Twenty Years Later, Little Brother Get Their Feature Film Closeup — Their Way

The strained relationships, false starts, chance encounters and life lessons that led to May The Lord Watch: The Little Brother Story.

Twenty Years Later, Little Brother Get Their Feature Film Closeup — Their Way
Images courtesy of Little Brother. Super Empty illustration © 2024

Editor's Note: A preview of this article is available without logging in, but a free membership/email subscription is required to read it in full. For the long explanation of why, you can read more here. For the short explanation: it's the only reliable way to ensure our original, long-form, NC hip-hop writing finds its way to you every week. Tap the green button in the bottom right, and subscribe for free in a few seconds. If you've already subscribed, thank you!

Over their storied, two-decade careers, Phonte Coleman and Thomas Jones III have performed for thousands of fans across the world as the rap group Little Brother. The two emcees are well-known for their chemistry and charisma on stage — their shows flowing effortlessly between piercing rhyme schemes, monologues about the tribulations of life, and what at times amounts to a stand-up comedy set from Coleman, who raps mononymously under the name Phonte (one live-show standard: “Our shows end at 11 pm. Our fans got jobs!”). Watching the duo in their natural setting, it’s hard to imagine two people more comfortable or at ease.

But on a surprisingly warm November evening last year, back in the city that birthed their music careers, Phonte and Jones III, aka Rapper Big Pooh, waited anxiously in Durham’s Carolina Theatre. This time, the hundreds of fans in attendance weren’t there to take in the familiar live-show routine that Phonte and Pooh could, at this point, probably do in their sleep. They were there to see something entirely unprecedented in Little Brother history: a feature-length film called May The Lord Watch, named after their 2019 album of the same title, that documents the ascension, breakup, and eventual reunion (sort of) of the acclaimed hip-hop group whose journey began in the dorms of North Carolina Central University.

The film’s director, Holland Gallagher — a filmmaker and screenwriter based in New York City — lived in Durham for years after graduating from UNC-Chapel Hill. But it wasn’t until a random encounter in the Uber line at the Los Angeles airport, in 2018, that he met Phonte — pitching the emcee on his new show HYPE, a web series based on observations about life in Durham and the pursuit of happiness. By the time the show debuted later that year with a screening at Carolina Theatre, Phonte had come on as an executive producer.

Phonte says the way Holland bootstrapped the film felt familiar to his own experience making music.

“It reminded me a lot of how we created The Listening,” Phonte says. “It was that same spirit of just making use of the tools that you have instead of making excuses. That really spoke to me.”

That same weekend, Little Brother sent shockwaves through the hip-hop world by reuniting as a trio for an appearance at Art Of Cool Festival after rapper Royce Da 5’9” couldn’t make his set. The group hadn’t performed together in nearly a decade, after personal drama and the pursuit of other projects fractured their relationship back in 2010. Following the performance at AOC Fest, as well as Little Brother’s subsequent decision to start working again — as a duo, sans 9th Wonder — Phonte invited Gallagher to his home to pitch him on telling the full Little Brother story.

Five years later, the rapper and filmmaker were back in the same venue on yet another Thursday night — same as the HYPE premiere — to present the documentary they produced together.

During the Q&A after the screening, an audience member asked why Gallagher, a newcomer to the world of full-length documentaries, was tapped to deliver the doc. Phonte said his distance from the early history of Little Brother afforded Gallagher objectivity and a focus on what would resonate with a broader audience, not just hardcore listeners.

“The thing that a lot of people didn't know was that Holland was up on us and had respect for us but he wasn’t a super LB fan like that,” Phonte told the audience. “I saw that as a positive because the last thing you want is somebody coming in to direct your documentary, and they think they already know the story. You don't want somebody to be like, ‘So tell me, when y’all recorded that B-side in Japan in 2002.’ It's like, dude, that's a fucking podcast. You don't want somebody who's gonna go so deep into the weeds that it's just inaccessible to anyone else.”