Radical As Ever, Boots Riley Takes On the Tech Boom

When I meet Boots Riley at an art studio in Downtown Oakland, he’s wearing a little bit of everything. On top, a checkered blazer over a cardigan and a white dress shirt open to the fourth button; below, salmon pants and bright white sneakers. His outfit is accented by a pocket square, and by his unruly signature mutton chops and mustache. Trying too hard is frowned upon in Oakland, and Riley was brought up in The Town, so while the first-time filmmaker may be making Hollywood inroads, his mismatched mise-en-scene is pure Bay Area: an overburdened key ring, a wallet straining with business cards and transit passes.

We walk to a café without Wi-Fi and with two distinct styles of iced coffee, a few blocks from what has emerged as the symbol of Oakland's recent tech-fueled gentrification: a block-sized building that Uber paid $123.5 million for in 2015, only to sell two years later without ever moving in. The virtual wealth infusion altered its surroundings, spurring rent hikes, evictions, and development aplenty. Nearby, three nascent high-rises stretch their naked girders upward, though they may be hard to fill without the promised influx of workers. According to a California Housing Partnership Corporation report, an Oakland resident needs to earn almost $50/hour to afford median rent in the city today. It’s right here, right at this unstable moment, that Riley has set his film, a surrealist comedy about his changing hometown.

Sorry to Bother You, which opens in multiple cities July 6, stars Atlanta’s Lakeith Stanfield as Cassius, a young man who takes a job at a telemarketing firm to help save his uncle’s (Terry Crews) house from being repossessed. He quickly becomes a star at the company after his co-worker, played by a sage-like Danny Glover, teaches him to use his “white voice” to make sales. (Stanfield’s phone voice comes courtesy of David Cross; that of another “power caller” is voiced by Patton Oswalt).

While Cassius rises through the ranks and learns the telemarketing firm's true purpose, tension comes by way of a union push on the company’s ground floor, spurred by Cassius’s best friend (Jermaine Fowler), his girlfriend, Detroit (Tessa Thompson), and an organizer (Steven Yeun) who arrives with a plan. Cassius is forced to decide between saving his uncle’s home and supporting his fellow workers. Riley knows it’s not a new story—“usually it's a dance-off to save the house,” he says, grinning—but the rapper/activist’s first feature is clearly a Boots Riley Production: a fast-paced and radical assault on both capitalism and polite society.

Riley was born in Chicago and then his family moved to Detroit for a spell, but Boots arrived in Oakland at the age of six and came to embody the city. His house was always political—his parents met during the San Francisco State student strike in 1968 and his father Walter’s activism infected his son. Boots participated in his first strike, at a cannery in Watsonville, when he was 14. He joined the Progressive Labor Party the next year.

Riley was already a radical when his rap group the Coup put out their first album, Kill My Landlord, in 1993. That was the same year that Snoop Dogg released Doggystyle, A Tribe Called Quest delivered Midnight Marauders, and Wu-Tang dropped Enter the Wu-Tang (36 Chambers). The Coup’s sound matched the time, with Riley’s flow bathed in frenetic funk—references to Ghanian revolutionaries over samples of a late-60s jazz trio. It was accessible revolution; beats, rhymes, and labor strife.

Over the next two decades, The Coup put out five more albums, with ballads about pimps named Jesus and musings on ways to murder high-powered execs. And against all odds, Riley made it: his anti-capitalist rap broke through. Riley never shied away from his newfound platform, speaking out against the war in Iraq, doing regular guest spots on Bill Maher’s Politically Incorrect, and becoming a face of the Occupy movement. He offended the right people—Fox News commentator Michelle Malkin called his song “5 Million Ways to Kill a CEO” un-American—and remained unflinching. And he never left Oakland.

By 2012, Riley, then 41, started shopping a screenplay for a radical comedy about unions, displacement and the insidious effects of capitalism. It was a quixotic pitch, but Riley was used to hustling. As a young musician, he already understood how to press connections and guerilla market—he’d give his tapes to the guys in the neighborhood with the best sound systems in their cars and have them bump it down the block.

He knew his screenplay was like a Coup album on a page: strange and energetic and funny, even as it took on weighty issues. “The Coup’s music is not just like, ‘I’m angry, fuck that, fuck this,’ you know?” Riley says. “I chose to do art in the way I always do it, which is with all the crazy contradictions of life in there.”

In 2014, Riley ran into the author Dave Eggers by his pirate store at 826 Valencia. Riley had spent two years unsuccessfully pitching the screenplay; he asked Eggers if he’d give it a read. Eggers says he was wary at first, because he was a fan of the Coup and didn’t want the awkwardness of disliking Riley’s creation. “But within two pages, I knew Boots had lightning in a bottle,” Eggers says. “It was hilarious, and very brave, and had just enough insanity to be totally relevant to our time.” Eggers published the screenplay as a special issue of his literary magazine, McSweeney’s Quarterly Concern.

I first met Riley right around that time, when I spotted him seated alone at Arbor Café, another crowded and art-centric coffee shop in Oakland. His was an enviable celebrity, anonymous to most. (A woman walked up to say hello during our latest meeting, but quickly revealed that Riley knew her mom and dad.) When I went over to his table, he was warm and asked me what I did for work; when I told him I was a journalist, he quickly and unabashedly brought up his new screenplay. Riley was undamped by the resistance he'd met with—he felt certain that Eggers co-signing the project would give the film momentum. He was right; soon after, Riley received a grant from the San Francisco Film Society and was invited to Sundance’s Screenwriters Lab. In 2016, producers got on board—including Forest Whitaker’s company, Significant Productions—and then things began to change.

Nina Yang Bongiovi, who runs Significant alongside Whitaker, immediately started pressing investors and agents hard on Riley’s behalf. The indie studio had made its name by championing another Oakland filmmaker’s first feature: Ryan Coogler’s Sundance-winner Fruitvale Station. Bongiovi and Whitaker had struggled to find funding for that film, with investors admitting that they did not trust a first-time black director. Bongiovi was surprised and annoyed by the response. “I thought, ‘Man, I got Forest Whitaker, everybody’s gonna fund this film!’” she says. “But, no, it doesn’t work that way.”

And though the success of Fruitvale Station bolstered Significant’s track record and made it easier to get their newest film by a first-time black director funded, Bongiovi says they still ran into familiar wariness. And Riley was not just a first-time black director; he was a rapper. He was also an outspoken anti-capitalist who ran a "punk/funk/communist revolution band," was front-and-center for Occupy and for Palestinian liberation, and had a hit track called “The Guillotine.” A risk-averse industry was nervous about the project, even with Forest Whitaker’s blessing. But eventually, the roles were filled and the funding came through.

Meanwhile, Riley still needed to prepare to shoot his first feature. He had studied film two and a half decades before at San Francisco State, but knew he had to relearn everything. He says he “just went out and snatched mentors” wherever he could find them. Guillermo del Toro told Riley he was too busy but then answered every one of the first-time filmmaker’s emails—eventually, he helped find the effects company for the film. David Gordon Green invited Riley to shadow him as he shot his Amazon show Red Oaks; Eggers connected him with Spike Jonze for a “three-hour master class;” Catherine Hardwicke put him up when he came down to LA.

All the while, Riley read every interview on AFI.com, paid for seminars with Judith Weston and Bruce A. Block, and incessantly watched films, like French director Leos Carax’s Holy Motors and Paul Schrader’s Mishima: A Life in Four Chapters. He was searching for expertise, but also for the ways that masters managed to explore and to play behind the camera. He wanted to tell a radical story that millions of people would buy a ticket to see—just as in his music, he knew the tone would be essential.

Riley’s satire is never wider than in its treatment of WorryFree, the tech giant run by the movie's big bad: CEO Steve Lift, played by a caftan-wearing Armie Hammer. WorryFree is omnipresent around Riley’s reality-adjacent vision of Oakland—throughout the movie, billboards and news segments and infomercials tout the perks of signing a lifetime contract with the company for what amounts to indentured servitude (Dorm living! Free housing! Three meals a day!).

Hammer, of the Ken Doll looks and multimillion-dollar inherited oil fortune, perfectly embodies the film’s antagonist. His villain is Mark Zuckerberg, only with swagger; Jeff Bezos with fantastic hair. He wears the outfit of the Wokebro, while filling the age-old role of the industrialist. Riley built him as warning against trusting the smiling billionaire who makes you call him by his first name. "This idea of 'cool capitalism' is still capitalism,” Riley says. “It doesn't matter if Elon Musk quotes Nas.”

The satire serves a deeper purpose than cheap laughs. WorryFree reads as cartoonish, but the heart of its villainy—anti-unionism in favor of efficiency, selling regardless of the client’s morality, innovating without weighing the costs—is strikingly recognizable. If this were a dry argument about the threat of Big Tech, the audience would check out. Instead, Riley has slipped his radicalism into a lively, digestible, and a bit devious package. It was a trademark of his music, and he manages to translate it into his first film.

Riley speaks in essays, leaning heavily on history to support his arguments; during a discussion on fighting capitalism from within, he weaves in references to southern Mexican worker uprisings and Serbian filmmakers. He’s not just a student of the movement, though; his earlier career has given him the advantage of a birds’ eye view.

The Coup hit its stride during the era of Pets.com and endless IPOs, and Riley brushed up against the untethered infusion of cash, taking money from a short-lived startup called Niche Music for the group’s 2001 album Party Music (the album’s cover art, prepared in June 2001, infamously featured Riley and Coup DJ Pam the Funkstress blowing up the World Trade Center). The company flew its workers to London to watch the Coup play—it had a full TV studio in its office, though most people had not yet even thought of streaming video online.

“During the first tech boom, I was publicly saying it was bullshit. And I was looked at as crazy,” Riley says. “I think there's a little bit of bullshitting going on right now too.”

In the six years since the screenplay was written, the public’s view of Silicon Valley has begun to catch up with his. But while Sorry to Bother You’s antagonist may be Hammer’s Lift, Riley is less concerned with villains than systems. “Steve Lift could be Henry Ford,” Riley says. “The tech world is not a new phenomenon; it's a new era.”

And that new era has brought with it dystopian fallout usually reserved for satire. When Riley conceived of his script in 2012, he wrote in establishing shots of tent cities as Cassius drives to his first day of work. Initially, he’d imagined the construction of the homeless encampments as a cost, but the ones in the film were all too easy to find in Oakland in 2017. Bongiovi was shocked to return to Oakland five years after Fruitvale Station; the city felt unrecognizable from the one she’d seen beside Coogler.

But while the foregrounded action is distorted to the point of farce, the satire never tips over the edge—largely because Riley's characters feel so lived-in. Steve Yuen’s Squeeze is part Boots, part a local labor activist he knows; Cassius is Riley without exposure to movement work as a kid. Most impressively, Tessa Thompson’s Detroit, who steals every scene she’s in, reads as three-dimensional, instead of being flattened into an eccentric muse. “I wrote all the characters as if they were me,” Riley says. “It was like playing chess with myself.”

The board he plays his characters upon is not large—in the movie, Cassius’s uncle’s house is just five miles from the luxury apartment he moves into, and a different five miles from Lift’s mansion in the hills. Housing and labor are front and center in Sorry to Bother You, because that’s the story of the Bay Area in 2018. But this is an Oakland film, fully recognizable and full of contradictions. San Francisco never even comes up.

I'm in the Central Valley when my cell phone finally rings. I pull off Highway 5 a bit past Lost Hills, California, beside some piles of sand and stray trash, and four dead fish, uncooked and partly eaten. I’m 90 miles from the ocean, and it’s 95 degrees and dry—the scene is incongruous in a way that seems fitting. I pick up and Danny Glover, who participated in the 1968 San Francisco State strike alongside Boots’ parents, is on the line.

Glover has spent most of his 71 years in San Francisco and has an even clearer view of the changing region than Riley. He lived through the forced migration of black San Franciscans from the city's Fillmore District via urban renewal a half-century ago. He saw the manic development and investment of the first tech boom and the subsequent crash. And yet, for him, this last decade still feels strange, if familiar. He’s struck by the alienating effects of innovation—by what he flatly calls “the absurdity of it all.”

Glover’s pride in Boots rings through, even with shoddy reception on the side of the road. He’s watched his friend's son become a prominent activist, and closely tracked his music industry rise. And Glover’s seen Riley stay radical, just like him, the film industry staple who managed to be both Roger Murtaugh and the one who called George W. Bush racist well before Kanye West. When Glover first read Riley’s script, it took him a moment to process it. But as he let it marinate, and then especially after seeing the finished film, Glover began to believe that Riley had written a classic. “This is a script that goes beyond,” he says. “Like Catch-22, you know, or Sweet Sweetback, Marvin van Peebles. They’re gonna be talking about this script.”

Sorry to Bother You premiered at Sundance to rave reviews and was bought by Annapurna, the production house behind The Master and Her, for seven figures. The company committed to a wide release and has put real promotional dollars behind the subversive comedy. Riley tells me he took a BoltBus from Oakland to LA for his first meeting with Stanfield—for an influential distributor to purchase his film wasn't just validating, it was life-altering. “That punk approach of 'We don't wanna get big' is really a bourgeois thing,” Riley says. “It's not a tactic of people that actually have been successful at changing things.”

But I ask Riley if he was at all wary to take money from Annapurna founder Megan Ellison, whose father, Oracle founder Larry Ellison, is the fifth richest person in the US and a major Republican donor. Left-leaning capital has always provided an economic motor for radical movements, he tells me. He respects the hell out of Megan Ellison for using her money to support leftist art, he tells me. But before he says either of those things, he adjusts his afro and tells me with a grin, “Even Marx sold books.”