How Little Brother and Rap Portraits Made One of The Year’s Best Music Documentaries

For some, life is a series of chance meetings with historical consequences. Little Brother, the trio comprised of rapper/singer Phonte, rapper Big Pooh, and (formerly) producer 9th Wonder met on the campus of North Carolina Central University and went on to craft one of rap’s most beloved catalogs. Their story was chronicled in the recently released documentary, May The Lord Watch, currently available on YouTube. The film was crafted by Travis “Yoh” Phillips and Holland “vacayvacayvacay” Gallagher of documentary studio Rap Portraits — whom Phonte connected after meeting Gallagher at an airport and later introducing him to Phillips. Over three years, the two duos collaborated on a 100-minute documentary that narrated Phonte and Pooh’s rekindled friendship as much as it does Little Brother’s musical legacy.

“The first version of the movie was really the Little Brother story, and this version of the movie is the Pooh and Phonte story,” screenwriter, director, and documentarian Gallagher tells Rolling Stone. 9th Wonder didn’t participate in May The Lord Watch. In 2019, Gallagher crafted two short Little Brother documentaries: one about the group’s 2003 The Listening album, and the other about their reunion show at the 2018 Art Of Cool festival. The two documentaries were meant to lead into the feature-length film, but Gallagher says a prior iteration of the documentary was scrapped because there was too much flux with the recently reconnected trio. In 2007, producer 9th Wonder parted ways with Little Brother, and in 2010, Phonte and Pooh disbanded the group. Rap Portraits vied to chronicle the group reconnecting during that period, but Gallagher says it wasn’t time yet (and 9th ended up bowing out of the 2018 reunion).

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“It was the wrong tone, they didn’t have the time and the ability to reflect,” he says. “The space [allowed us] to look back and then be able to tell the whole story a little bit differently.” In 2021, Gallagher brought in his Rap Portraits colleague Yoh, an accomplished rap writer who was seeking to tell stories in a new format. The documentary’s production was altered by the COVID pandemic, which forced them to join the rest of the world on Zoom for weekly production meetings.

“When we were shooting, at times it was a lot of movement,” Yoh says. “A lot of moving pieces, putting together interview questions for everybody, [and] going through the interviews after they were recorded because the interviews themselves were almost two hours a piece.” The two say that the interviews with main subjects Phonte and Pooh were seven and “almost six” hours, respectively.

Rap Portraits began with a simple edict: “Everything about Rap Portraits was about picking a significant day in the artist’s life,” Gallagher says. “Mavi’s first sold-out show in New York was our first example of if you put a camera on an artist on the right day, you never know what you’re going to see. We try to repeat that with JID buying his first home, or Wynne’s first radio freestyle.” The two say they’re looking to subvert rap’s typical fluff documentaries with two guiding principles: Gallagher champions doing “vérité” work while Yoh says he’s curious about “which stories are untouched?”

Phonte told Rolling Stone in February that he vied to collaborate with Rap Portraits for their storytelling skills and because their generational gap offered a fresh perspective on Little Brother. Yoh concurs, and his retrospective introduction to their catalog allowed him to contextualize them uniquely. “I never thought of myself as this huge LB fan, until now,” he says. “Now I go back and listen to the albums like, ‘I can’t believe we had Kanye at the same time as LB.’ They’re doing the kind of raps that people love Kanye for, but it didn’t feel like they were getting the same kind of attention. Think about when Foreign Exchange happens, 808s and Heartbreaks is right there. Phonte is singing a year before Kanye. It’s all happening at the same time, and yet it felt like one was very mainstream and one was very underground.” But now Rap Portraits is shedding light on what happened for the whole world.

We spoke about crafting May The Lord Watch, working around 9th Wonder’s absence, and what’s next for Rap Portraits.

What was the catalyst for creating Rap Portraits?
Yoh: Holland hit me up to do a consultation for Hype season two, where he was thinking about expanding that world. That’s what got us back on the phone just talking about hip-hop. In those conversations we were talking about how we’re interested in documentation and more fly-on-the-wall type of storytelling, just getting into the rap world with a camera.

And as we’re having these conversations, we see that video of Mavi rapping on a train before his New York show, and we were like, “That’s it. This is the person, this is the kid. He has a sold-out show tomorrow.” Holland knew Mavi’s former manager, and he was like, “I’m going to hit him up.” I DM’d Mavi on Twitter, and I was like, “Hey, can we put a camera on you tomorrow?” And everyone said yes. So in 24 hours we put together the first Rap Portraits where Holland leaves North Carolina to go to New York, has never met Mavi before, touches down, and follows him with a camera the entire day. Holland comes to Atlanta afterward and we put together the first Rap Portraits together, just discussing how we want it to feel, what we want it to look like, and things of that nature.

The original idea was to maybe collect nine of these things and put them out as a collection. But we shot Mavi in January 2020. By May, we’re in full pandemic, and that’s when we decided to release the first one as a one-off and see what it would be like. And I don’t think we had a name for the series at first. Rap Portraits was a placeholder.

Yoh, how did you shift your storytelling talents from editorial to video documentary work here?
A big part is Holland allowing me to have a voice in it because he’s coming from the filmmaker background. When he brought the footage from the Mavi doc to Atlanta, and allowed me to have input about how the story moves or where certain things should go, I used all the ways that I would editorialize my writing, and I saw it in the same storytelling. When you do an interview, Andre, and you have quotes, you know where to put the quotes at, and you know where you want your intro at, you know how you want to close.

It’s very similar except you have footage. You go through two hours of footage and you’re trying to organize everything in the same kind of way that you organize a transcript, or you organize an op-ed. It’s really organizing your ideas in a way, and doing that so often for DJBooth, I think it gives you a sense of intuition where you want, how you want something to start, how you want people to feel in the middle. You know what a good closing is.

Gallagher: Documentary as a medium is sort of the hybrid between filmmaking and journalism. And so in the Little Brother doc, which is an interview-based doc, it’s only going to be as good as the quality of the interviews we have with which to work. A lot of that is credit to Yoh for writing these questions and getting thoughtful responses that we can then shape into a concise story.

Can you take me into the moment when Little Brother first asked you to come in with them to create a documentary?
Gallagher: That weekend after Phonte had come to the Hype premiere and they had done the Art of Cool show, which is the first show that they’d done in 15 years, Phonte invited me to his house. We talked for four hours about all sorts of stuff. The show that I made was about the rap scene in Durham, so we talked a lot about where it is now versus where they were then.

We really aligned. He found out that I had done most of the parts, I had edited it, I had done the score for it. It was really DIY. He said [it reminded] him of how they had made The Listening, where they’re in the dorm room and they just have a mic with the “sock condom” on it, and they’re all laughing at the skits. And you can hear it in the background of the record.

That DIY ethos and independence is what hindered us to begin with. But again, how we started is not how we finished. When me and Yoh started developing a voice as a team with Rap Portraits, it all came full circle. And Phonte was like, “Well, why don’t we just do it with y’all? Nothing would make more sense than that.”

You referenced that you had an initial iteration of the documentary but you started over. Can you take me into what the initial roadmap for that documentary was, and why y’all decided to rehash and try again?
Gallagher: There was a pretty big learning curve on the first version. And also there was a lot that was still [going on] with the group while we were making the first version. This was coming off of the Art of Cool reunion show, and it was that period that you see in the doc where maybe 9th isn’t going to be a part of the group again, and maybe this is going to happen, maybe that’s going to happen. And so as we were making it, A, that was developing, and B, as it concluded that chapter, it was a little raw, I think, for the guys.

It was the wrong tone, they didn’t have the time and the ability to reflect. The space [allowed us] to look back and then be able to tell the whole story a little bit differently. Also, I think the first version of the movie was really the Little Brother story, and this version of the movie is the Pooh and Phonte story. Little Brother’s story is a part of that, but it’s not the whole story. All that stuff from their childhood, as an example, wasn’t in the first version at all. We didn’t go to Red Springs or Virginia in the first version.

How did you navigate the absence of 9th Wonder in the documentary?
Gallagher: From a process perspective, it was just a lot of conversations. That year that we were doing the interviews, we were on Zoom every week with the guys talking about how things are going to fit in this section, and how things are going to fit in that section. And I think with 9th not being involved, obviously you don’t get his perspective on events that happened to him, which as an audience, you might be wondering. When Pooh and Phonte are talking about not inviting him on the tour, you would want to know how he felt about that.

But I think as the documentary unfolds, you come to realize that the heart of the story is these two men learning how to communicate with each other. And the whole reason that it doesn’t really work out with 9th in the end is a lack of communication. And so that being the center point of the story itself, I think exemplifies anything that we would want to say about that part of the relationship.

Yoh: Me and Holland are both coming in unbiased because we weren’t there with them, so we don’t have the relationship that they have with 9th. So for us, it’s about making sure that everything stayed fair. And the guys definitely had intended on making a fair doc as well, but again, they’re telling their side of the story. We made sure that 9th got his flowers as a producer, and we made sure people understood how significant 9th and Phonte meeting was, that they met over The Source magazine. There was a bond there from the start through hip-hop. But I think that the true building of the story is poor communication, and how if the guys could have communicated better or had the skillset to communicate better, who knows what happens to the LB story across the board.

Can you speak to how much the daily grind of creating the doc uprooted your everyday life?
Yoh: Well, for me, one, it was the inclusion of the Zoom calls. I went from not talking about this thing to talking about it every week. Before we were building out the story, we were just talking about the story. And then when it came time for the interviews, it was scheduling really. We went to Boston for Dart, and then we went to Connecticut for Big Dho, and we did that two days apart. So when we were shooting, at times it was a lot of movement, a lot of moving pieces, putting together interview questions for everybody, going through the interviews after they were recorded because the interviews themselves were almost two hours a piece.

One of the funniest things about the documentary was when we interviewed Phonte’s mom. His son was there, and her interview was like two hours. His son was like, “Well, I hope you know grandma, you only going to be in there for five minutes.” And I was like, “Damn, why’d you tell her that?” But he wasn’t wrong. It became a process of [having] conversations, building out questions, doing the interviews, watching the interviews, trying to extract the parts and pieces that help tell the story, and repeating that over and over and over again.

Gallagher: Yeah, it was a grind. It’s a lot of travel. Editing is a real beast to overcome. But when you’re running around and getting this stuff, you’re accumulating a map. It’s like sculpting, you need the stuff to sculpt with. The best material is going to give you the best thing in the end, so you have to run around and get the best thing that you can. And then from there, you’re just chipping away. You get the first cut done and you’re exalted, and then immediately you’re like, “Oh my god, there’s so much more work to do.” It just really feels like it’s never going to end.

Yoh: I remember when the doc was two hours, and it was like, “We’ve got to cut this down.” And I was like, “Cut what?” I thought about Drink Champs being three hours. And it’s like you can sit down in front of a microphone and talk for three and a half hours, and just upload the whole thing-

Gallagher: Once a week. You could do that every week. But [we spent] two years on something that’s an hour and a half.

Phonte has talked about the vulnerability needed to have the best documentary possible. Not just portraying what you want to portray, but showing yourself being vulnerable and honest. Did you experience that from day one that they were very much, “Whatever you want to ask?”
Gallagher: 1,000 percent. From the beginning through the end. So often when you have a music documentary with the artists involved, it comes off a PR piece or a “people didn’t appreciate us” kind of thing, which maybe was your expectation coming into this movie. But [there’s] the point in the movie when Phonte does not call Pooh in the hospital, which is the low point, emotionally, of their relationship. For a while, after Phonte explains why he didn’t do it, he sort of couches it by saying, “I didn’t know how serious it was.” And Phonte himself in one of these Zooms was like, “You know what? Fuck that shit. I didn’t call him, that’s what it was. I don’t need to protect myself here, I was wrong. Cut that part out.” So we cut that part out, and it’s a much stronger movie for it. But that ethos, I think, carried through from beginning to end where they’re self-aware about what was going to make this a better film.

Yoh: One of my favorite aspects of working with them on this film was Phonte and Pooh were very instrumental in setting up all the interviews, but they weren’t present for any of the interviews. They didn’t stay in the room with us and [talk over] our shoulders like, “Tell them I’m great. Tell them I’m amazing.” They removed themselves every time. And I think that opened up for everyone that we interviewed to be open and vulnerable about the Little Brother story, or about who Phonte is, or about who Pooh is.

Both of the guys referenced being intentional about choosing to collaborate with filmmakers who are younger and didn’t experience their rise in real-time because they felt like the cross-generational aspect would be a better collaborative experience. How did that dynamic benefit your storytelling?
Yoh: You don’t come in with starry eyes, you don’t want to hunker on some of the more fan-orientated aspects of it. A small anecdote is when we were doing the LA screening, we had a young woman come up to us, and she was just so enthused about this Phonte podcast that me and Holland never heard of before. She was just riffing about how great this one moment was of this podcast that he used to do, and we had no idea what she was talking about.

When you’re only coming in thinking about the story and not thinking about being a fan, then you end up getting a truer story. It’s not a fanfare or a specialty doc that’s only going to relate to the stans. This is something where we’re really trying to touch on a universal point about brotherhood and about coming of age in a very specific way that doesn’t include all of the nuances of how the song was made or being in a studio during this time or Percy Miracles.

One of my favorite aspects of the documentary is the emotional variance. How much of the film’s cut process was about making sure that a good emotional balance was on display?
Gallagher: I think the tonal North Star is that we wanted to make it feel like a Little Brother album. Phonte pointed out the Frank Zappa doc of all docs, and he was like, “I’m not a Zappa fan at all, but this doc just feels like his music.” And he thought that was so dope. We decided early on that we wanted it to feel like a Little Brother album. And so what does that mean? It means you’re going to have these moments of levity. You’re going to have these moments of poignancy. So you’re going to have skits. There’s a direct analog with the animated bits, those are basically the skits in a Little Brother album, that’s the animated bits. Someone at one of the Q&As said, “I feel like I’ve just got another Little Brother album,” and that was the biggest compliment for us as the filmmakers because that’s what we were going for really.

What projects are y’all working on in the future, and what did you learn from crafting this documentary that you’ll take into future work?
Gallagher: I think Yoh and I have been figuring out what it is with Rap Portraits, generally. We want to tell rap stories, obviously, in the documentary form, but I think honing in on a certain style is what we’ve been trying to do. And yeah, we want to tell these big important rap stories. We think these long-form movies, and that’s the world that we want to live in. A lot of the stuff we learned on the doc is related to the marathon aspect of it and how it’s a huge task to do this stuff, especially when you’re doing so many of the parts in-house.

Yoh: To piggyback off of that, I feel like what I learned is that it’s a real privilege being able to pull up on people and be like, “Tell me your story,” or, “Tell me what you know about this culturally relevant group or art,” and be able to get the dimensions of it. You’re never going to get the whole thing from one person. Being able to talk to 30 people about one specific thing is so insane because everyone has a different vantage point. I love the idea of just interviewing one person. But, man, being able to interview 20 people about one thing, that’s a whole different ballpark. It reminds me of oral histories, being able to pass down stories in a vintage kind of way.

I think being unexpected is what I love about Rap Portraits. I feel like everything we’ve done so far has been a little unexpected. If you watch Hype, or if you’ve read my interviews at DJBooth, you might not be thinking we’re making documentaries in the next X amount of time. But that’s what we’re doing right now. And I think what we do in the future is going to continue to be unexpected. I hope that the stories that we tell in the future, you’re like, “Oh, I can’t believe they got that person,” or, “I can’t believe they’re working with these people.” I was at Olive Garden before DJBooth. And now I just did [a Little Brother documentary]. It doesn’t make sense.

Gallagher: The symbiotic relationship of making documentaries and doing journalism is that you’re being granted access into a person’s life. What I’m proud of with this documentary is [we took that] really seriously. You have to take that responsibility of the access that you’re granted seriously by taking the story seriously, and in good faith trying to make something grand out of it.

I think that a lot of what we do with Rap Portraits is trying to take the everyday world of being an aspiring rapper or a rapper with a story behind them and elevate it into this grandiose play. The stories mean a lot to us, and we really care about what we’re doing and are grateful to have the ability to do it.

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