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

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.”

Over the course of completing the film, Gallagher also formed the documentary film studio Rap Portraits with Atlanta-based music journalist Travis “Yoh” Phillips, a respected voice in hip-hop who has written for DJ Booth and Rolling Stone, among others. Phillips worked as a writer alongside Gallagher on May The Lord Watch.

In its first season of episodes — short vignettes that chronicle the “moments that make up a life pursuing the rap dream” — Rap Portraits gave viewers and fans intimate access to significant events in the lives of up-and-coming artists: EarthGang on the day their posse album with Spillage Village, Spilligion, came out; JID on the day he bought his first home. Already meaningful on their own, the bite-sized “Portraits” would end up serving a second purpose as a kind of incubator for the LB film that was yet to come.

“I had never done a documentary before,” Gallagher says. “I was barely a filmmaker. I learned how to make documentaries in the three or four years between us starting May The Lord Watch and putting out these short docs. All the stuff I learned on those [short docs] referenced and in turn informed how we were making May The Lord Watch.”

Rap Portraits’ first season culminates with a feature on Ibrahim “Ib” Hamad, the cofounder and president of J. Cole’s Dreamville Records, as the ferris wheels, fireworks and LED screens of the label’s annual, Raleigh-based Dreamville Festival dance in the background. Before the release of the hour-and-a-half-plus May The Lord Watch, the 14-minute episode on Hamad had been Rap Portraits’ longest entry to date. Gallagher says he hopes that with the feature-length documentary now under their belts, the filmmaking duo has proven themselves as more-than-capable longform storytellers.

“That’s the kind of space that we want to get into in the future, doing longer form stories more than short form. So May The Lord Watch is like a turnkey for us.”

The line between subject and producer has blurred in recent years. Popular documentaries like Michael Jordan’s “The Last Dance” introduced the idea that the main protagonist of a story could also have significant oversight of its telling. Phonte and Pooh both serve as executive producers on May The Lord Watch, but as viewers will note, the two emcees didn’t pull many punches when it came to revealing sensitive or damning material.

“If me and Pooh aren’t uncomfortable during parts of this, then we made a shitty documentary,” Phonte says. “You got to have some blood on the page. If you’re not the villain in at least part of this, then you’re not telling the real story because that’s just not how life is.”

Plotlines that played out publicly over their decades-long relationship — like when the group went viral on the Okayplayer message boards before social media made such things so commonplace, or the fallout with producer and former bandmate 9th Wonder and subsequent breakup — are presented in a new light. Yet, the film offers details about the group’s history that even their close friends might not have known.

“It’s a really comprehensive movie, tying the story not just of their career, but focusing more on their friendship and who they are as people beyond the music,” Gallagher says. “I think even the biggest fans will be surprised by how much information is new to them.”

Clips of influential figures spanning generations of hip-hop — from Questlove, to Drake, to Doja Cat — are woven into the film, speaking to the impact Little Brother had on the industry at their peak. But the history of their music career serves more as a backing track to the centerpiece that is the 20-year friendship between Phonte and Pooh. The documentary shows the two men struggle through the perils of success, reconcile past traumas in their personal lives, and rekindle a friendship that at one point had grown so distant as to be non-existent.

“When you get into your 40s, you develop a curiosity about yourself that just doesn’t happen at any other point in your life,” Phonte says. “In your 20s and 30s, you’re chaotic and it’s just about you. ‘This is who I am!’ Once you get into your 40s, it becomes, ‘Okay, I get this is who I am, but why am I this way? What made me this way?’”

Phonte said he watched a documentary on Netflix about actor, model and Baywatch star Pamela Anderson Lee. He explains that while his doc didn’t end in divorce like Anderson Lee’s, her journey of self-reflection after decades of hardship resonated with him nonetheless.

“When you really look back over 20 years of your life and how you spent your time, everything you went through, and the things that we had to learn on the fly,” Phonte says. “I mean, it makes you question everything.”

One of those questions, which we see both Phonte and Pooh work through during the film, is how to reconnect two lives, once upon a time joined at the hip, that had grown so far apart. Both men recount a momentous phone call — spurred by the death of hip-hop legend Phife Dawg in 2016 — made by Phonte to Pooh, after years out of touch. It’s an event also referenced by Phonte on the group’s 2019 song, “Everything”: 

“My man was heavy on my mind so I gave him a call, 
Remember when I couldn’t picture this vision at all, 
A little riddle only time intended to solve.”

“I had a relationship with Phife. We just had a conversation and the next thing I hear is he’s not here anymore,” Pooh says during the documentary. “It made me think about my own situation and then I started thinking about what I was holding onto as far as me and Tay.”

The two longtime collaborators, moved by the loss of their mutual friend, decided to reconcile their past disagreements that same day during a phone conversation that lasted hours. 

“Getting old and maturing are two different things.” says culture critic Tressie McMillan Cottom near the conclusion of the film (Cottom’s inclusion is welcome on multiple counts: in addition to being a New York Times columnist and MacArthur Genius, she also happens to be Phonte’s cousin). “You get old just by not dying. Maturing is a choice. I have been deeply proud of him, as someone who loves him, to watch him choose.”

Following their fated phone call, Phonte and Pooh spent the next couple of years reacquainting themselves, leading to the reunion show (including a brief trio appearance with 9th Wonder) at Art of Cool in 2018. They released the celebrated May The Lord Watch album and performed at Hopscotch Music Festival in Raleigh a year later. And in 2023, two decades after the release of their debut album The Listening, the pair hosted “Made in Durham: A Little Brother Block Party” in downtown Durham.

“How many people can say for the last 20 years that they’ve been getting up and working with their homies?” Phonte says. “That was something I think we took for granted because we were around each other so much. You’re just tired of those little moments that get under your skin but it takes a while to step back and say, ‘I’m tired of this, but dude, I could be sitting in a cubicle somewhere across from a stranger. I get to travel the world with my boys.’ What do we really have to be mad about?”

Shirlette Ammons, a rapper and film producer based in Durham, is a contemporary of Little Brother who also grew up in a small town in North Carolina, similar to Phonte, before launching her career in the Bull City. She serves as a producer on the documentary. Ammons says the group was instrumental in bridging distinct eras of hip-hop, and proving back in 2003 that artists from Durham could compete with the highest-caliber stars.

“They put us on the map but also just made us believers in our ability to be on par with anybody from anywhere,” says Ammons. “It’s an honor to chronicle this moment that shaped me and be able to see my homies get the props they deserve.”

The Southern Documentary Fund awarded the production team a $10,000 grant in 2021, but the film has largely been independently financed through friends, family and individual donors. This is by design. Little Brother found limited success, as well as significant headaches, working with major labels during their rise in the early 2000’s. It was Phonte’s experience self-publishing his Grammy-nominated R&B group Foreign Exchange back in the mid-2000s that solidified his stance on major labels: independence was not just a viable option, but the most rewarding path forward.

Streaming has changed the calculus for artists trying to publish their own music. Platforms like Spotify made it even easier to get songs into the ecosystem but greatly reduced the financial windfall, even for successful acts like Little Brother. Unless you’re in the highest percentile, making a living as an independent artist is far from guaranteed. Ammons says that, through the production of their music and the documentary, Little Brother has created a blueprint for other independent artists to emulate.

“It proves that this is attainable to anybody who’s willing to put in the work. The percentage of artists like Drake are few but the percentage of artists who put in the work to be what Little Brother is, who had a different grind and still have a following that perpetuated a career they've been able to make a living off of? That’s pivotal to see, especially told through their own voice,” Ammons says.

The May The Lord Watch documentary, which is available on Little Brother’s YouTube channel and now sits at nearly 250,000 views, is a benchmark for the early-Internet hip-hop pioneers, not a swan song. With a reunion album, international tour, hometown block party, and feature-length film under their belt since reuniting five years ago, Phonte and Pooh have their minds set on delivering their next great project for fans, whatever medium it takes.

“I thought that the Minstrel Show and all of that, I thought that was the ending,” Phonte said. “I didn’t realize that it was just the beginning.”

Justin Laidlaw, a reporter for The INDY in Durham, NC, is listed as an Associate Producer in the credits of May The Lord Watch.

Yoh Phillips has written for Super Empty.

Rap Portraits is frequently a creative partner and collaborator with Super Empty.

Phonte Coleman and Holland Gallagher are Partner-level supporters of Super Empty.

We do not expect most articles to require this many disclaimers.