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Little Brother Has Come a Long Way From the Okayplayer Boards

Beloved rap group Little Brother released their debut album The Listening 20 years ago. Rappers Phonte and Big Pooh, along with producer 9th Wonder, delivered a critically acclaimed project influenced by traditional hip-hop production techniques, soulful samples, and an emphasis on lyricism that was in complete opposition to not only rap music coming out of their North Carolina home state, but Southern rap music as a whole.

The Listening came about during the early 2000s, as the internet became a space for people to talk about music with each other. Little Brother found camaraderie — and feedback for early tracks and The Listening (whether they wanted it or not) — and built a fanbase for themselves thanks to their participation on Okayplayer. A place where fans could engage directly with artists, Little Brother’s active involvement on the platform allowed their music to expand beyond Durham, NC, foreshadowing how the internet could and would play a crucial part in an artist’s rise in the digital age.

Fast-forward and each member has found success carving their own lane and putting on for North Carolina rap. 9th has since become a Grammy-nominated producer and the genius behind Jamla Records, the home of fellow North Carolinian Rapsody. Phonte has established himself as a rapper, singer and composer, having done everything from pop up on Kaytranada tracks to earning a Grammy nomination with The Foreign Exchange, his soul duo with Dutch producer Nicolay (the two actually found each other through the Okayplayer message boards). Big Pooh serves as a manager for Dreamville signee Lute, and has released a series of impressive solo projects.

To commemorate 20 years of The Listening, Phonte and Pooh are leading an event called Made in Durham: A Little Brother Block Party. Hosted by Sam Jay, the hip-hop legends will be supported by Big K.R.I.T. and The Cool Kids, and will also feature Zo! & Tall Black Guy, DJ Hourglass, and DJ Wally Sparks.

Ahead of the event, Little Brother spoke with Okayplayer on Zoom about their early days on the Okayplayer message boards, recording The Listening, their relationship with De La Soul, doing their Gangsta Grillz tape after the fallout of The Minstrel Show, and more.

To commemorate 20 years of ‘The Listening,’ Little Brother are leading an event called Made in Durham: A Little Brother Block Party.Photo by Antoine Lyers.

The interview below has been edited and condensed for length and clarity.

You both were active on the Okayplayer boards in the early days. Can you share what those moments were like?

Phonte: It really was Black Twitter before Black Twitter. Okayplayer was patient zero for what we now know as social media. I was the one that was on it more than Pooh or 9th. We would be on there talking about music, a lot of times arguing about music. There were a lot of fights, arguing — but there was also a lot of creativity. We met a lot of people that are still a part of our journey to this day.

I remember those early days of making records and putting them online and it was like, “Yo, if this ain’t right, we’re gonna hear about it. The Player gon’ tell us.” The message boards didn’t care about nothing. If your shit was wack, motherfuckers would let you know immediately.

Did y’all get negative feedback?

Pooh: I got plenty. I definitely want to thank Okayplayer for the motivation, because I got plenty of negative feedback when we put The Listening out.

When you reflect on the past 20 years, did y’all ever consider that your influence would be as big as it is today?

Phonte: No, not all. I think we were just trying to make something that we liked, something that we were proud of. We never would have guessed that 20 years later, we’d be having a block party in our hometown. Looking back over the last 20 years from where we started to where we are now, it’s a very humbling feeling.

Pooh: It’s one of those things where when you are starting out as a new artist, your only goal is to make it. You’re not really thinking down the line. We weren’t even thinking a year ahead, let alone 20. We just wanted to make the best music we could at the moment and see what it could do. So, to be here 20 years later and still have relevance — still be, you know, “In fighting shape” as Phonte likes to say — still have people that care, and to still be celebrated, is definitely something that you don’t take for granted.

What is your fondest memory of recording The Listening?

Phonte: When we started The Listening, I was working my first “real job” fresh out of college, and I would go to the studio after work to record. I remember being at work thinking, “I can’t do this. This can’t be my life.” You know, going to work, coming home, going to sleep, waking up, going to work, coming home. I was like, “Yeah, I’m not doing that.” The thing I was most excited about at the end of every day was leaving work and going to the studio to record. So, my mentality was, “For the rest of my life, I only want to do the thing that I’m excited about doing.” That’s what led me to write “Speed.”

Shortly after, I quit my job and decided to pursue music full time. I’m only interested in doing things that I’m really passionate about.

Pooh: Recording The Listening was like an age of discovery. For us, even though we had chemistry, we were still figuring each other out creatively. I think we were all learning. Learning how to put together an album, learning what we liked, learning what we didn’t like, and just going for it. We were fortunate that a lot of it worked out the way it did. I was the youngest and a novice, so I probably had the most to learn. There were no less than four or five people in the room every time we recorded. In between recordings, we would talk about music, life, sports, and girls. What I remember the most about working on that project specifically, were those in between sessions conversations.

The Listening: The Story Behind Little Brother’s Debut

On The Listening, you describe hip-hop as a culture in a state of decay. Has your perspective on hip-hop changed since then?

Phonte: I think our perception has changed as the culture has changed. 20 years ago, seeing rappers in their 40s and 50s still continuing to create and release compelling music, there wasn’t really a model for that. Rap was always considered a young man’s game and that’s not necessarily true anymore. Nas is still putting out records 30 years into his career. That was just something that we didn’t really have a model for at that time. So, I think how our view of hip-hop changed was that we began to understand how it’s possible to age gracefully in hip-hop, while still being able to meet your audience and serve them.

Pooh: As you grow, your perception should change. I think for us, we’ve had the fortunate thing of our audience growing with us.

De La Soul is one of your main influences. This year was bittersweet for them because they finally got their catalog on streaming, but Trugoy also passed. What was it like for you as a fan having to experience that, and what did Trugoy mean to you?

Pooh: I definitely was excited for them, and like you said it was a bittersweet moment, especially for me because Dave passed away on my birthday. Fortunately, I have formed a relationship with De La Soul. It still blows my mind that I can text Posdnuos or Maseo. I knew that their catalog would finally be available on streaming services before Dave passed, and I was just happy for them. You’re seeing an iconic group that influenced us get their art back and be able to control their destiny. That’s a major accomplishment. I’m not sure people understand how big of a deal it really is.

Phonte: Getting old is expensive, so to see those brothers get control of their catalog at this point in their lives is a blessing. I love to see our veteran artists reclaiming their catalogs and being able to eat off their work years later. It’s really important.

I think about that often because Pooh and I, we did the same thing. With the exception of The Minstrel Show, we were able to get control of our back catalog. Us having it now, 20 years later, we have a greater understanding of what it is and how to monetize it.

The music industry has a history of being exploitative toward young artists. If you could tell your younger selves one lesson that they should remember, what would that be?

Pooh: Believe in yourself is what I would say to my younger self. That applies to business decisions as well, not just the art of rap. My advice to myself would be to bet on yourself. Your understanding of what you are doing is better than you think.

Phonte: In the words of my brother Black Milk, ain’t nobody coming down to save you. I think when you’re younger and coming up, you kind of look for the magic wand in labels and managers. You have that thought in your mind like, “ I know I’m doing OK but if I could get with this person or this label, if I could sign with this person, then that’ll take me to the table.” A lot of times that may not be the case. As an artist, you really have to be the visionary for your career. You can be signed to the biggest label, have the most powerful manager, and the biggest lawyer. But if you don’t know who you are, where you want to go, and who you want to be, then none of that shit matters.

At 25, when we signed to a label, I was just like, “Yeah, they know what they’re doing.” But once we got on the inside, we realized that they were just making shit up as they went along, too. In hindsight, I would just tell myself there is no magic wand, there is no savior. Save yourself.

No Wish (feat. Phonte & Raphael Saadiq)

Speaking of Black Milk, Phonte, you contributed a standout verse on Black Milk’s “No Wish,” that tackled a very sensitive but necessary topic. Did Kendrick’s “Mother I Sober” happen to inspire you at all for that verse?

Phonte: No, I was just telling my story. That was my first verse written in 2023. Because we were busy working on the doc and the business of LB, I hadn’t written anything in a while. He sent me the track and that was just some of the things I’d been working through at the time, so I put it on the record.

Can you imagine doing another LB album with one producer? And if so, who would that be?

Phonte and Pooh: I don’t think we’d do it again.

Pooh: That would be tough. With Little Brother you have to satisfy two people. We both know where the line to compromise is, but if you hear what he gets for him and then what I get for me, it’s night and day. I think for us, having one producer wouldn’t get us to where we need to be, or it would take a very long time.

Phonte: The person that I think we both mutually trust is Focus. When we worked on May the Lord Watch, he produced ”Black Magic” and “Good Morning Sunshine,” and we’ve done countless other records prior to that. We call him the LB whisperer because he gets it. He’s worked with us individually as solo artists and as a group. So, he is one of the few people who understands the spectrum of me versus Little Brother versus just Pooh. If we were to do that again, it would definitely be Focus.

Would or have you tried to do another 9th-produced project?

Phonte and Pooh: No.

Phonte: We talk about it in our documentary May The Lord Watch. When the doc comes out, it’ll clear the air.

Made in Durham: A Little Brother Block Party is less than a month away. What are y’all most excited about?

Pooh: I’m really looking forward to being back in Durham. We view Durham as an honorary group member. I’m looking forward to being in the place where it all started. This is the perfect opportunity for us to not only celebrate Little Brother, but also celebrate the city of Durham. The best part is we get to celebrate with our city and thousands of people who have probably never been to Durham a day in their life.

Phonte: I’m just mainly looking forward to the fellowship. Having all of our people in one space. With losing Dave [Trugoy] and losing Phife [Dawg] a couple of years ago, I think it becomes more important for us to celebrate each other. For me, the block party represents a celebration of hip-hop, Little Brother, Durham, and life. It almost feels like a family reunion.

Little Brother ft. Lil Wayne- Breakin’ My

A notable but often undiscussed moment for y’all is that you got a Lil Wayne feature arguably at his most prolific for Getback. How did that come about and do you remember how y’all felt learning that Wayne was a fan?

Pooh: We met Wayne a year prior at Allstar Weekend in Houston. We were all at the radio station. They were running artists in and out doing interviews, and Wayne happened to go in for his interview before we did. He actually said our name while he was doing his interview. When he came out, we introduced ourselves and he told us he was a fan.

While we were working on Getback and that particular track came up, I was like, “Yo, Wayne gotta be on this.” He was on tour at the time and he was like, “Yo, if I don’t get a chance to slide through when I leave North Carolina, give me a week. I’ll be back in Miami and I’ll get it done.” He sent the track back less than a week later with vocals, stems, everything.

Phonte: It was very professional.

Pooh: I’ve always been a fan of Wayne and I tell people all the time ‘til this day, he’ll always have my respect for that. He was at the height of his career and he didn’t have to do that at all. The fact that he did it and did it in a timely manner is admirable.

Amid Gangsta Grillz having a resurgence with Tyler, the Creator’s Call Me If You Get Lost, fans have revisited some of DJ Drama’s previous tapes, including yours with him. What led to y’all wanting to do one, especially considering most were done with more trap-leaning and mainstream rappers?

Phonte:Separate but Equal, that was ‘06. We had finished The Minstrel Show and we met Dram at Apache Cafe. We were doing a show in Atlanta. I knew Dram from his earlier tapes like the Afromentals, and his early stuff that was really leaning heavy on the underground hip-hop and neo-soul vibes. A lot of people don’t realize but Dram is a music head just like us. We talked to him about doing a tape and he was like, “Word, let’s do it.”

For us, it didn’t make sense to write new rhymes just to spit over old beats. I’m like, “Why am I wasting time writing new verses to spit over old beats or other people’s instrumentals, when I can just put those new raps over new beats and it just be a whole new song?” That approach was more interesting in my opinion. When we went in to record, we treated it like we were making another record. At that time, DJ Drama was doing tapes for Wayne, Jeezy and Tip. So, our mentality going in was, “Yo, we gotta come with it.” Also, I think we were both really frustrated with the fallout of The Minstrel Show, so we just went in and did us. We were like, “We just gon’ fucking rap.” And that’s how the tape came about.

Let It Go – Little Brother and DJ Drama Featuring Mos

With the energy Phonte just described, did y’all feel like y’all had something to prove?

Pooh: I don’t know if it was more something to prove, or more of our frustration with how The Minstrel Show played out. We just had a ball of energy and we put it all into Gangsta Grillz. We also understood what the moment meant and what the importance of Gangsta Grillz was. It was the perfect storm for us to go in there and, as the young boys say, “Pull the chopper out and do what we do.” It was also the first time where — even though we had little skits in there because that’s what we do — the Gangsta Grillz project was the first time we didn’t have a concept. We were just in their rapping. I think people got to see a different side of Little Brother.

Besides celebrating 20 years of The Listening with the block party, what’s next for Little Brother? When can we hear a new project?

Pooh: Shit, the next project is going to be this Little Brother documentary. I know for a lot of people their introduction to Little Brother was an album, and we definitely see a lot of people asking for it. But we want people to understand that while we always work on music, we definitely have other things that we’re developing. When you see us together, you see Little Brother. The documentary, block party, us working on another artist’s album — whatever it is, you see Little Brother. It’s just not always going to be in the format that fans were introduced to Little Brother.

You gotta make time for sitting down and doing music, and it’s tough when you’re curating a block party and producing a documentary. We’re doing it all. It’s not like we went out and hired a production company, and they’re taking care of it and we can just check in to review footage. We are in the trenches with both of these projects and it’s a lot of detail.

Going to a show or festival and just pulling up to rap, versus putting on a block party — two total different things. Interviewing for a documentary versus actually being on the production side — two different things. So, we are working. It’s not always the creative format people may want but we are working. And, of course, we look forward to seeing all of our supporters, old and new, pull up on us in Durham on October 7.

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