The director’s zany movies combine pop aesthetics with radical politics.
By Emily Nussbaum
Photograph by Bobby Doherty for The New Yorker
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.
“I’m not done yet!” Riley shouted back.
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