There are certain artists I hold dear to my heart. Some because their art showed me something new and unique or they had something to say that defined their character. Others because I’ve witnessed their growth and experienced their versatility as an artist. Chester Watson—the Georgia-based rapper, producer, graphic artist, video director, fashion designer in the making, and probably a few more things—is one of those artists.
I, like many Chester Watson fans, discovered him when his hypnotic, DIY-esque video for “Phantom” went viral over eleven years ago. It felt nostalgic yet so refreshing to see a then-15-year-old rapper rap right at you—the video had Chester Watson sitting still and staring right at the camera while he rapped—painting pictures of braggadocious youth and witty one-liners with effortless rhyme schemes over a dusty boom-bap beat. In the following years, Watson began working with artists like Psymun, mejiwahn (FKA Art Vandelay), and Nu Age (his music crew that includes artists like Kent Loon and Kanisono) that would push his evolution as an artist. This brings us to where he is today, over a decade later: an artist with almost 20 projects, including albums, EPs, and instrumental projects, who finds influence in anything and applies it to everything—from music to visual art, fashion, and more.
Watson’s had a busy last year and a half. He released his full-length album, fish don’t climb trees, a mostly self-produced album that mixes meditative soundscapes with confident and introspective raps. He also released the ethereal, hazy collaborative EP with Japanese producer Ill Sugi, Winter Mirage, and the whimsical, smooth—a beautiful contrast to Chester Watson’s usual sound—collaboration with Ontario producer Elaquent, among other artist endeavors and single releases. In between, February’s Winter Mirage and June’s Monisona, I sat with Watson to discuss his influences as an artist, reflections on past releases, the transformation of the music industry, and how he enjoyed the process of taking control of the creative process for his videos for fish don’t climb trees.
I’ve always been impressed by how young you were when you started doing everything. You’ve talked about this a lot, but what was that point when you were young and started getting passionate?
My mom plays a big part in that and why I’m like that. She was always very encouraging honestly, she just always wanted us to try different things and to see what we liked the most. It was one of those things where we tried everything we wanted to do in some way, shape, or form. When I was super young, I was super into Michael Jackson, so I’ve always been into entertainment and entertainers—like Michael Jackson was the shit to me.
At first, I was a singer, I liked shit like Chris Brown and Usher, stuff like that. And then I went into dance. From there, I started burning, and shit like that, I got into skateboarding. I feel like it was kind of a natural progression where the shit that I was interested in led me to other things. Skating led me to hip-hop, and almost directly, it made me start rapping because of the people I was hanging out with and what they were putting me onto.
How has geographically where you’ve been influenced what art you’re into or what passions you’re into whether in the past or now being in East Atlanta?
That’s super important. When I was younger, I didn’t have control over where I was so my surroundings weren’t super important. I started meeting people and skating when I moved to Florida. I was probably like 9 or 10. That’s when I can remember having homies, going to their cribs, having sleepovers, watching WWE, and stuff like that. That’s when I kind of blossomed into me. I was just outside, doing what I wanted to—just skating and listening to music. When you’re skating, you have so much time and you’re probably listening to music in your headphones. So I was discovering hella artists around that time because I would just be skating and listening to music, trying to find the new shit.
I’m curious about the differences between the friends you made in person that you talk and make music with and the friends you’ve made online. How was that contrast for you? How did it feel to open that internet side of the world, versus your in-person reality of people you talk music with probably every day?
It definitely opened my eyes to different music in general, it forced me into a bunch of different worlds at the same time. I wasn’t even trying to make too many friends in my last year of high school because I was already focused on music. And even before then, I already had my friends. That was the feeling when I was here in Georgia. I was talking to my friends online because I had to and in the process, I was talking to new people. I was talking to people who would hit me up through Facebook or email. I didn’t have anything else to do, I was a kid. There were people I finally met maybe in my senior year when I started skating with in Georgia, and I’m still cool with them now like Dev (Slang), and Vash (Noir). Other than that, I didn’t meet too many people here that I still talk to. I think the difference was that Psymun was much older than me. So he knew a lot more than I did about everything—about music, making beats, literally everything. YouTube beats are cool, and trying to make shit with your friends is dope. But if you have somebody who just won 2DopeBoyz beat contests and wants to send you beats, he’s on a completely different level. He was my favorite producer because his shit was just so out there, and then I met Mejiwahn and that opened me up to the whole Minnesota scene. Meeting all these people in these different places introduced me to so many other people because they worked with people in their hometowns. Then, they were introduced to everybody that I was around like Kent (Loon), Kani, and shit like that. It was a real breeding ground for creating the best stuff because we weren’t worried about money, we were just putting shit out. We were all just creating the craziest shit and just posting it because what else was there to do?
How do you look at that era versus today, whether in terms of releasing music or whether it’s from the perspective of a fan of music?
Back then, we were in the early stages of being hyper-connected by the Internet. Right now, you can tweet something and go super viral. Back then, we were in the early stages of that. It was a time right before we hit the point where everybody was super close. You still had to really build with somebody or really get to know somebody. You could still do that now, but now it’s easy to just get a beat pack from somebody, it’s more like “Okay, let’s link online. And then let’s meet in person and cook.” That’s another route that people seek out more often than not now.
Streaming was not a thing like 12 years ago. I remember not knowing how to upload my music onto Apple Music. That doesn’t take away from it now, but it felt like different milestones were accomplished back then. And still, now I feel like a lot of people are like “Damn, bro, I just got my first upload, I just got my first vinyl.” I remember DatPiff, bro, you had to pay like 50 bucks to get people to download your shit for free. I remember having to beg my mom for that. Like, “Mom, can you give me $50, I just want people to download my music for free.” That’s not a thing anymore, it’s very different now. It’s not bad, I just think it’s different.
I hear you. When I was releasing the early EveryDejaVu stuff. I was like, “I want that 2DopeBoyz premiere. I want to track when people are listening on Bandcamp and SoundCloud reposts.” I didn’t care about streaming. That didn’t come until later on. And even when streaming came out, people wouldn’t put it on streaming immediately. It was like “You’re not gonna make any money off that.”
It’s an afterthought. The goal now is to get it to people—to get it to the most people possible. But it was easier to see that. On SoundCloud, people would comment and it felt very community based where we were all kind of like, “Damn, this is the new thing. This is this.” Now there are so many options that it doesn’t feel—it feels connected, but it feels very scattered or dispersed. All these things relate, but they’re nowhere near each other.
Things started changing through SoundCloud when they undid the unlimited reposts. Personally, I feel like that’s when I felt a shift, not the shift, but I felt a shift in a lot of things because it’s like, “Damn, we can only repost it once now.”
Yeah, it’s weird. I know they were trying to stop the reposting like spamming a lot, but—
That’s what we loved about it, bro. It was a lawless land. That’s what makes most of these platforms so amazing, bro. They’re very close to the real world like, bro, I’m going to tell you about the same thing 30 times if I can. That’s the real world, that’s the real conversation. If you’re talking to your friends and trying to really put them on to something, you’re gonna remind them a couple of times. That’s what SoundCloud felt like. It was like, “Bro, this is actually super fire!” And you could do that an unlimited amount of times. You can do it now, but we have algorithms or whatever.
I want to talk fashion with you. I’ve known you collaborating with I Love Ugly for a bit and then I’ve seen you working on clothes. I think the other day you were showcasing some jeans you made. I’m curious about your relationship with fashion, whether it’s creating, or just your own style, or if you have any goals for fashion for yourself. Whether it is a career in it or your art?
I appreciate you showing love to my love for fashion because people don’t necessarily know but you’ve met me in person, so you know, I really like to dress dress. Growing up, we never had bread so we always would go to the Good Will. I remember in there you’re exposed to so much random stuff. You see patterned stuff, stuff from Hawaii somebody got from vacation or something like that. I was introduced to a lot of things through clothing, from a young age. I remember I used to wear cowboy boots and shit like that. I’ve always liked expressing myself through my clothing since I was a jit.
And leading up to I Love Ugly, obviously shout out to them, that’s a blessing. That relationship came about super organically—shout out to Zac. They approached me about making a song for something that they wanted to do. That was kind of the beginning of mine and I Love Ugly’s relationship was through music. From there, I was introduced to them as a brand because I was super young at that point. I may have just graduated. I was probably like 17 when I first got into contact with them. They had a store in LA. That’s when I actually got to really start building the relationship with them because I was out in LA all the time. I remember Max Wonders would come. He pulled up whenever he was in LA and we’d go up to I Love Ugly and just chill out there. I remember they had a bench out front, we’d vibe out because we were still young. Once the LA store closed down, we just kept building, and here we are almost 10 years later. Those are the homies and they definitely acknowledged me when I was younger and saw my vision. They introduced me to a lot of philosophies and I think that they saw that, as a kid, I was super into mind-expanding. We related on an ethos-type level. We both stood for similar things. And that’s why that relationship feels supernatural. V, he’s amazing with words. Honestly, a lot of that stuff, if not all of the wording is from him. In a way, he’s a writer as well. We connect in a lot of ways outside of fashion and because of fashion. I think it was something written in the stars as far as I Love Ugly, I’m definitely appreciative of them and thankful for everything. They’re the homies.
When you were younger or now, do you have any specific inspirations in terms of clothing or just people you look up to? Or are you just zoned into your own creative style?
When I was younger, I always had a vision of how I wanted things to be. Especially when I first started finding my style when I started skating, because before then I wasn’t paying too much attention to brands. I remember the flea market, I was super, super young and I ended up getting a super, super fake pair of Jordans, but they lasted a long ass time. They were a pair of Ones. I think they were red, the Bred Toes. I’d wear them every single day and I started skating in them at one point. That’s when they finally broke. Early on I always wanted to have a style and I always wanted to be fly. Michael Jackson had the high pants and the white socks, that’s something that I do now. I’ll do the highwater pants with the socks for the contrast. Ultimately, stuff like that led me to where I am now, where I know about cuts of stuff. Back then I knew what I wanted it to look like but now I know the mechanics of everything, ever since I got a sewing machine. That ties back into ballet, as well, because that’s where I first learned how to sew. I remember we had to sew our tights and sew the straps onto our ballet shoes. It was just a natural progression from there. I would sew stuff onto my clothes, like patches and shit like that. Or I would fix my clothing. If something ripped, I could just sew it real quick. And then eventually, I got into buying shit from the thrift store and wanted it to be just slightly different, so then I would start hand sewing stuff. Eventually, I just got a machine and started working on clothes, started making pieces. I definitely prefer my style now, though, because I have more money to actually get the stuff that I want and I know more about myself. It’s all more accurate to who I am and what I want to look like.
Can you tell me a little bit more about how you’re able to come up with the six music videos you did for that album now that you do have those resources in place? Tell me about the making of all those videos and the visual aspect of the album. I saw you mentioned Dev and Vash and I saw ill sugi credited, a lot of recurring names.
Thank you for paying attention to those credits. Jeff (Weiss) has been fundamental in organizing everything. When I was a kid, I didn’t know how to allocate my resources. I didn’t know I had resources. Jeff definitely helped me organize everything and, in that, became self-sufficient. That opened the door for me to be more experimental with what I was trying to do going forward, especially visually. I was always telling people “I’m trying to shoot this video, bro. When are you free?” Julia (Updegraff) shot the majority of my videos, like “Trident,” “Creed,” and “Picbas(cassquiato),” but she moved to New York. I just started shooting videos myself and started editing them. I was like, “I gotta take matters into my own hands.” And Jeff was supportive and there for me throughout the process. He helped me organize the train of thought like “To do this, you probably should do this,” and that led me to make more business-minded decisions to further myself. As far as the visuals, that was a trip, especially for fish specifically, because it wasn’t cinematic, but it was cinematic. With the “eyes closed” video where I did the special effects with Tati I was like “Alright, I think I need to do this. I just think this will be dope. How can I make this happen?” So I was on Instagram asking around about special effects, and then I got sent her profile. That was my first special effects prosthesis experience with the ears. It was just a lot of firsts: it was the first time where I was directing shit. It was the first time I experimented and invested in videos, and all of my money went into making the best videos.
Speaking of collaborations, you recently released a song with Toonorth. You’ve been collaborating with him for quite a while right?
I’ve wanted to but this is our first song. I’ve posted a lot of Toonorth stuff because I’ve always loved his beats. Me and Toonorth, we just always showed mad love to each other, and his beats just sound like some shit that I would rap on! I think it was mutual love and the right time. It was like “Bro, we got to work bro. We gotta get one in.” And he sent some beats through. That was the one, it just clicked instantly. I wrote it in a couple of hours, less than a day. Usually, when I write fast, I get in the zone. We chilled on it for a minute, we had it for a while. It kind of felt like SoundCloud again. “You just want to drop this?” That’s the feeling that I’m trying to bring back, even with the ill sugi shit, like let’s just drop it. Call it winter mirage and tie it into a legacy. It’s already on COLORS. So let’s just support each other and create with each other. That’s where both of those things stem from, winter mirage and opal [arrowheads]. Toonorth and I are probably gonna keep on making some shit as time progresses but had to get one in. I got something coming out soon with Joe Nora. I’m probably gonna post a clip with that within the next couple of days. There’s a lot of stuff that I just want to drop. I’ve gotten to a point where I’m still working on albums, but you make so much music, you make more music than what people hear on the albums. I just want to drop it like how I used to—that’s where I’m at now. It’s literally a full-circle conversation, I’m back to “I just want to drop and drop and drop and drop music” because that’s what makes me happy. All the label shit’s cool, the vinyl stuff is amazing. I want to be cemented in time—that’s something I’ve always wanted. But at the end of the day, I want people to hear the message. I want people to hear what I have to say, live with that, and feel my presence while I’m here. The whole posthumous shit is cool, but I want to connect with people while I’m on the planet.
Great final words, but I do have one more question for you. I was reading the I Love Ugly interview, and you mentioned that your goal is to make your art timeless. Throughout this interview and other interviews, you talk about your older music with a ton of reverence. Do you feel like so far you’ve achieved that goal of making art timeless?
Even what I make now, I like and I view it the same. It’s a different form of me, and that’s what I admire about it so much. I can look back on that time and become flooded with memories of what I was doing, where I was in life, and stuff like that. When I look back on it, I want memories of myself—like a journal. I didn’t have a past to look at, I was just living and documenting what was going on in front of me. I’m skating with my homies, I’m getting a crib for the first time, I’m falling in love for the first time, I’m doing all this stuff for the first time. I’m still going places for the first time and having new experiences, going on boats and shit like that. It’s just different stuff. I think that sense of adventure is always within me, and that’s what always makes it exciting to look back on because I try to put so much of the spirit of how I live and what I’ve done/what I do into the words, and even the beats. I’ll probably always look back on it with a smile or a deep thought and just appreciate it because I make so much music, so for me to compile something and put it out, I definitely went through a lot of stages of listening to that and doing stuff while listening to that music. For me, it’s more so what the experiences hold in these songs and that’s why I speak on them with such love and such high regard because they represent a point in time in my life, and I think it can be that way for listeners too, they can have a time where that was the soundtrack, bro. Music does such a good job of capturing that. I love that.
