WontoWatch: Jayaire Woods

No one knew he made music. His first release ever is a song about heartbreak, and it makes sense that after years of writing and creating and trying to find the right way to start his (public) musical journey, something finally clicked. The record is called “toolong.”, and it is special. The meaning, the melodies, the rawness. It’s a song that captured my attention instantly, but once I found out this was Jayaire Woods’ debut track my intrigue levels went through the roof. I had to find out more. I had to hear his story.

Woods had been writing poetry since he was in the 1st grade, but he never expressed his thoughts and passion for music outside of his own head until 2 short months ago. The powerfully smooth “toolong.” was his introduction to the music scene – for us, as well as his loved ones. No one knew he made music. Jayaire told me the story of how his mom and sisters reacted the first time they heard the record, it gave me chills. We also touched on the impact of his hometown of Chicago, details on his upcoming debut project, and the importance of finding balance in life. Jayaire Woods is undoubtedly WontoWatch. Read the full interview below.


AllWon: How old are you?

Woods: 20 years old.

AllWon: Hometown?

Woods: I’m from Chicago – West suburb called Bellwood, about 10-20 min from the city.

AllWon: How did you get into music? When did you decide this is something you wanted to really do?

Woods: I’ve been writing since like, 1st grade, I’ve been writing poems.. 4th grade I started writing raps. And then maybe when I was a sophomore I realized I wasn’t going to the NBA – I had real big basketball dreams, and I was really good too.. but I’m 5’8, kinda too short for that shit. So around sophomore year I started to take things really serious. But I just started really rapping out loud, I just started being in the studio a year ago, I’m new to all this shit, but I’ve been taking it seriously for a long time. I’d say around the 8th grade when I realized I’m good at this, and that I need to keep practicing type of thing…

AllWon: On that comeup, throughout that journey, were their any influences? Was music something that was in your household? Did you pick it up by yourself…?

Woods: That’s the weird thing. My mom hates rap, my pops isn’t big on music either.. I have two sisters, they like music but they’re into like, Beyonce [laughs]. So it was mostly me – I can’t think of a person that influenced me to do this. I’m just a real big fan of music, and writing was always my shit, so it kinda came by myself internally.

AllWon: That’s cool, man. Sometimes you need that personal experience to bring that stuff out of you. There must’ve been some artists you were listening to around that time that got you into music, hip-hop and the whole scene…

Woods: The first hip-hop album I bought was in the 4th grade, It was MA$E’s Welcome Back CD. It’s been a little bit of everybody after that. I was big on Nas when I was first starting to take hip-hop serious… then J. Cole came out, that’s still my favourite rapper today. Then Kendrick came out. It’s mainly been those two, Kendrick and J. Cole – they helped me a lot with this shit. But before that it was more Nas… Illmatic changed my life.

AllWon: Getting back to Chicago – It’s truly been an amazing run for Chicago artists in the past few years. Not to say Chi hasn’t always been home to great artists of course… But how has you know, the whole drill movement, seeing guys like Chance [The Rapper] and Vic Mensa doing what theyre doing… has that helped motivate you? Being from the same city as these guys…

Woods: I remember when Chief Keef first came out, I was a senior in High School and he changed everybody’s mentality. All my friends are Chief Keef influenced, I’m more so on the other side of it, but a lot of my friends are into the drill scene, and now everybody raps on that side. But with Chance and Vic, it was important for them to come up too. They were big to me cause I saw a motherfucker that ain’t to far from where I’m from, and they took off. I mean Chance and Vic are both super duper far now. So that was big for me to watch it, but I’m glad that I’m finally starting to put my foot in the same game type of thing.

AllWon: And I definitely noticed it in your sound on [“toolong.”] that there’s a bit of influence from both sides of the spectrum. The more somber jazzy side of say a Chance [The Rapper], but still that hardness and grit of a Chief Keef.

Woods: I’m from a place where you could be whoever you want to be. You could be both [musically] or you could be one of them. There’s no real division, it’s all Chicago at the end of the day. I fit kind of in the middle, I can go to a party where all they play is Chief Keef and I can go to a party where all they play is Chance – so I’m influenced by both sides.

AllWon: Ok, let’s get into your music – just two songs out, “toolong.” and “Rawest Alive”, correct?

Woods: Yeah.

AllWon: Lets talk “toolong.”, thats really the reason I hit you up. That is one infectious record, man. Tell us about it.

Woods: “toolong.” I wrote that about this girl I was involved with. At the time we were broken up, we hadn’t talked in like two weeks. It was more so a thoughtful record.

But when I made it nobody knew I rapped, like literally when I say nobody, I got two friends who knew I rapped, and one of them was a rapper. Nobody [else] knew – not my parents not my sisters. I made the song and then my engineer fucked with it heavy. It was crazy, I never knew what song I wanted to put out first. I took it seriously; I wanted my first impression to be a good one. So my engineer was like “Yo, this is the one.” So I went with it. Like, if you check my SoundCloud it’s very unprofessional… just cause I didn’t know this was all about to happen.

And then I played it for my sisters, they both ended up crying. I played it for my mom she cried, I played it for my Grandma, she cried.

It just kept spreading. My friends love it, and it just took the fuck off. I had way less expectations for this. I didn’t expect to be talking to a person from Canada right now, I can say that. I just thought it was a cool song to come out with first…

AllWon: That’s a beautiful story, man. And thanks for really touching on the depth of the song, and how it impacted you and those around you…

Now, is there a project on the way? I did some snooping and it seems like trees42morrow may be the title?

Woods: Damn, how’d you find that out? But yeah that’s the title… I dunno how you found that out, that’s a good one.

AllWon: On your SoundCloud you have a playlist named trees42morrow….

Woods: That’s a good hunch.

AllWon: Is “toolong.” on that [trees42morrow]?

Woods: No. I was gonna put it on, but it’s such a big song by itself now. I’ll probably have a lot of new songs for it [trees].

AllWon: That’s a big statement not putting it on – I hope that means you have equal or better records coming…

Woods: I just put “toolong.” out end of May, the ‘tape [is] probably gonna come out in October – It’s projected to come out in October. By then I think “toolong.” will have done whatever it’s intended to do.

AllWon: What about a video?

Woods: Yeah, I’m doing the video with Elevator.

AllWon: Nice. I’ve seen them showing you a lot of love…

Woods: Yeah, they reached out, that was crazy [laughs]… We haven’t started shooting yet, but I got the whole concept and everything done.

AllWon: We’ll definitely keep an eye for that, no doubt. Let’s get into “Rawest Alive”, it seems that it was a track you did for a producers project? What was the vibe with that one?

Woods: Yeah, a producer named Flight, his manager reached out to me after “toolong.” came out. We just connected; they were putting out a beat tape and wanted me to be on it. And then when the song came out it was hotter than we all expected really, so they wanted to put it as the single. That’s how that all came about. It was a really quick process [too] – they sent me the beat, I made the song the day of, and we went to the studio the next day.

AllWon: So in lieu of that title, who do you think is the rawest artist alive right now?

Woods: Kendrick Lamar.

AllWon: Done. Enough said.

Woods: Yeah, that was easy [laughs].

AllWon: Who are some of your other favourite artists right now?

Woods: Cole… but I put Kendrick and Cole in a different category. Those are my favourites ever. But out right now though, I like Future, Vince Staples, Ty Dolla Sign is cool. Chance, Vic of course. Alex Wiley…

AllWon: Wiley is nice with it. Him and Kembe X, I like what they’re doing…

Woods: Yeah, and they’re both from Chicago too which is cool. I like Tink too, it’s a lot of motherfuckers, I could go for days but I’ll just leave it at that for now.

AllWon: It’s good to see you’re in tune with what’s going on. A lot of artists stick with their own music, which is cool, but I think it’s important to take in your peers, see what else is out there, vibe with everyone else…

Woods: Man, my friends always ask why I don’t play my music more, I’m like ‘cause there’s so much good fucking music out. I don’t even play my music when I’m driving…

AllWon: So if you weren’t making music right now what would you be doing?

Woods: I’d be on a basketball team in the NBA.

AllWon: The 5’8 wonder…

Woods: [Laughs] Okay, if I was 6’3 or something I’d be in the NBA. Without rapping period though, I’d probably be entering my 4th year at Columbia College.

AllWon: Is school something you still want to get involved with at all, or is it music full-time?

Woods: I think its music full-time. I took a year off, I went to Columbia for a year, then I took a year off just cause I wasn’t focused enough. I was real focused on music. So, maybe one day… but I can’t see that happening, I’m pretty focused on music.

AllWon: I definitely back that decision.

Woods: [Laughs] Appreciate it. I wish you could tell my mom that…

AllWon: [Laughs]. So, I did some digging on your twitter. You say “People look at me different cause I’m growing up & those [are] the ones I distance myself from”, and then you followed that up with “It’s disrespectful for you to want me to be the same person I was when I was 16″…

Woods: True.

AllWon: In what ways would you say you’re growing up? How has your mindset changed over the years?

Woods: I just don’t let much get to me. And people love drama, I can’t say all people of course, but the people I was talking to are real big on drama. Like, “Oh shit, he said this about you, how do you feel about that?” Like, I’m fucking grown now, that shit doesn’t affect me anymore, words don’t get to me.


And on top of that, really I’m just getting smarter. I read books now and shit. For one, I’ve never really been a party person, but back in the day I would do dumb shit because dumb shit was cool. And I’m not saying I’m 40 [years old] or nothing, I’m just growing into doing other shit. Now I want to make music, I want to read, I want to learn, and I want to help – I don’t want to always be in this state of mind of wanting to do just cool shit, or dumb shit, or buy an outfit for the rawest party that’s coming next. I’m doing different shit now. And all that is cool too, but it’s about balance. And the people I was talking about don’t have balance, they just want to party and drink and smoke, and I do all that too, but it’s just different, you gotta do other things as well.

AllWon: I think you hit the nail on the head talking about the balance that’s needed. I think it takes that moment for an artist to realize they need to ‘grow up’ and change in order to take their career to that next level…

Woods: Right, man. Appreciate it.

AllWon: So what’s next for you? You mentioned trees42morrow coming in October. When do you think we can expect the first single off that?

Woods: Probably… sometime in August, early August. I haven’t been to the studio in like a month, month and a half. Just because I got fired from my job, I didn’t have any funds [laughs]. Soon as “toolong.” came out I got fired like the next day.

AllWon: Oh damn, what happened there?

Woods: They said I was too nonchalant. I’m a very cool person [laughs].

AllWon: Good thing as an artist you can be as nonchalant as you want.

Woods: Right, yeah I just be chilling. And I hate jobs, especially warehouse jobs, being in one big room the whole day…

AllWon: Well if “toolong.” is any indication of what’s to come, there’s gonna be no more warehouse jobs in your future.

Woods: [Laughs] I appreciate that, I’m trying my best. But yeah, I’m going to the studio on Sunday, and I have a lot of songs lined up. And I do have some songs recorded that I could drop, but I dunno, patience is a virtue with me. I don’t just drop every song I got.

AllWon: Last question, why is Jayaire Woods WontoWatch?

Woods: Because I’m honest. There’s not enough honest people, man. That’s all I can say. I’m honest and I’m never going to lie to myself or to you guys, and I’m never going to put out music that I don’t believe in 100%. Even if you don’t like it, just know that it came from a real place.

Follow Jayaire Woods on Twitter @jayairEwoodS

//words and interview by david leigh. follow on twitter @bigleighchew.
No Comments

Post a Comment

Pin It on Pinterest