here are many points of entry to understanding Boots Riley, the 55-year-old filmmaker, artist, organizer, and self-proclaimed communist. The New York Times once called him a “veteran hustler,” an apt title considering that he’s been working since the age of 10. (His first job was selling newspaper subscriptions.) Ask Gen X or millennial men how they know Riley, and they’ll probably mention his work as a front man for the Coup, a politically conscious hip-hop group with whom he released six critically acclaimed albums between the early 1990s and 2010s. The chronically online might know Riley from engaging critics, haters, and fans on social media. And the rest of us recognize his name from the movies.

In 2018, Riley released his propulsive directorial debut 

The surrealist project, which was set and shot in Riley’s hometown of Oakland, took years to develop and introduced his artistic and political sensibilities to a new audience. Starring LaKeith Stanfield and Tessa Thompson, the satire follows the down-on-his-luck Cassius (Stanfield), who finds himself climbing the corporate ladder at a sinister telemarketing company thanks to a “white voice” he uses to speak to customers. It’s soon revealed that his success is undermining a broader unionizing effort.

When I spoke to Riley in April, he told me he considers 

to be the most effective piece of art he has ever created. Not only were responses to the film overwhelmingly positive, but some viewers went out of their way to tell the director their MAGA-aligned parents loved its anti-exploitation themes. Riley said, “They hadn’t been taught yet that they shouldn’t like it” — the “it” being capitalism. He also heard from people who played the film for their co-workers during union drives that proved successful. All this reconfirmed for the director that most people are to the left of not just Republicans but also Democrats, even if they don’t know it yet. It also reaffirmed a realization that Riley said came after many years of organizing: People rely on music and movies to inform their ideas of the world, and to accomplish his political goals, he needed to tap in. 

 was both a critical and a commercial success, and in 2024, Neon, the company that distributed 

with a $20 million budget, the company’s most expensive film to date.

landed in theaters in late May and represents an advancement in Riley’s artistry. After 

, the director went on to helm the critically acclaimed television miniseries 

, which follows a 13-foot-tall 19-year-old who becomes radicalized by a group of teenage political activists. With 

, Riley builds on his thematic interests in political organizing and anti-capitalist storytelling while embracing an even more surrealist and over-the-top style. The film, starring Keke Palmer, Naomi Ackie, Taylour Paige, Poppy Liu, Eiza González, and Demi Moore, centers on a group who shoplift stolen luxury clothing and sell it at a discount to their community. Led by Corvette (Palmer), the boosters uncover nefarious corporate plots and labor violations that force them to consider what it 

 takes to seize the means of production. The film is energetic and, at times, ridiculous, and it’s in that latter register that Riley engages in a clever subterfuge: By staging a heightened version of our reality, he exposes its inner workings and increases the potency of his political messaging.

hen I met Riley at the Criterion office, where he was filming his 

, on a beautiful afternoon in early April, he greeted me as if we were old friends who hadn’t seen each other for years. “I don’t remember you being so tall!” he said. Days before our interview, I had spotted the director in the audience at the first week of previews of 

, the Broadway revival of David Auburn’s play

With his signature Uptown Yardie crown (this one in blue) and a bright fuzzy orange jacket, Riley stood out in a sea of mutedly dressed theatergoers. After I introduced myself, a fan sheepishly asked him for a selfie (which he kindly obliged); another audience member whispered, “I love that guy.”

On our way out of the Criterion building, Riley conversed with our fellow elevator passengers, one of whom complimented his hat. Riley thanked the man and joked, “It’s where I keep my three other hats!” Later that afternoon, during our lunch at the Soho Grand Hotel, Riley treated every employee like a longtime pal, dapping up the hotel staff despite being in town only briefly to promote his film. As we talked, I wondered how much of Riley’s amiable disposition had to do with the kinds of jobs he’s had over the years. He’s organized with farmworkers, played in a band, and worked at a call center — a customer service job I consider unlike any other.

Throughout my late teens and early twenties, my most stable work experience was in call centers. My recurring stress dreams as a college student took place not in classrooms but in the fluorescent gray maze of cubicles where I’d sit for eight hours an evening, solving internet tech support issues for angry customers all over Canada. In one nightmare, I got fired because I kept forgetting the word for “modem.” Riley and I shared a laugh when I told him about my time in the customer service mines alongside a cast of colorful characters bound by a mutual need to make money. Working at call centers is one of the more dispiriting service jobs, because you spend hours being yelled at and feeling completely powerless. I asked Riley when he knew the life he currently has was possible, and his honesty was refreshing when he told me he saw his work as supplementary to his real goals. “I want to build this movement,” Riley said. “The job is whatever a job is, and hopefully you get a job where you can organize. That’s always the idea.”

iley was born in Chicago in 1971 to Anitra Patterson and Walter Riley, who were both organizers. Shortly after his birth, his family relocated to Detroit, where his father served as a local leader of the Progressive Labor Party and his mother led the organization’s youth work. When Riley was six years old, his father split from the party over disagreements about their approach to organizing and moved the family to the Bay Area, where Riley’s parents had met. In the introduction to Jesse Strauss’s book 

Civil Rights and Structural Attacks: Conversations with Walter Riley

, Riley reflects on how his household was a hub for organizers: “I was always just hanging on people’s legs while they talked, warming up to a post-meeting card party with music playing and people drinking beer and smoking cigarettes,” he writes. Growing up in this environment taught Riley how to bring people together, but he was never pushed into political organizing. His parents encouraged him to find his own path.

When he was a preteen Riley decided he wanted a moped. He got a job selling magazine subscriptions, and then graduated to delivering newspapers with older kids in his neighborhood, which required him to get up at four in the morning to knock on doors. In his teenage years, he continued doing almost any work he found, from washing dishes to handing out fliers advertising local pizza spots.

In the spring of 1986, when Riley was a teenager, a youth organizer from the Progressive Labor Party invited him to a weekend excursion with other people his age. He didn’t take the organizer’s entreaty seriously but halfheartedly agreed to meet the following Saturday. “I didn’t plan on being there,” Riley told me. The next weekend, he found himself in a van full of cute girls, heading to a beach in Santa Cruz. But there was a catch: Before the crew could lounge by the seaside, they had to stop by the Watsonville Canning and Frozen Food Company to support striking workers. The labor action began in September 1985 after management tried to decrease unionized employees’ wages by roughly 30 percent.

While in the van, Riley noticed the girls “talking about stuff that was on the news,” he said. “I was like, 

Wait, you’re really listening to that stuff?

” At that point in his life, the filmmaker was more focused on comic books than geopolitics. But it became clear during the ride that his peers were paying attention because they felt they could do something about the state of the world. “I started the ride off being attracted to these girls, and I ended it wanting to be them,” Riley said. He joined the Progressive Labor Party that year, about a decade after his father had left the group, and spent his first summer with the party embedding with farmworkers in the Central Valley and learning how to speak Spanish. At only 15, Riley committed to building a life as an organizer.

When I tell Riley that it’s hard for me to imagine a young person showing that level of discipline, he gently counters my cynicism. Activism among young people is far more widespread than most of us realize, he says. Around 1995, while on a break from performing with the Coup, Riley formed the radical collective the Young Comrades, which organized working-class teens in the Bay Area. He was inspired by learning about the Soweto uprising of 1976, where thousands of schoolchildren in South Africa protested their apartheid government’s mandatory lessons in Afrikaans, the language associated with the country’s white minority. Riley remembers watching a segment in which 12- and 13-year-olds spoke so clearly about international policy, capitalism, and various elected leaders’ stances on their cause. “The reason that they knew about this stuff was similar to the reason why those girls in the van did,” Riley said. “They felt they could do something about it.”

Riley left the Progressive Labor Party in the early ’90s. At the time, he thought the party was stagnant, inefficient, and overly involved in the day-to-day lives of members. Today Riley sees that approach as crucial to organizing. “You gotta be part of the community. You gotta be friends. You gotta be making sacrifices and be somebody that people want to make sacrifices for,” he explained. One statement from a party leader stuck with the filmmaker: “He would be like, ‘How you gonna get a bloke to go on strike if you can’t have a pint with them?’” Riley admits that the statement is sexist to some degree, but since that conversation, he has spent decades connecting with people on the ground, from his organizing efforts in the Bay Area to his work in Hollywood.

 was the next thing that I read the week after I lost a job for talking about Gaza and Palestine in the spring of 2024,” said Poppy Liu, one of the handful of actors in Hollywood who have openly supported Palestine amid industry blacklisting. Getting the script gave her hope, because it showed that someone like Riley — whom she affectionately calls the most “radical leftist, outspoken, communist, pro-Palestine baddie” — could still get work made. Before submitting her audition tape to play an organizer at a luxury brand’s factory in China, Liu spoke with Riley for about an hour over Zoom, discussing everything from their shared love of science fiction to the Communist Revolution happening in China the year after the Nakba.

 was unlike any other job she’s had, calling it one of her favorites. “We were all there because we were super excited about working with Boots and because we believed in him and we believed in the story,” she said. Liu likened the process to both a puzzle, in terms of understanding how to fit into Riley’s detailed screenplay, and a trust fall. “It’s cool to feel like you’re part of someone’s grand imagination scheme,” she said. 

takes place in a heightened version of Oakland, where a teleporter gadget can enact dialectical materialism, the Marxist theory that the world is always changing in a process driven by the collision of contradictions, and a high-speed car chase with skinless people takes over a mall. This dreamlike goofiness is an effective way of exposing how unreal our own world can feel sometimes and how helpless we might feel in the face of trying to change it.

During lunch, I tell Riley how challenging it can be to make an impact, especially when it seems that everything is just discourse. “I definitely find myself fighting cynicism,” he replied, but he has found a way to build his resolve to make change. The filmmaker tells me that a daylong strike like the Jan. 23 action in Minnesota gives him hope even as only a symbolic gesture, because it shows how a movement can be formed around any type of organizing, previewing what’s possible. “It’s about building power,” he said.

Riley sees part of his job as bringing coalition-building ideas to the forefront, with his films serving as a kind of instruction manual for society. He sends a clear message about the change that can happen while also revealing the contradictions of everyday life. People “go through a strike and they all of a sudden learn what side the police are on, they learn what side management is on,” he said. “In 

 people get involved in a struggle that says early on that things are made of labor. That’s a big thing for people.” He pointed out, “It’s built into the storyline.” The director also forgoes moral judgment in his films, whose protagonists make what might be considered the “wrong” choices, because that’s not what building a movement is about. “We can get the thing that we want by working together,” he said. “That’s the most efficient way, and that’s kind of what I put forward.”

Despite gaining mainstream recognition, Riley thankfully hasn’t fallen into the trap of adopting a more broadly palatable personality. This became more apparent after Oct. 7, 2023, when the mere act of signing an open letter in support of Palestine meant potential blacklisting. In November 2023, 

 that after Riley told his followers on X not to attend a screening of IDF footage of Oct. 7, the producer Marc Platt allegedly “texted WME leadership about why Boots Riley was still a client.” A Platt representative told Variety he “merely flagged” the posts. Riley did not back down, of course, and remains a client of the talent agency.

One reason Riley remains a countercultural figure in Hollywood is that he’s not trying to fit into the industry or necessarily get ahead. “I’m making my own thing,” he said, before adding, “I’m also the expert at making the thing that I make.” Although Riley is enjoying success few have achieved, he makes it clear he would still find a way to make his work if he lost the support of a studio such as Neon. If his years of odd jobs and organizing have taught him anything, it’s how to make himself popular enough to be heard.

Hammer&Hope

Sarah Hagi

@KindaHagi

Contributions

Issue

11

Boots Riley Wants You to Organize

FREE
TO READ

SIGN UP
TODAY