
Lakeith Stanfield flew up from Los Angeles and was driven straight to the mansion. Crew members had erected their temporary gate on the patio, marking the spot where Stanfield was to stand, consult his phone and enter the code. “I love how non-actory Keith is,” Riley told me. “He doesn’t learn all his lines until right before, so you get this sense that he’s actually figuring out what he’s going to say in the moment.”
“Hello, beautiful people,” Stanfield said, greeting the crew as he walked on set.
“777-9311,” Riley sang to him — the title of a 1982 track by the Time and, for no reason other than his love for the song, the code he wanted Stanfield to type in.
Boots’s directing style, Tessa Thompson later told me, fosters a spirit of exploration: “He did this really cool thing with me and Lakeith, where he had us do takes of scenes, but without using any words. He said, ‘I heard Spike Jonze does this, let’s try it!’ — I loved that he said he’d borrowed it from someone he respected. On the one hand he has this chutzpah and confidence, but he also has the ability to be humble and trust other people to know things that he doesn’t.”
After a few takes at the mansion, Riley broke in and altered Stanfield’s pacing a bit, to give himself options in the editing room. “Ay, check this out,” he said. It was a phrase I heard him utter several times that day — a rhetorical device that made instructions sound like shared discoveries. “This time, try starting out of frame, then walking in,” he went on. “I’ll cue you.” They shot the keypad sequence a few more times, then moved the camera around to the other side of the fence to capture Stanfield head-on.
I asked Riley whether Annapurna had given him any larger notes about the movie, expressed concerns beyond the level of logistical snags. He said no, but did mention a bit of test-screening feedback the executives passed along about the movie’s final moments, which “unsettled” some viewers. That reaction was fine by him: Riley ends the film on a note of volatility, introducing disconcerting new information in the closing seconds and then leaving this, and one of the film’s major antagonisms, unresolved.
When it came to endings, though, Riley emphasized that unresolved was not the same thing as unhappy. “It’s never all the way good or all the way bad,” he said, “as long as the fight is going on.”
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Jonah Weiner is a contributing writer for the magazine and a contributing editor at Rolling Stone. He last wrote for the magazine about Lorde.