WebsterX is unafraid to reach back into his bleakest memories to offer “a peek at what the dark feels like.” The Milwaukee rapper describes 2014 as the year he felt the furthest from his best self, the year he was often immobilized by sudden depression. Raised in a family of Ethiopian immigrants, the value of hard work was often stressed, but the importance of mental health mostly ignored. As a result, he often sleepwalked through weeks on end, feeling detached from his own life.

He began working through his pain in the wake of 2015’s “Doomsday.” It bled into the completion of his debut album, Daymares. Chronicling Webster’s journey towards psychic health, it opens with a dreary atmospheric beat and the sounds of screams. It closes with a grandiose soundscape bathed in sunlight. Symbolizing his time spent “hiding from the world,” Webster created the “Lost Identity Mask” pictured on the cover. We hear his anxieties and can see the aftermath on the album art: a scar on his head and a portion of the Lost Identity Mask torn off his face.

A fledgling and unexpected hotbed for art, Milwaukee made national news in 2016 because of riots and a hyper conservative sheriff. But Webster wants listeners to know that the city is more than the sum of its political tensions. Artists around Milwaukee support each other and host events to combat violence in the community. A member of the New Age Narcissism collective, his crew reflects the diverse talent pool spanning the city, ranging soul-pop to hip-hop, to genre-bending instrumentalists. NAN’s own Q the Sun shouldered much of the production on WebsterX’s debut.

While Milwaukee may not have a set model for rising acts to follow, the recent Closed Sessions signee is helping to lay the groundwork by example. Stylistically, he fits in with the likes of Allan Kingdom, Kweku Collins, and Isaiah Rashad. His music strikes the “balance between being hype and being chill,” meshing together the emotions of dusk and dawn. Now regarded as a mainstay in Milwaukee, WebsterX is facing the hardest step: breaking nationally.

I spoke with WebsterX on the phone about Milwaukee, his artist collective, and 2014. —Donna-Claire

Let’s talk Milwaukee. Milwaukee has produced many rappers, but not many that break nationally. Why do you think that is?

WebsterX: Milwaukee has that sea market type of vibe. There’s no real legacy as far as hip-hop goes, or any history to follow here. So a lot of people have to make up their own rules here, and that’s the same for other cities in the Midwest. Milwaukee is really the ground-zero for hip-hop in a sense. Nothing has gone crazy nationally. I mean, we had this rapper named Coo Coo Cal, who at one point had buzz going nationally, but that was just off of one song in 2002. There has to be a whole bunch of ground covered for us to have any type of relevancy nationally, and that’s still being worked on. At the end of the day there’s a lot of different people here trying to be pieces to the puzzle and make things happen.

What obstacles did you have trying to navigate the city’s music scene as a rising hip-hop artist?

WebsterX: Personally, there’s not as many resources here as there are in most places. For me, I had to figure it out all myself. I really came from a DIY standpoint. I was blessed enough with my situation to naturally find the right people to work with, to make my music and have a team behind it. Honestly, those were just my friends.

So obstacles I faced: trying to find shows. When I really started going at this professionally as WebsterX, that was in 2013, I landed a show by that next June. It was super awesome; I was reached out to randomly. I performed at this place called Landmark Lanes, which was this bowling alley/barn type of place. It had one random room in the basement and there were a lot of people. I just brought a lot of energy to the set, and I brought myself. I was just myself and that snowballed. All of a sudden I started picking up steam here in Milwaukee, playing show after show after show. I was really doing something that was exciting and had some creativity behind it.

See it’s not really many obstacles, it’s just one obstacle as a whole and that is you don’t have many resources here. So artists have to try and make it out themselves and use the people around them. Then over time, we have this radio station here called 88Nine Radio Milwaukee, and they provide a lot of support for local musicians. But you still have to make a name for yourself to get their support.

With that lack of resources, how vibrant is the local hip-hop scene? What about other cities of the same size, like Minneapolis?

WebsterX: With other cities, people have some sort of model to follow. Myself, I’m in a collective called New Age Narcissism (NAN), which is comprised of a bunch of different artists from soul-pop to hip-hop to full on…you know it’s hard to put it all in a box. There are singers in the group and there are instrumentalists. We just try to do as much as we can to excite the scene as a whole. Now, what’s happened since 2013, there was a movement of musicians that were getting excited and moving forward in ways that I thought were dope: tastefully providing a package that was online. This was also happening outside of the hip-hop scene: indie, metal, a whole bunch of people. The only thing is, people sometimes get caught up in that and feel like some kind of local celebrity. You can’t ever get caught up in that, because there’s always more work to do.

Milwaukee does have a great art scene, that’s outside of music as well. The only thing is, Milwaukee is a very segregated city. So people always try to demonstrate that that’s a problem we face. The Northside of Milwaukee is predominantly black; the Southside is predominantly Latino; the Eastside is all the University types; the Westside is more so an extension of the Northside. So you see, there aren’t many bridges. So we we have to kind of create these bridges for ourselves. When I started, this was the mission: I wanted to make sure I could make a stamp. Not just by myself, because I will never be able to put on my for my city alone, but if I can get the fire started and do anything I can to get people excited then my goal is complete. I’m at that threshold now, with that crossover of national attention. That’s the hardest part.

Do you think an art collective is the key to working the music scene in the Midwest and creating those bridges?

WebsterX: I would say it helps, but I’m not gonna say that it’s necessary. It just really depends on you and what you bring to the table. I’m the type of person that is extroverted. So if you’re the type of person that can ignite some sort of fuel, then things can happen and bridges can be made by yourself.

The reason the collective that I’m in really works is because we are all so diverse, especially all of our works. My buddy Lex Allen wears a bun and is a gay black male, but at the same time nobody really notices because he’s just him. There’s Siren, who is a female white woman. There’s Chris G, who is a dancer and wears a bowtie every single day of his life with a full suit because that’s him. My buddy Q plays keys for me and he’s Indian. Not even to go too much into race, but this is really what the group is like. Lorde Fredd33 is probably the closest to me in sound because he also makes hip hop, but he would kill me if I said that because you can’t really box it in. We are a type of group you have to see for yourself to truly understand. The collective that we bring totally helps, but you don’t ever need four or five people around you to make everything happen.

Your friends sound sick.

WebsterX: Yeah my friends are tight as fuck! I’m very fortunate and happy as hell to be working with them. We all found each other naturally. If I get a chance to sneak them in, I do. Over the years we just found each other at different times, in different places, and we realized we wanted to put a name under all the shit we do together. We meet up every week and we built up this family relationship together. That really fuels what we do, and I think that’s why we are able to make such a stamp in Milwaukee. I didn’t really find them, or join the group until 2015, but I met everybody way earlier.

Milwaukee had riots break out last year after Sylville Smith was murdered by police. Where were you when the demonstrations began?

WebsterX: Well, I was actually at the barber shop when that all happened. One of the dudes at the barber shop was on the phone and he had heard about one of his friends being killed. He was just talking underneath his breath and seemed out of whack. It turned out it was actually Sylville. That situation as a whole was really bad, it was right around where I grew up, but honestly it’s kind of weird. See, that happened and then things moved forward. People just forgot about it, which is not the greatest thing. You always want great art to come from these types of situations.

How did the local scene and community react to the riots?

WebsterX: There wasn’t much of a reaction in a sense. Some people did react, and it was interesting. At the same time we were all at this event called Strange Fruit. This guy Jay who plays sax, he’s an extension of the NAN family, and his event is a three day music festival that was held to combat all of the killings that happened this past summer. That night is when the riots started happening and it was kind of ironic, but all my homies were just trying to figure out how we can go over there to try and help. At the same time, when a situation like that happens you can only help so much. You have to be aware and attentive at all times. Otherwise, I’m just going to continue doing what I’m doing with my mission of making music and art, and inspiring people. Simple as that.

Let’s jump into the new music. Going from Desperate Youth to Daymares, it sounds like you’ve really graduated as an artist. What was the initial spark for this evolution?

WebsterX: The spark was a lot of transitions. Between Desperate Youth and Daymares, my journey as a musician changed a lot. I was doing more shows outside of Milwaukee. At one point, I pretty much stopped doing Milwaukee shows because you don’t want to oversaturate. So I was going out and doing shows elsewhere, like New York and SXSW. I was spreading my wings as much as I could.

The story behind getting to Daymares starts after I released the mixtape Desperate Youth. It did exponentially well—especially in Milwaukee—to the point where I was like, “whoa!” I had all this extra attention, and I wanted it, but wasn’t sure how to navigate it moving forward. With that, I spiraled into this really dark place. It was really the first time I had that kind of depression and anxiety. Especially in my household, see both my parents are Ethiopian so we never really talked about that kind of thing growing up. It was more so, my parents never complained too much. They came here. They wanted to get stuff done, and they influenced me in that way.

So there were really big growing pains pretty much all of 2014. I didn’t really come out of it until I released this song called “Doomsday” and I made a really cool video for it with my buddies Cody and Damien. The video got a whole bunch of national attention, from there I was like, “Holy shit, it’s time to put yourself in high gear.” From there, I had a lot of collaborations. I linked up with a lot of people that I wanted to link up with. It was a dream. I made a song called “Kinfolk” with Allan Kingdom. It was all me manifesting what I wanted to make happen.

The time I actually started the project Daymares was mid-2015. I started with my homie Q, who executive produced the entire project and plays keys for me live. He’s a super awesome dude in general and he’s also in NAN. We made a few songs here and there, and then we decided to chill on the album for a bit. Then we released this EP called KidX, which was kind of a transition bridge from Desperate Youth to Daymares. KidX was inspired by Radiohead and it was a very transitional project: three tracks, super simple to digest. From there, I went on my first headlining tour ever in the Midwest; it was eleven days. The tour was super successful, and at the last show we sold out my hometown at a 400 cap. During the tour I was telling my manager Nick, “Dude, I gotta finish this album. I gotta. As soon as tour is over, this is the next step.”

I’m always thinking about my entire career just in a timeline. I’m super stoked, because I just get off on making plans. So after the Lost Ones Tour, which happened in May 2016, I got back home and it was the summer. Then I played Webster Hall in New York with Black Milk in June. After that happened, I really got cracking on the album in the summer, fall, and winter of 2016. I was really in this mode of clarity.

The funny thing about Daymares is that it’s a concept album about a dark time in someone’s life. As you go through the album, you realize that it’s a life album in a sense. Especially if you’re from Milwaukee, you can connect to a lot of the lyrics because I’m referencing specific places: University of Wisconsin Milwaukee where I went, and other random shit. So I dub it a life album. We wrapped it up in February of this year, and from there it really documented my artistic journey from 2013 to 2017, which was a crazy rollercoaster.

Was it the tour, or was there any one track that once you finished writing or recording it, you knew Daymares was going to evolve out if it?

WebsterX: During the tour and towards the end of the tour I realized I really needed to get the album done when I was finished, because the tour was going so well. The tour made it clear to me that the album was the next step. There wasn’t really one specific moment, I was just thinking about it. When I’m at my best self and I’m in that heightened energy, everything becomes clear and I get excited about every single plan. When those times happen, I definitely take advantage of them.

Even before the tour I started the project, but I was just taking my time with it. After tour I wanted to get it out at the end of 2016, then we signed the distribution contract with Closed Sessions and they helped me figure out a good timeline to release. That’s when we figured out March 2017, so I had even more time to work on it.

I was also working with a lot of great producers, which made the entire job easy. I’m the type of musician that can connect with a song and write very quickly to it. Usually I can write a full two verses, chorus, and a bridge in the matter of an hour or two hours. It depends on the vibe in the studio, and I like to make my music in person.

Take me to the recording days of Daymares.

WebsterX: The project really started off in mid-2015, and I wanted this thing to be my debut album. Actually, before Daymares, I had already made a fourteen to fifteen track project that I totally scrapped because I thought it was too dreary. I was writing it from that anxiety-ridden standpoint, but I was writing so much music it didn’t matter, because I knew I could stand up and get right back at it.

The project started off with Q the Sun, and from there it evolved into me working with different producers: oddCouple who’s on Closed Sessions, BoatHouse who’s on Closed Sessions, my buddy Simen Sez who lives in New York. Throughout the entire process of making Daymares I just had to focus, refocus, and focus again on the concepts I was talking about. That’s the thing when you’re making a conceptual album, sometimes you have to go back to the places you were in or stick to a certain topic so it can be more cohesive. I was just making sure I was grooming this project with a fine comb. Q helped with that because he was taking notes. I also kept this orange notebook because I watched this Kurt Cobain documentary called Montage of Heck and I thought it was super dope that he kept a journal. So I thought maybe a journal would really help me organize my thoughts and it did. I was logging stuff in this journal and also writing down the number of songs that I had and how many I had to cut.

The reason why this project is really called an album is because the approach I had with it was a very album oriented process, you know? There were cuts made, there were really professional studios. I was working with some of the best engineers in the goddamn region. It all came together and I tried to make the music that felt most real to me. I was trying to make music that would be dope in a live show setting, because that’s one of the best settings you can see me in.

In terms of sound, Daymares really lives up to its name with somber beats accented with synths that sound like daybreak. Did the name come before the sound, or did you hear a few beats and think up the name?

WebsterX: The name Daymares came from my buddy Kenny Hoopla who used to shoot live photos for me at shows. He had posted a photo once and the caption was “Daymares,” and I thought that embodied everything I was going through at the time, so I just kept the title. I had it for two years. It’s also a word I didn’t know existed, but it was exactly what I was going through. You know, anxiety and all this shit just happening throughout the day. Not being able to get out of bed and do the shit you need to do, and you know, not feeling like yourself is one of the worst feelings ever. So I just used that as artistic fuel, and that’s why the Daymares name never changed at all. It’s so tight to just see it on Apple Music and see it in interviews. It’s really inspiring to just have your thoughts come to fruition.

The production across this record is dreamy and somber. What was the overall mood you were looking to convey with this project?

WebsterX: I was trying to balance dark and light, and it was really as simple as that. Having the album start off kind of dark and then let it break into glimpses of sunlight here and there, like on the track “Lost Ones.” I would say the first two tracks are super dark, and then “Lost Ones” and “Underground” are a little lighter. Then you kind of go back into it on “Soul Shatter,” then going into the interlude, which was a voice memo. Breaking into “Skin,” which is a song fully submerged in sunlight. All of that embodied the rollercoaster of emotions I was going through, and that kind of happened naturally. That’s when you know you’re making the best product, when it kind of makes itself in a way. I knew I had some gold in my hands making that tracklist, so we made sure the way the songs were ordered was incredibly important to us.

So speaking of balance, how do you get yourself back to center as an artist?

WebsterX: Taking a lot of alone time and watching movies. I watch a lot of interviews from random artists here and there. Taking my time away from people, I’ve realized, has been a really good thing. It keeps me balanced. Next week I’m gonna be in California all week, and after that you can catch me at the crib for a full day at least. Taking that alone time and being able to reflect is really awesome. I love being around people, and I always have my entire life, but as things have gotten more serious and busier, things can be overwhelming. So it’s really important to go back to center and take some time to reflect on what just happened. I like to use all that stuff as fuel, you know, experiences are what drive my music. I haven’t started writing any music after this album, and that’s purposeful because I need new life experiences to make this next project. What centers me is being able to study myself.

On “Tick Tock” you talk about the line between pain being inspiring and bringing you down. How do you strike a balance between using your pain in your art and getting lost in it?

WebsterX: The way that line is dictated is during that anxious-ridden period, I couldn’t see light for a minute. So I had to see light through my girlfriend and light through my sister, who was giving me advice here and there. When I came out of that time period, I realized that it was really all a test. That line is really hard to be on either side of, but I’m super grateful that I was able to recognize that the dark period was actually really necessary for me. If I didn’t go through that, I think I might have been more arrogant and not realize that people have those feelings. I would’ve been ignorant to depression and anxiety. It’s kind of funny to see the trend online with black mental health, because that’s the shit that people are really going through. There’s all types of articles going super deep. It’s just perfect timing with me talking about all this shit and using it as fuel.

As a fan, I tend to gravitate to artists that are genuine in discussing their struggles.

WebsterX: Yeah, we all have that intuition about how we hear things. It’s really dope to see people talking about this shit, but for me personally I know I won’t be talking about this forever. This is just one album, and I always tell people this next album could be about cotton candy and Lamborghinis. It all depends on my life experiences and where I’m going to move forward. Spitting your honest truth is the dopest shit to me.

I love the way you deliver that one line off “Future Projections:” “WebsterX, goddamn he’s next.” You sound like you’re having so much fun with it, was that the general studio vibe during recording?

WebsterX: So “Future Projections” is actually a hilarious song. It was a song we almost cut last minute, just because it has that industry hip-hop sound to it, but we did that on purpose. Me and Q made that track together. So the intro has that introspective Q the Sun sound, but when the beat drops it sounds like “10 Bands” by Drake. That’s the whole point. I wanted to make something that sounded industry type, still do it in my own type of way, and kill it. I wanted to showcase my versatility. And that “WebsterX, goddamn he’s next” bar, you know you hear all these rappers in these songs flexing super hard. I decided to do the same thing, but it’s not usually in my nature. It doesn’t mean that I don’t want to do it, but in music I don’t really gravitate to that, “I do this, I do that, I got this watch” blah blah blah. When I wrote that line, I thought it was gonna be so funny to yell in the studio. It’s supposed to be a little sarcastic.

Do you like to set a certain atmosphere in the studio before you start working?

WebsterX: I work out of three different atmospheres. It’s either I get sent a beat, or I make something with a producer in person in the studio or at their house, but then I have to finish it at my house. Or, I just make an entire song in a studio with a producer like BoatHouse; that song “Kinfolk” was completely made in his studio at like 2AM. There are other times where I go to a producer’s house and kick it. That’s what I do with Q, because he’s got all the equipment so I just go over there. I make the music in person with him and I also like to dictate the type of energy that I’m gonna have on a song. I don’t like tracks to always be emailed, because at that point it doesn’t feel like we made it together. The best music is when you make it together.

On “Lost Ones” and “Underground” you allude to 2014 as being one of the worst times in your life, just straight up. What happened?

WebsterX: In 2014 I wasn’t me, and I couldn’t feel like myself. Growing up I was a shy kid, I didn’t talk too much, but I never really thought about anxiety. There were no points where I couldn’t get out of bed, it was either I was tired or didn’t want to go to school. So the period of the depressive state I was in was late-2013 and all of 2014. I’m not gonna say that 365, every single day I was depressed, but I was in a state where I wasn’t my best self. After “Doomsday” came out, for some reason I really just popped out of it. That song’s chorus was speaking a lot about life at the moment. I always see people talk about life as if everything is crumbling, but that’s probably not gonna happen. You’re probably gonna wake up tomorrow and have the same exact life. That chorus was also speaking a lot about myself. We have so much time left, and we all get freaked out about time as a whole. That’s where “Tick Tock” comes into play, too. That song is speaking about time and our relationship with time. So I just used all of 2014 as a canvas and used it as fuel for the album. If something happens and I find it really powerful in my life, I’m going to use it.

Also, I’m sure you’ve noticed that mask on my cover art and my singles, that mask is called the Lost Identity Mask. It’s a mask I made as a symbol of me hiding from the world. I have this mask too in a sense of going through life and I never really admitted to anyone that I was feeling like this. If I can’t spread any good energy outside of my house, I’m just gonna stay inside my house, which is really not what you’re supposed to do. You’re supposed to just go about your day normally, so I would try and do that and it didn’t feel real. So I thought about that as walking through life with this mask on. At the same time, maybe if we all had this mask on, we would be more comfortable. There were times where I was thinking about duplicating the mask and having some at my shows, having people wear them. That still might happen.

Overall, it was a growing pain period. I dropped out of school, and I was worried about my parents and how they would feel about this. Over time I was winning some local music awards here and starting to get some national acclaim, and them seeing me in the newspaper, that was more validation for them. Some of my awards are more so my Bachelor’s, because now that they see what I’m doing is really paying off. Obviously I’m in a way happier headspace now, and it’s weird to relive that time period through interviews, because I still learn new stuff from it.

Was it difficult to write for Daymares since you had to reach back into those darker memories?

WebsterX: Hell yeah. Sometimes I would get randomly stuck, because I wouldn’t really remember what I was feeling. It’s hard for me to stay on topics sometimes, because I’m a really free-flow thinker. At the same time, when you’re writing an album you have to consider how it’s gonna come off to the listener. So if you’re talking about being in this depressive state and then you’re talking about riding around in the hills on the next line, it’s gonna be totally different, the listener won’t be able to follow, and it won’t be a great song. So like I said earlier, it was that focus and refocus on topics, that’s what I had to do.

Some songs wrote themselves, but some songs wouldn’t. There were times where I would write a first verse then have to come back later for the second verse. I just had to accept that, and push myself through the times of making it. I just had a great time making an album. It’s also dope, because this is my first album and I knew what it could do for me and what opportunities it could bring, which is coming to light right now. I just kept trekking, it’s all I could do.

Does the album feel like a cathartic experience for you?

WebsterX: Oh yeah, 1,000%. I was telling my manager when I release this, that’ll be closing the book on that chapter of my life.

Are we getting a full Daymares tour? And more importantly, will you be making any hats? I love hats.

WebsterX: As far as a Daymares tour, we’re moving into it very slowly. We’re doing four Daymares shows off-top from the project. I’m playing in Santa Ana and LA next week with Injury Reserve. Then I’m headlining Baby’s All Right on May 4th. I’m headlining Turner Hall Ballroom on May 26th, which is a 1,000 cap venue in Milwaukee. After that, I would assume a tour would come about. I most definitely want to go on a nationwide tour for the project, that would be dope. Being a support act for a bigger act would be dope as well. Merch will also be coming soon, so you’ll have to be on lookout for that on the website. Hats—I don’t know about hats, but now you got me thinking.

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