De’Wayne Jackson Is Not Afraid: An Interview With The Soulful Rapper

Turning down the Southern Playalistic sounds of Outkast blaring through the car’s speakers, De’Wayne Jackson answered a phone call from a friend he was supposed to unite with over the weekend. “Man, I just got done with a photo shoot and interview, then tomorrow I have a studio session and a full day… I promise we’ll hang out soon!” he explained to the person on the other end of the phone as we neared his house in North Hollywood, California. “I’m not famous!” He laughingly pleaded to his friend.  

Two years ago, De’Wayne Jackson left his family’s home in Spring, Texas and ran away to the West Coast. Los Angeles held a new set of challenges for the musician, but he didn’t hesitate to uproot himself, not even for a second. Driven by an insatiable desire to pursue a career as a rapper and singer, De’Wayne spent his first days in Los Angeles consumed by two non-music related jobs in hopes of someday being able to quit and focus on the music.

Photo by Emily Berkey

Two years later, De’Wayne is asking his managers at his very part time job for days off so he can attend business meetings, studio sessions, press runs, and back-yard barbecues with Joel and Benji Madden, the owners of the management company he’s signed to. His friends are teasing him about being famous, but his southern roots are still strong. His tireless faith in himself, God, and his by-any-means-necessary work ethic has paid off.

As we entered a quaint coffee shop in Studio City, California, De’Wayne held open the door for a group of older women, “after you,” he kindly insisted. De’Wayne drank from his cold brew coffee and took a seat, giggling to himself. “It’s happening. I’m so glad to be here,” he lamented as we began the interview. De’Wayne opened up about the recent release of his Don’t Be Afraid EP, the roots of his soulful sound, and why he’s unapologetically baring it all and turning his journal entries into songs.

Emily: You’re from Spring, Texas, a town of about 50,000 people just outside of Houston. You were raised in a traditional Baptist family with a stepfather who’s a preacher and you sang in the choir until you were 17.

De’Wayne: I did.

That was only four years ago! But you originally set out to be a rapper when you started doing music. Why and when did you decide to allow the worlds of rap and religion to mesh together?

When I started doing music they just came together. It was just, it was what came out of me. It was a lot of gospel but it was also a lot of rapping and Kendrick Lamar and J. Cole, but the Christian in me and the gospel and my stepfather being a preacher and us being at the church three days out of the week. It was a combination of me being a big person with faith and me also being a rebel and it just really made sense. I have a lot of soul in my music and I feel a lot of that comes from me being a church boy [laughs]… It’s a big part of that.

On this EP you rap “I’ve been getting on my knees/looking to the man upstairs,” tell me about your relationship with God and how it impacts your life and music.

Oh my gosh. I have a relationship with God. I don’t know if it’s the best one, but I have so much faith and that’s the reason I’m out here. That’s the reason I took a leap of faith because I do believe in God. It has a lot to do with my music and it has a lot to do with being out here because it’s the only thing I can believe in. I mean, I believe in myself too, but it’s also about believing in God when I do my music. Nobody told me to do it but I always believed from when I was younger that I could make it happen.

When you first told your parents you wanted to do music at age 14 they were anti.

They were very anti.

Dewayne Jackson for Rehab Online Magazine

Have they come around?

They have. My parents, they were very anti until about last year. My biggest dream when I was in high school, all I wanted my mom to do was post my songs on her Facebook and she would never do it. Now she loves it and she inspires me and she pushes me and she’s like ‘Give the people your voice’. She came out to LA last month and surprised me, that was really beautiful, and I got to take her to the studios and show her what I’ve been doing and she’s really proud. She reads every article that’s posted. It’s amazing…it’s amazing.  

Does she post your songs on her Facebook now?

She posts them on her Facebook. It gives me the biggest smile, it really does. That was all I ever wanted. That was all I ever wanted, seriously. It means a lot to me that she sees the work that I put in and it was worth it. When I came out to LA, it was the first thing she let me do on my own. I was like, ‘Mom I’m going to make this happen’ and she was like ‘okay’. She really understood. For some reason, that time, when it was the craziest thing I was doing, she understood and let me run. Moms know. They really do know.

If you have your parents support, nothing else matters.

It really doesn’t, man. I love her. I’m her only son.

You’re signed to MDDN, an artist management company founded by Joel and Benji Madden. Tell me about how that came about. Also, you’re the only rapper on their roster. How do you think that works to your advantage?

First off, I love them. I freak out every time I’m talking to Joel and Benji. My manager, Naveed, was working at MDDN. They interviewed Naveed and he showed them my music and they wanted to sign me from day one but we let it build and let me grow as an artist for a couple of months until they really wanted to sign me…but that’s how it came about. My manager started working there and I was one of his artists and they wanted to bring me on board. It’s been a blessing. They’ve been helping me a lot. But being the only rapper at a Rock management company has been great. I’m a little different from everybody else and I don’t mind that at all. Everybody else is doing Rock and Punk Rock and I’m doing Rap Rock. It blends well, it’s cool.

Is that what you would call your music, Rap Rock?

I’d call it Alternative Rap. I don’t like to say genres, but it’s a bit alternative. I’m not just doing one thing…There’s no way you can say it’s just rapping.

I’ve been following you for a hot minute. I once knew you as De’wayne Wavy. Why have you chosen to use your full legal name as your rap name?

[Laughs] Because that was so silly [laughs]…I’m so ashamed that was my rap name. My cousin gave me that name on Twitter and I just stuck with it. But then I was 19 and I was like ugh ‘I just want to go by my own name’. I love just being true to the art and being true to the people who are listening to my music and being true to myself, most importantly. I think De’Wayne Jackson, just going with the real name, just helped me tell my own stories. I don’t want to be the artist that’s telling other stories, and that’s cool for people to do that, but I really want to give my own experiences and give my own life to people. That’s why I chose to go by De’Wayne Jackson.

Your song and project titles include It’s Ok To Not Be Ok and your most recent, Don’t Be Afraid EP with tracks like “Therapy” and “Truth Is” they almost come across as notes to self. Is that safe to say?

Aw man! It’s so safe to say. My music is like therapy to myself, it really is. I need it. I really need to get these stories out of me and make music or I’d go crazy if I didn’t do it. It really is notes to myself and me trying to continue to learn myself as I continue to grow up and become a man. This experience has only allowed me to tell stories like this… I literally have to. It’s crazy. I’m constantly trying to learn and trying to better myself and trying to really become the most beautiful person I can be, and I’m not there yet. My lyrics help me and writing them out helps me a lot to continue trying and pushing.

You’re really vulnerable in your music. You once said that you’ve had reservations about your mom hearing certain tracks. On “Coming Back Home” you spit a verse and then lament, “I never told my mama that/I never told nobody that.” What drives you to be so raw and vulnerable in your music?

[Laughs] I’m honored that you know that. I have to. I have to say what’s real, man. I never really told my mom…I pretty much, when I came out to LA I told my mom kind of a white lie. I was like ‘Mom, I know people out in LA that will be able to help me and I got a job out there.’ I didn’t really… but I had so much faith in it.

Did you know people out here and did you have a job out here?

I did have a job and I knew one person who wasn’t going to be helping me like I told my mom she would be. I feel like I kinda ran away to a place that wasn’t safe but I just had to do it.

What drives you to be that raw and vulnerable in your music. You’re admitting you never told your mom something but you’re putting it on a track.

I want to let them know through the music. The music is my only safe place to tell the truth. I’m really not good with talking to people face to face and letting them know how I feel, but In the music and when I write it in my room alone you feel like nobody will ever hear it. So it really allows you to be free and truthful. And like I said, I love being honest, man, and I have to be honest with my music because it’s the only thing that’s ever made me feel free. So I can’t really be on songs lying and saying what’s not true, man, I can’t do it. When you’re alone in your room and you’re writing and it feels right you’re not really thinking like, ‘Oh my mom’s gonna hear this’ but once it’s out I’m like oh my gosh, she’s going to call me.

I wouldn’t be so much worried about your mom hearing the line about your second thoughts regarding your move to LA. I’d be concerned with her hearing a track like “Truth Is”… it’s really explicit.

[Laughs] That’s the worst thing I’ve ever said on a song. It’s the worst thing I’ve ever said and I definitely got a call about that from an ex friend.

Dewayne Jackson for Rehab Online Magazine 2

Did they know it was about them and they were concerned?

Yes. The whole song was about her and I have her name tattooed on my chest. It’s the only girl I’ve been with in my life. I went back home to Houston from LA and she was acting like she didn’t know me. She was acting like we weren’t together for like seven years. I came back to LA and I wrote that song. She was trying to throw shade at me. I didn’t like that [laughs]

That track, “Truth Is” is basically an open letter to a past lover that you’re sharing with the world. You also chose to shoot one of your recent videos at your Grandma’s house and include family in the shoot. Do you ever worry about blending your work and your personal life? Is there a line?

There’s NO line. My personal life is my music. It’s nothing where I’m like ‘ok I’m going to turn this off and I’m going to become this other thing’. My experiences, I have to write about them because they’re my own experiences. About going back home and shooting that video at my grandmother’s house, it meant the world to me. I got to get my sisters and my brothers in the video and my cousins and my dad… It was beautiful. I always wanted that neighborhood to love me and to know that’s where I’m from and to know that’s where I grew up… To go back there and shoot with those kids, it was special.

I can tell you have a strong moral compass, and this desire to be a good role model. In one of your songs you say, “I want to be the one they look up to.” Where does that come from? Growing up, did you have someone to look up to like that?

No. I always wanted that and the music artists I listened to were that for me. Growing up where I grew up, everyone was really close-minded and nobody told you to go out and get it. It was like ‘ok you do this step, you do this step, you do that step and that’s it, that’s your life’ and that’s totally fine but there are kids out there with big dreams and they want to support their family in another way other than just working and going to college. I want kids to be open to experiencing life and going for their dreams. Even though it sounds cliché, we only get this life one time. I want to be the one to tell kids to go out and get off the porch and go live their dreams and go try for it. You don’t get it again. I want to be the one, if nobody else is going to be the one, I’ll be the one to tell them because I didn’t have that.

On the track titled “Coming Back Home” you say “I hate I ran away from home.” are you talking about your move to LA?

Yeah, just running away from fear and running away from past love and running away from being scared of failure. I wasn’t going to school, the girl that I was talking to wanted me to go to a community college with her just because I was at home working on music. And I ran from that. It wasn’t like I ran away and didn’t tell anybody, but I ran away from the problems I was facing at home to come to a whole new problem, but I knew I had to come. I was riding around, working for my job, and I was driving paint around and I was like like, ‘yo I’m leaving I’m leaving next week’ and I called the bosses here and I came.

How has your idea of “home” changed since being in LA?

I don’t think it’s changed much. I feel like LA is my home now because I stay here. But maybe not. Spring is still home for me. I don’t think it’s changed much. I still want to be able to go back there and live eventually. I’m just working now. I have something I have to pursue and I have to get done. My idea of home hasn’t really changed. I’m still so inspired by everything that comes out of Texas and that’s where all of my stories are from and my family and growing up there… Man, it taught me so much.

When you first came to LA you were working two jobs at Sherwin Williams and T-bell. It’s hard to get by in LA and often times artists, like you did, have to take on work they don’t want so they can be in the city they know they’re supposed to be in. If I understand right, you’re still working a job unrelated to music. Tell me why you continuously choose to stay here despite having to work so hard just to stay here.

First off, that’s what I came out here for, and I’m not a quitter. I would never quit. At all. That’s the only way I see me failing is if I do quit. I know I’m getting closer to my dreams every day. I’m starting to see them, and I really feel that. It doesn’t scare me to have to work and to have to sacrifice and to just have to work a regular job. It doesn’t really like, I’m ok with it, I know I have to be here to pursue my dreams and to try to get there, so I can’t leave.

You just dropped and EP. Is it a prelude to an album? A precursor to a tour?

Definitely hopping on a tour hopefully by the end of this summer… I’ll probably be going on tour along with someone this year and I’m definitely working on an album. For sure.

Can you tell me who you’ll be going on tour with? Someone on the MDDN roster?

I don’t think I can say that yet.


All photos shot by Emily Berkey for REHAB. 

Connect with De’Wayne Jackson:

Instagram | Twitter | Soundcloud | Spotify

Emily Berkey

Emily Berkey is a freelance journalist and film photographer currently based in Los Angeles by way of Portland, Oregon. A few of her favorite things include: sitting down for intimate conversations, unedited photo shoots, and helping artists share their stories.