Boots Riley, Marx Brother
Key takeaways
- In part, this was because Riley, who is fifty-five, wore a gargantuan, lumpy tomato-red felt hat with a wide brim, like the cowboy hat worn by Quick Draw McGraw in the old Hanna-Barbera cartoons.
- Oakland has become a city of artists, and often people just wanted to talk shop.
- A skinny man wearing a GoPro spotted Riley from a block away, whipped his head around like Wile E.
Riley, a critics’ darling, has big dreams for “I Love Boosters,” which he sees as his best chance to infiltrate the mainstream.Photograph by Bobby Doherty for The New Yorker Save this story Save this story Save this story Save this story On a cool, drizzly day in Oakland, California, the film director Boots Riley often seemed less like a person than like a landmark—clockable from a distance. In part, this was because Riley, who is fifty-five, wore a gargantuan, lumpy tomato-red felt hat with a wide brim, like the cowboy hat worn by Quick Draw McGraw in the old Hanna-Barbera cartoons. It was January, 2025, and Riley was taking a lunch break from editing his second movie, the caper film “I Love Boosters.” On his way to a burrito joint, he was stopped on nearly every block, often by fans of “Sorry to Bother You,” his surreal sci-fi movie about an Oakland telemarketer, from 2018, or of his equally loopy 2023 Amazon TV series, “I’m a Virgo,” about a sheltered thirteen-foot-tall Black teen-age boy. Some people quoted lines from his nineties hip-hop group, the Coup; others knew him from the 2011 protest encampment Occupy Oakland.
No matter who walked up, Riley slowed down. Oakland has become a city of artists, and often people just wanted to talk shop. A skate-store owner had plans for his own caper movie; so did a guy from a sign store. A musician called Big Hungry, who was starting a “digital music salon,” thanked Riley for hooking him up with a writing group. In each encounter, Riley, a chill, hangdog figure with mutton chops and a spray of freckles, was soft-spoken and receptive, curious and unhurried, but also a little elusive when necessary, knowing when to drift away. His friend Pete Lee, a photographer and a filmmaker, once recalled the default question that Riley uses to identify friendly semi-strangers he can’t remember: “So—what are you working on?”
On our way back to Riley’s editing suite, we passed a mural of Oakland notables, an image that included the hip-hop luminary Tupac Shakur and Pam the Funkstress—the d.j. for the Coup, who died at the age of fifty-one, after complications from surgery. A skinny man wearing a GoPro spotted Riley from a block away, whipped his head around like Wile E. Coyote, and barrelled toward us. “You should be on a mural!” the man yelled.