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The Radical Optimist

Boots Riley, cofounder of hip-hop's the Coup, is taking his satirical vision to the silver screen, backed by a cast of comedic all-stars.

Two decades after the Coup dropped its first album, cofounder Boots Riley is ready to start making movies.


Boots Riley, avowed communist and founder of the Oakland-based hip-hop group the Coup, is making a comedy—a dystopian, sci-fi comedy.

If you only know Riley, 45, from his political movements (Occupy Oakland) or his albums and singles (Pick a Bigger Weapon, “5 Million Ways to Kill a CEO”), that might come as a surprise. After all, he’s the guy who went on a news show in Cleveland to promote a music festival and instead denounced capitalism. He believes that the withholding of labor would have been an effective means of securing an indictment in Ferguson. If you want to sign a petition denouncing Israeli apartheid, you can affix your name right next to his.

So, surprise: The movie is going to be funny. But then again, so is Boots Riley.

Riley, says admirer Patton Oswalt, is “the closest thing hip-hop has to a Sarah Silverman or a Dave Chappelle.”

“People get the impression from afar that he’s this strident, dour dude because he’s got messages in his music, but Boots is a hilarious guy,” says Adam Mansbach, author of the bestselling children’s book for adults Go the Fuck to Sleep, who frequently invited Riley to be a guest on his former radio show, Father Figures. “It’s just that when you start talking about how you’re a commie rapper, people just don’t associate that with a lighthearted, humorous take on things.”

Riley’s brand of socially conscious hip-hop is filled with messages about sexism, racism, gentrification, genocide—even the need to fund scientific research. But all of this comes with a comedic spin (and danceable beats). After the Occupy movement petered out, Riley released “The Guillotine,” an anthem for the underclass ready to rise up against the powers that be: “No, you can’t outvote ’em / The rules are still golden / Only jewels we holdin’ / Is if we guardin’ our scrotum.” In “Me and Jesus the Pimp in a ’79 Granada Last Night,” a particularly dark song about a man killing his mother’s pimp, he raps, “Microsoft muthafuckas let bygones be bygones / But since I’m Macintosh, Imma doubleclick yo icon.”

“His music is really smart and wicked,” says Patton Oswalt, the comedian and longtime fan who pantomimes his way through the video for “Magic Clap,” a song off the Coup’s most recent album. “He finds a way to be lighthearted about dark stuff, which is what makes it land. People like him. He’s the closest thing hip-hop has to a Sarah Silverman or a Dave Chappelle.”

A few years ago, in search of inspiration for his next album, Riley funneled his wry sense of humor into a screenplay called Sorry to Bother You, the story of a thirty-something telemarketer named Cassius Green who finds a way to dub over his voice with a white actor’s. Massive sales ensue, Cassius moves up the ranks, and soon he finds himself selling slave labor and weapons of mass destruction for a company that’s creating a race of ultra-efficient half-horse people called Equisapiens.

If it sounds weird and macabre, it is. But it’s also so funny that cultural darlings from Oswalt to Dave Eggers to the Lonely Island guys are on board. “It was one of the best things I’d ever read in that medium,” says Eggers, novelist and editor of Timothy McSweeney’s Quarterly Concern. “He’d created a wholly credible and terrifying alternate Oakland that asked crucial questions about labor, democracy, technology, gene modifications—and also the stupidity of VIP sections in nightclubs."

Making a movie is not out of character for Riley. That’s one of the things he says people get wrong about him. He may have spent the last two decades of his career making music, but his roots are in theater, and he’s always been a storyteller. When Riley was young, his grandmother, Anita Patterson, directed the Oakland Ensemble Theater. During his junior year at Oakland High, the drama club wanted to stage a modern musical. Riley (then known as Raymond) had never rapped before, but he took a stab at writing and performing for East Side Story and “nobody booed, so I thought, maybe I can do this.” He acquired his nickname at around the same time, when he attended high school grad night in a pair of Florsheim boots that his father had bought him. The name stuck—and, for a budding performer, it was a great way to be remembered.

Even as a teen, Riley was an activist. His father, Walter, now an Oakland civil rights attorney, was a child of the Jim Crow South who was organizing sit-ins and working with the NAACP before he even graduated from high school in North Carolina, class of ’63. As a student, Walter helped to organize the 1968 strike that brought ethnic studies to S.F. State while participating in Students for a Democratic Society and the Progressive Labor Party. This is the world that Raymond “Boots” Riley was born into. He was still in school when he began identifying as a communist, joining the Progressive Labor Party and the International Committee Against Racism and, he says, clashing with his high school principal over history lessons that portrayed the Black Panthers as “the black KKK.” (According to Riley, the principal got on the campus loudspeaker and said, “Raymond Riley is a communist. Don’t listen to him.”)

After high school, Riley wanted to use art to get his message out, but “theater was nothing,” he says. “It was too small for what I wanted to do, for the impact I wanted to make.” Instead he went to film school at S.F. State and started writing the soundtracks for his projects. In 1991, Riley and fellow UPS worker Eric “E-roc” Davis founded the Coup, and the next year they were the first West Coast rap group to land a deal with golden-era hip-hop label Wild Pitch Records. That’s when Pam the Funkstress came in. The San Mateo–based DJ was one of the best Riley had ever seen, and with a deal in hand, he approached her while she was performing at a Tupac Shakur album release party. Riley dropped out of film school, and the trio put out Kill My Landlord in 1993. It’s not Riley’s favorite—in retrospect, he wrote that “much of the album comes off more like a political pamphlet”—but it landed the Coup on Yo! MTV Raps and BET’s Rap City, and it still reaps critical acclaim. (Not long ago, NPR ran a story called “20 Years Ago I Heard the Perfect Rap Song,” a tribute to the track “Not Yet Free.”) 

In ’94, the group’s “Fat Cats, Bigga Fish” became one of the most requested songs in the Bay Area; one L.A. radio station started playing it on the hour. Soon the Coup were selling 5,000 albums a week in Chicago and L.A. Two years later, Riley sang in E-40’s “Practice Lookin’ Hard” video alongside Shakur. But even with all the success and attention, Riley was frustrated. At 24, he felt like he wasn’t doing enough to change the world. “A lot of my heroes were revolutionaries who were making an impact at 19,” he says. “I thought, ‘Fuck, I’ve wasted my whole adult life being an artist.’ And I quit.”

He left the Coup to form the Young Comrades, an activist group that used music and rallies to fight against issues like Oakland’s “no cruising” ordinance. Later, during Occupy, he called his record label, Anti-, to say that his forthcoming album would have to wait. “Most musicians justify their career building and say, ‘Once I’m in a position to be heard, I’ll build a movement,’” Mansbach says. “Boots is the opposite.”

The Young Comrades didn’t last long. In 1998, the Coup were back with Steal This Album, but it was 2001’s Party Music that put them into mainstream America’s crosshairs. Not only did the original cover art depict Pam the Funkstress and Riley cavorting in front of an exploding World Trade Center (imagery designed well before 9/11 that was dropped prior to the album’s November release, but that lives forever online), but the album also featured the song “5 Million Ways to Kill a CEO.” Though the lyrics are more funny than incendiary—“You could throw a twenty in a vat o’ hot oil / When he jump in after it, watch him boil”—the song didn’t endear Riley to the conservative set. While the Washington Post praised Party Music’s “jarring ingenuity, soul and wit” and declared it the best album of the year, a Fox News pundit called Riley “a stomach-turning example of anti-Americanism disguised as highbrow intellectual expression.” It’s a quote Riley loves so much, he now includes it in his bio.

Riley’s signature mutton chops are recognizable in Oakland, so sometimes he heads to San Francisco to work. One day in 2013, as Riley was walking down Valencia Street, he ran into a friend who was chatting with author Dave Eggers. Riley had never met Eggers, but the two men got to talking about books and movies, and Riley casually mentioned his screenplay. When Eggers later read it, he loved it. “It’s really fall-down funny on the page,” he says. “Then there’s the terrifying undercurrent of a new kind of slavery overtaking an unsuspecting city. It’s a surreal and brilliant vision.” 

Sorry to Bother You is drawn from Riley’s time as a telemarketer in the 1990s. Organizing with the Young Comrades left him short on cash but great at sales. But he quickly learned to change his voice: “If you were black, they didn’t want to give you their credit card number,” he says.

That’s where Cassius Green’s magical white voice came from. The rest of the story—the slave laborers working in fancy dorms, the people living on the streets, the characters trying to stay true to their art, the horsemen—was inspired by our technological trajectory. “We’re being made to be so efficient that you feel guilty if you’re not sitting on the toilet writing an email,” he says. “We’re all being made to be monsters.”

In 2014, Eggers published Sorry to Bother You in issue 48 of McSweeney’s, and Riley landed in the San Francisco Film Society’s workspace alongside film producer Jonathan Duffy and his partners, George Rush and Kelly Williams. When Riley showed them his script, they signed on.

With producers on board, Riley headed to the Sundance Film Festival in 2015. One night in Park City, as Riley was standing in line for a drink, he ended up waiting next to Jorma Taccone. Taccone, who along with Andy Samberg and Akiva Schaffer makes up the comedy trio the Lonely Island—creators of Saturday Night Live favorites like “Dick in a Box” and “I’m on a Boat”—has been a huge fan of the Coup since he was in junior high. The group actually wrote a parody of the Coup’s “Pimps (Freestylin’ at the Fortune 500 Club)” called “Santana DVX” for its 2009 album. In it, guest E-40 raps as Carlos Santana about his eponymous (fake) champagne label. “I used it as an icebreaker, and we started talking about hip-hop and the Bay, and I told him what a huge fan I was,” Taccone says. “And then he happened to mention that he’d written a script.”

Now, five years after Riley first wrote Sorry to Bother You on a whim, the comedy is about to get made. Riley refined the script at Sundance Labs; it’s scheduled to start shooting later this year, and actors including Oswalt and Arrested Development favorite David Cross have committed to appearing in it. The Coup will write a new soundtrack (the original Sorry to Bother You album came out in 2012); Rush, Williams, and Duffy will produce along with Party Over Here (Taccone, Schaffer, and Samberg’s production company); and Oakland indie act Tune-Yards is handling the score. Riley hopes to premiere the film next year. 

Though the film will definitely be very dark—the Equisapiens are creepy even on the page, before being rendered in makeup and prosthetics—the intention is to make people think and laugh, in the same way that Riley’s songs are supposed to make people consider revolution but dance while they do it. It’s an approach honed from his days as an organizer. “So much of what’s considered political art is doom and gloom,” Riley says. “But anger is not what motivates people to do things. My art is not just about telling people about the problems of the world; it’s about showing them how they change it. It’s optimistic.”


Originally published in the May issue of San Francisco

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