The Black Watch’ Breaks Down Boots Riley’s ‘I Love Boosters’

A crew of couture criminals, luxury larceny, and plenty of Boots Riley-style absurdist adventure had BOSSIP and Cassius talking this week.

Today (June 12), the brands released a new episode of The Black Watch, an editorial-led series examining the biggest cultural moments in film and entertainment.

The latest installment of the series brings together BOSSIP’s Managing Editor Dani Canada, executive producer Serita Wesley, and comedian-writer Richard Jones for a candid conversation about Boots Riley’s brilliantly bonkers I Love Boosters.

The 2026 comedy-crime caper follows a group of fashionable shoplifters who steal designer goods from luxury retailers and resell them at discounted prices. The film stars Keke Palmer, Naomi Ackie, LaKeith Stanfield, Don Cheadle, and Demi Moore, and continues Riley’s tradition of blending surreal storytelling with sharp social commentary.

The discussion kicks off with the panel weighing the film’s overall entertainment value and whether Riley’s signature style still packs a punch.

Known for projects like Sorry to Bother You and I’m A Virgo, Riley has built a reputation for creating stories that feel equal parts absurd, thought-provoking, and unpredictable. According to the panel, I Love Boosters fits squarely within that tradition.

The group also spends time dissecting the film’s striking visual identity, which leans heavily into luxury fashion, consumer culture, and status symbols. But beneath the stylish exterior, the panel notes, Riley is making a much larger statement.

“Can we talk more about the social commentary that we’re getting from this film?” Dani asks. “Because it really is kind of talking about the ridiculousness of capitalism. It’s talking about how the boosters are taking from the rich to give to the poor.”

She also points to Riley’s commentary on luxury fashion’s relationship with communities of color.

“Boots also noted that it’s about big fashion houses and how they kind of steal from communities of color,” Dani says. “And then, we never get credit for it, so I thought that was really smart for him to put in there.”

Serita agrees, noting that the film’s themes feel particularly relevant in today’s climate.

“Yeah, I think it’s very timely for everything that’s going on in the country,” she says. “We see it time and time again. Every designer either wants to capitalize on us or they want to rip us off and not give us any credit.”

The conversation then takes a turn as Serita reveals something tied to the film.

“Wait, do y’all know any real boosters? Because I do,” Serita says. “I’m from Philly. I have some boosters in my family.”

“That’s real snitch activity right there,” Richard quips.

“I didn’t say who it was!” Serita fires back with a laugh.

Beyond the film’s social commentary, the group also praises Riley’s ability to assemble memorable ensembles. The cast of I Love Boosters sparks a larger conversation about the filmmaker’s creative partnerships, particularly his collaborations with Keke Palmer and LaKeith Stanfield.

“So we like Keke with Boots. We love LaKeith with Boots,” Dani says. “Who else do we want to see Boots work with next?”

“Lupita Nyong’o,” suggests Serita. “I want to see him with Lupita.”

Dani agrees, and Serita’s suggestion prompts a detour into recent online reactions to Nyong’o’s casting as Helen of Troy in Christopher Nolan’s upcoming film The Odyssey.

“I’m glad you brought up Lupita because I don’t know if y’all saw this whole controversy about her playing Helen of Troy,” Dani says. “People like Elon Musk are mad. They’re like she’s not the most beautiful woman in the world.”

“Yes, she is!” Serita insists.

Richard is equally unimpressed with the criticism.

“Yeah, Elon was like, ‘Well, he’s doing this to get awards.’ Duh!”

“I mean, why else would you make a film, right?” Dani responds.

“Exactly,” Richard says. “Because he’s not creative.”

He continues ripping into the SpaceX Founder.

He is a big idiot who fails upward. Elon Musk is not a robot. He’s just really good at—how do I put this? Oh, yeah, d*** riding.

The exchange eventually spirals into playful jokes about Hollywood, awards season, and internet discourse before returning to the film itself.

As the episode winds down, the panel agrees that I Love Boosters succeeds because it delivers larger conversations about wealth, culture, and who gets credit for shaping trends, just in the wonkily whimsical Boots Riley way.

Check out the latest episode of The Black Watch below.