Chicago’s Jayaire Woods Isn’t Afraid of Pain

“I want to show people the real instead of bravado or acting like nothing hurts.”
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“I have learned now that while those who speak about one’s miseries usually hurt, those who keep silence hurt even more.”—C.S. Lewis

The idea of processing pain is so integral to 25-year-old Chicago rapper Jayaire Woods’ music that his songs feel like he’s kneeling in church, taking confession. “Lost my brother yesterday / tears dried on my shirt,” he concedes on “Wood;” his slurred vocals—which sit somewhere between the emo-rap theatrics of the late Juice WRLD and the gruff gangster melancholy of Scarface—suggest the pain from this loss is still inescapably raw.

On his criminally underrated Big Wood EP, released independently in 2017, Woods’ dejected vocals gain more color as each song progresses. Standout “BIG” shifts from Woods solemnly rapping to cathartically howling into the microphone with an emotional clarity reminiscent of a young Kid Cudi—another artist aware of the power of balancing rap with singing the blues.

“I want my music to teach young Black men how to be men and how to heal,” Woods says during our late-night phone call, where no topic is off-limits. “I’ve always tried to rap about things I am not comfortable talking about in real life, where I’m much more quiet and introverted. Rap is about clearing the skeletons out of my closet. I hope that by dealing with my own pain [on wax], I can help other people deal with theirs too. Staying silent or bottling up your emotions is never a good thing.”

Woods’ latest album, Life is Grand, released earlier this year, displays clear artistic growth. For one, Woods sounds like he’s starting to let more light back into his life. “Before, I was still tortured about what happened in my past,” he says, confirming my suspicions, “but Life is Grand was about finding a way to look back warmly [on it all] and get a smile back on my face.”

Lead single “Jayairemax ’98” has a bouncy melodic sensibility, with Woods triumphantly rapping, “I’m gonna live forever through these words.” He makes a convincing case for being one of hip-hop’s next big stars. As you listen to the artist long for the innocence of his youth on urgent anthems like “Now or Never” and the even more nostalgic “Recess / Detention,” there’s a nagging sense you’re listening to a special act. Woods already possesses an emotional clarity some artists spend a whole career discovering.

DJBooth caught up with Jayaire Woods to reflect on his unique melodic rapping style, what he learned from his experiences on Quality Control Music, and why the 2020s might finally be the moment the world wakes up to his stirring music. Our conversation, lightly edited for content and clarity, follows below.

DJBooth: What made you want to be a rapper?

Jayaire Woods: I grew up in a small suburb just outside Chicago, called Bellwood. It isn’t super poverty-stricken, but it’s motivated by gang activity. It’s the kind of place you could choose to be a nerd or a gangster, you have those options, but the allure is always there to go to a darker place. Making music was something I did when I felt some type of negative way. I rapped about things I wasn’t comfortable talking about in real life, and it made me feel better. The microphone booth was like being face-to-face with my therapist. Rapping made me feel braver. Nas was probably the artist who made me want to rap. I just loved how vivid he could be in describing what was inside his chest.

Young men are often scared to talk about their feelings, but that’s definitely not you, is it?

I want to show people the real instead of bravado or acting like nothing hurts. My music is like a road map to dealing with pain, but it’s also made to make you dance and have fun, too. It’s about showing all the different sides of being young and Black. For all the introspective tracks, there’s swag songs too. I can do absolutely anything.


On “Knowbody,” you talk about falling out with friends who are annoyed that you’re persisting with a rap career and not getting a regular 9-to-5. What gives you the motivation to keep on pushing?

Being an artist isn’t all it’s cracked up to be. Sometimes I am so focused on my craft and improving as an artist, pushing out like three to four songs a day, that I don’t take proper care of relationships with my friends or family. “Knowbody” is giving you a window into those kinds of pressures. I will never quit making music, even if I don’t gain the popularity I feel [I] deserve. Giving up is not a thing I can even entertain. I have hope that music that comes from the heart will always find an audience, eventually. I also learned from my mother that if you want to make something happen, you need to do it yourself.

What did you learn from your experience with Quality Control?

I had a great time and gained a lot of experience. We toured, and I saw a lot of shows. I was kind of like a bench player. I watched Yachty in his heyday; got to see Migos. The biggest thing I learned [from them] was to stay consistent and be on the pace. Once it is your turn, you have to be able to do it every day and be switched on at all times. These guys did like a show a day. It was crazy, bro. My music is so rooted in nostalgia that it just didn’t fit with the Quality Control blueprint. It was a shame, but I don’t hold any grudges. It just wasn’t the right match.

That nostalgia you speak of seems to rest on this double-edged sword; sometimes, it’s warm and fuzzy, but other times it’s rooted in self-destructive grief. You bravely talk about drinking too much to cope. Where does all that come from?

I’ve learned that we can go at any time. I’ve had aunties and uncles die, which was more expected, but when you lose friends who are your age to the streets, that’s a completely different inspiration. Any of us can go at any time, and I try to keep my lost ones with me, always. They tell me how to feel. Their spirits guide me. I look to them for guidance, and that’s why the pain you hear on my records feels so deep.

I love “Bag of Tricks.” That haunting piano sample reminded me of JAY-Z’s “Dead Presidents.” The lyric, “I lost my mind, but never my swag,” speaks to the endurance of Black people and this idea that they must maintain their cool even in dark situations. Was that the idea?

Yeah, that’s pretty accurate. You can never lose your cool in this shit, bro! You can lose everything else but never lose your confidence. Life keeps moving, and if you’re sitting there feeling sorry for yourself, then you’re gonna get nowhere. I’m built to endure, trust me.

For people who have never checked out a Jayaire Woods project, why should they?

If you wanna hear a real story about an authentic come-up, then that’s me. Historically, rap is based on the streets and sharing your journal of being present in that environment; that’s why Illmatic still sounds so perfect. I want to do that, too. I’m a person who doesn’t have it all figured out emotionally, but people can see I’m not afraid to admit that or show my imperfections. I don’t want to be a superstar; I just want to gain an audience big enough to let me make music with full creative control. World tours would be nice, too. I’m not going to stop until that happens.

Listen to Jayaire Woods on Audiomack.



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