During our walk through Oakland, we passed a tiny vintage clothing store called Regina’s Door, and its owner, Regina Evans, a congenial woman in a headwrap, emerged to hug Riley. In addition to selling clothes, the shop offers financial support and “creative arts healing” to survivors of sex trafficking and provides a venue for Evans’s plays, which Riley has attended. She gave Riley a happy update on one of the women she helps support, then let him know about a new play she would be mounting soon in Berkeley. “It’s very weird and different, about a slave who kills herself and rebuilds her life with two spirits she can’t really see but knows are there,” Evans said. “Writing it, I came to a standstill and got scared: ‘I don’t think this is gonna work.’ Then I started reading your movie reviews, and everyone’s saying, ‘It’s crazy but it’s awesome.’ I said, ‘Well, Boots wrote a crazy script,’ and I started writing again.”

“That’s beautiful,” Riley said, nodding.

Much of “Sorry to Bother You” seems outlandish — on its surface. The film has a charmingly handmade ambience of hyperreality: puppetry, stop-motion animation and dozens of little offbeat details, like Cassius’ broken windshield wipers, which he must operate by yanking a piece of string. Dave Eggers sees the movie as carrying forward a tradition of “dirty surrealism, where it’s not about perfect special effects, it’s about the rawness of the subconscious. Your dreams don’t have high production values! Your nightmares are rough. Spike Jonze and Charlie Kaufman and Michel Gondry have done such incredible work in that realm, but until Boots, it’s been a while since anyone else has.”

In Riley’s hands, these fantastical elements have a clear dramatic purpose. Cassius’ ability to speak with a “white voice” (provided by David Cross) is a way to poke fun at perceptions and performances of racial identity. The film’s central villain, a company with the innocuous name of Worry Free, signs laborers to unpaid lifetime contracts in exchange for a guarantee of meals and glammed-up prison-style housing — bunk beds crammed beneath chandeliers. Worry Free’s scheme seems a touch less far-fetched when considered alongside old company-owned mining towns, Foxconn City in Shenzhen or even tech campuses with their free amenities and napping pods, meant to blur the line between work and life and extract more value from employees in the name of providing perks. Eggers, a longtime San Franciscan, said: “When I read Boots’s script, I’d just published ‘The Circle’ ” — a 2013 dystopian novel set in Silicon Valley — “and it struck me that we were both picking up on changes we’ve seen in the Bay Area. There’s this strangely sinister cast to life here sometimes, where it’s still idyllic and free and open but also there’s a sense of consolidation of power, of wealth and of control that was never part of the Bay before.”

Cassius begins the movie broke and aimless, renting a room from his uncle Sergio (Terry Crews), who is facing imminent foreclosure. When the telemarketing firm rewards Cassius’ supernatural cold-calling prowess with promotions and praise, these represent a concrete means to save Sergio’s house and the first time in Cassius’s adult life that people in power have told him he’s good at something — even if that something turns out to be shilling for weapons manufacturers and Worry Free (whose sarong-sporting chief executive is played with slick, winking malevolence by Armie Hammer). Cassius comes to see his striking co-workers and his radical artist girlfriend, Detroit (a transfixing Tessa Thompson), as impediments to the blossoming of his own excellence, but Riley and Stanfield make it compellingly tough to dismiss his motivations here as merely selling out. “Boots and I wanted to make sure he was relatable,” Stanfield told me, “a normal guy in an otherworldly situation that actually has a lot in common with real-world situations.”

Among the questions the movie raises is whether black success within capitalism is something to reflexively celebrate or whether the success of individuals who belong to an exploited class serves to ratify and consolidate — rather than thwart or ameliorate — the system doing the exploiting. Discussing this question, Riley used the example of the resolutely capitalist Jay-Z: “When people listen to Jay-Z, they’re working all day or trying to work and pay their bills, and what they hear is someone who’s free. Who doesn’t have to worry about the electricity. But all we’re taught is that those who are rich deserve to be rich because they worked harder than the rest of us or they’re smarter. And this may be true of some of those folks, but there are definitely very poor people who are very smart and work hard. It’s just that this system can only have a few people on the top. So Jay-Z is saying: ‘You can do this, too, I’m trying to give you game,’ and it ends up explaining poverty as a system of bad choices. Yes, maybe you can make better choices and be the crab that gets out of the bucket — but that’ll be at the expense of all the other crabs in the bucket.”

In the past, Riley has criticized Hollywood as abidingly reactionary in the stories it tells about black people: “All these movies — whether it’s ‘Menace II Society’ or ‘Boyz N the Hood’ — the moral is ‘Move some place else and everything’s better,’ ” he has said. “And the message is always ‘We’re destroying ourselves,’ and there’s no mention of anything systematic.” At one point, drinking coffee on stools in an uptown cafe, I brought up “Black Panther.” Riley told me that he admires Ryan Coogler and considers him “a mentor,” but his praise for that film came with an asterisk: “It was great — for a superhero movie. One of the best I’ve seen. But I have a problem with superheroes in general, because, politically, superheroes are cops. Superheroes work with the government to uphold the law. And who do the laws work for?” Riley answered this question with a smirk. “Put it like this: We all love bank robbers, because we know that in the two sides of that equation, the robbers are the ones to root for, not the banks. Only in superhero movies and the news do they try to make us think we’re against the bank robbers!”