Boots Riley’s radical vision

The artist and organizer’s debut film, Sorry To Bother You, tells a freakish story of labor and inequality set in Oakland.

Photographer Sasha Kelley
July 11, 2018

There were just enough clouds to temper the afternoon sun in West Oakland last month when Boots Riley rolled up in a grey ‘85 Mercedez-Benz to Alena Museum, a multi-use art and community space surrounded by other warehouses and Victorian houses. A visible figure in both art and activist circles in the Bay Area, Boots made his way through Alena’s airy and abundant space with familiarity, greeting folks along the way and stopping for a second to chop it up with the space’s director, Seven Asefaha. The scene at Alena is not unlike the ones from Boots’s debut feature film, Sorry To Bother You: a creative space with murals on one corner, a stage in another and in between, a table with a communal meal being shared by friends and collaborators. And like the characters Boots’s film, Alena and its community is dealing with capitalist forces beyond their control — an imminent eviction looms over Seven and the rest of the Alena team.


Nearly three decades ago, some miles west of Alena, Boots attended film school at San Francisco State University, the same school where his father, Walter Riley, studied and helped organize the 1968 strike that created the first ethnic studies program in the nation. In 1991, while still a student, Boots formed hip-hop band The Coup with Eric “E Roc” Davis, later incorporating turntable queen Pam The Funkstress who passed away late last year. Boots dropped out of school when the group landed a record deal soon after forming. The Coup went on to release six albums, two EPs, and tour the world with signature lyrics that relate life’s daily ups-and-downs to the systemic forces at work. All the while, Boots lived the manifestos from his songs, actively organizing and advocating for working class issues like wealth distribution and stronger unions in his Oakland homebase and beyond.

“I started out in radical movements before I thought that I was an artist,” he told me as we continued our chat in the empty ballroom at the Starline Social Club where The Coup performed their last show in Oakland in 2017. Boots has been active in that world since he was recruited by a youth organizer to help cannery workers on strike in Watsonville, a farming town in the central coast of the state, when he was 14. “I think that if you have a passion to have your art be for something more, then what goes along with that is establishing a base, having a community that you answer to, having a community that you represent, having a community that you engage with in a way [other] than through your art.”

“If you have a passion to have your art be for something more, then what goes along with that is establishing a base, having a community that you answer to.”


This week, Boots is crossing new artistic territory with Sorry To Bother You, which he wrote and directed. A dark, absurdist tale of capitalism set in Oakland, the film is rich in provocations about labor, love, and consciousness. “I finished writing it for the first time in 2012. By finished, I mean got to the end, the first time. But it was constantly in flux,” he explained. Since its inception, the story has lived a few lives including as book packaged with San Francisco publisher McSweeney’s quarterly print issue in 2014. But it seems that 2018 was the year it was fated to land in theaters with the social horror of Jordan Peele’s Get Out in our recent memory and the surrealist fables of Atlanta embodying the amorphous pressures that burden black ambition in America.

When Boots wrote the bends and twists of Sorry To Bother You, he couldn’t anticipate the current storytelling climate. Instead, he was devoted to feeling over structure. “When I was writing this, I'm thinking about people's feelings — how long they can be in this part, what the whole rhythm of the movie is. I don't think I'm new with that. [Maybe] coming from doing music, I was more keen to constructing something with that feeling.” He compares his method of structuring the film to writing The Coup’s song “5 Million Ways To Kill A CEO,” a song for the dance floor in a 9/17 count made more palatable by using a four on a floor beat. “I'm used to playing with the ideas of what art is supposed to be so I felt confident that's what I can do with this [film],” he said.

At the center of the warped Sorry To Bother You universe is Cassius Green, played by Lakeith Stanfield. The young man, who is on the verge of eviction, is so intimate with brokeness that he has no qualms asking for 40 cents worth of gas on the pump next to his disintegrating Tercel. But 40 cents is all Cassius needs to cruise through West Oakland to downtown for a job interview that injects him into the wicked world of telemarketing, a world that Boots is familiar with from his own experience working in a call center. Orbiting Cassius is Tessa Thompson’s Detroit, a painter and performance artist, who nebulously floats in and out of scenes in the film. There’s also Squeeze, Cassius’s co-worker and a labor organizer played by Steven Yeun. Detroit and Squeeze are attached to their values of anti-capitalism, though carrying out their principles in different ways, while Cassius follows the promise of money deeper into a heinous world.


“Every character in this movie I wrote as myself. There's an argument happening there between [Detroit] and Squeeze and Cassius. And that's an argument that's happening inside me all the time,” Boots told me. And so the film goes, arguing big questions but never making it a point to be didactic in answering them. To cut the weight of these larger-than-life ideas, Boots employed magical surrealism. “The reason I wanted to bend reality when talking about those big ideas is I wanted people to think about the points where reality bends in the world of Sorry To Bother You and what those points are in our real lives.”


Oakland, it turns out, is the perfect setting for those sort of big questions. The film paints quite a personal portrait of the town and the different nooks and corners that hold memories and private moments for those of us who’ve spent our days and years here. But it’s Oakland’s proximity, and now annexation, into the profitable but insular world of tech that mirrors Boots’s story. A crucial consequence of that annexation is the inescapable income disparity that places new developments yards away from homeless encampments. “When I finished writing it in 2012, there was all this stuff about homeless encampments that you could see. And at the time, there were homeless people but there weren't out in the open as much as was in the script,” Boots said. “That was always thought of as ‘That's going to be a production cost’ but by the time we started shooting, that was actually there and, you know, for me it was important. Not only for me but for the story, it was important to have that in there.”

The root of this disparity in Boots’s mind and in his film comes down to labor. “[A] lot of our time is spent talking about problems that have to do with the economic system that we live in. And the actual conflict point, the fulcrum that moves the motor of this economic system of capitalism is the exploitation of labor,” he explained. Boots is extremely well-versed in the history of labor in America and walked me through major work stoppages that led to policy change in America. But labor and class, he concluded, are subjects that “even the Left leaves alone.”

So how then did those subjects end up in one of the most anticipated movies of the summer, I ask him. “If I'm going to make a movie that's grounded in reality, and I have to go to the real operations and underlying currents of what that reality is,” he responded. “And that has to do with how we spend our day, and who we spend it for. That deals with labor.”

It should be no surprise to folks who’ve listened to The Coup that the frontman would find a way for those underlying currents to drive the stories he tells from the director’s chair. And now that he’s found a way to that chair, Boots has more stories to tell. “I have 20 years of ideas of movies I've wanted to make,” he said. It’s an exciting prospect for cinemagoers seeking strange dimensions whose knotted absurdities implicate parallel ones in our daily lives. “I think that so much of narrative structure that we see [in film] ends up informing our idea of how the world should be. So when our world is more complicated, we go into despair because we think, Why isn't it simpler? — even though life is never like that.”