The first time I met WebsterX was in his hometown of Milwaukee in the fall of 2015. I remember hesitantly walking up the steps of a friend of a friend’s house, knocking on the door and being greeted by an extremely tall person with short locs and a wide smile, welcoming even though he didn’t know me. But I knew him immediately. I had just written a Milwaukee rap scene report for Noisey and was already well-versed in the city’s scene.
Recently, Web reminded me that that moment—in the fall of 2015—was an important juncture for his city. It was when Milwaukee’s rap scene turned the corner and began garnering national attention, with him and his eight-pronged collective New Age Narcissism (NAN) leading the charge.
But for WebsterX, it’s been a slow build. While he released his debut mixtape Desperate Youth in 2013, it was his 2014 single “Doomsday” and its subsequent video that gave him his breakthrough. He dropped his second offering in late 2015, a collaborative EP with NAN producer Q the Sun, called KidX. Now, after announcing a distribution deal with Chicago indie darling Closed Sessions in fall 2016 and subsequently releasing his 15-track debut album Daymares this past March, Web is inching closer to the top of his game.
Though WebsterX’s dad was a famous musician in Ethiopia—he went by the moniker Abdi Guitar and was in a group called the Roha Band—a career in music didn’t hit for Web until he was in college. He developed an interest in poetry during high school, benefitting from the education integration program Chapter 220, which promoted racial and cultural unification by busing city kids to schools in the suburbs. “It just opened up my world to different things than the normal northside kid in Milwaukee would have at their disposal, which I’m always super grateful for,” he says to me over the phone from Milwaukee.
He started going by WebsterX during his freshman year of college at the University of Wisconsin-Milwaukee (UWM). “At that time, like I thought I was super cold with the words, and I was like, ‘Ah, Webster Dictionary! That’s the perfect correlation. I’ll call myself Webster.’ I threw the ‘X’ in as like a lost identity—me going into music feeling like I don’t want… titles, no real attachment.”
Since his father was an acclaimed musician, Web’s family was all too familiar with that lifestyle and weren’t pleased when Web decided to drop out of school and pursue a career in rap. “It’s just like typical immigrant parents, the pressure they put on you to get a good job. They just want the best for you because they risked so much to come here.” It wasn’t until Web's name started to appear in local newspapers and on national sites like Entertainment Weekly—and winning three 88Nine Radio Milwaukee Music Awards in 2015—that they recognized his success.
“From how everything started, I realized that if I wanted to make a big impact elsewhere, I had to start in my own city first,” he says.
Indeed, Milwaukee has always been the crux of his music. When he was still in college, Web lived with his friend and videographer Damien Klaven (who shot the “Doomsday” visual), where they threw massive parties, packing at least 200 kids into their house. Together, they cultivated a gigantic social network, so by the time Desperate Youth came around, it was well received.
Between 2013 and 2015, he played around 200 shows just in Milwaukee; and during that time, in late 2014, NAN also hit the ground running, a group whose mission is to “embody self-expression through music, visual art, and performance.” In Cream City, the cream rises to the top: Together, Web and NAN carved their own niche and became a force, known in Milwaukee for their dynamic live shows and their knack for synchronized dances.
“When we sold out The Miramar, which is a 400 cap venue, I was like, ‘Alright, I think my stamp is here in Milwaukee. How can I help the city now?’ Just tryna do my own part because my parents always taught me to treat the next person like your neighbor. I felt momentum building in Milwaukee. It wasn’t even just me: It was IshDARR, there was a lot of random artists; 2015 was a huge year for Milwaukee hip-hop.”
WebsterX bolstered Milwaukee’s growth that same year, by attacking it from a DIY angle and building Freespace, a monthly event where he and his co-founders—Vince Gaa, a Milwaukee Public School teacher; Janice Vogt, a graphic designer; and Kane, a local rapper and their first featured musician—would bring a guest youth artist mainly from the city’s north and west sides (where a majority of the city’s rappers come from) to Milwaukee’s eastside (which is near downtown and where UWM is located). “We needed to bring these people without a voice to this space where they can have a voice,” WebsterX says.
Web has applied that same DIY mentality to everything he’s done so far, but with the rollout of Daymares, he did things a bit differently, handing the reins over to Closed Sessions for the record’s release. Still, the move was organic: The label and Web have been longtime collaborators; Daymares’ production credits include beats from CS producers Boathouse and oddCouple. Among the tape’s other producers are Milwaukee rapper/producer Mic Kellogg, as well as Q the Sun, who produced almost half of Daymares, and executive produced the entire project.
Each WebsterX project embodies an experience he’s endured; Daymares, in particular, is an album based off his growing pains, rooted in the depressive, anxious ridden state that he went through in late 2013 and early 2014. “It stems from me like having to drop out of school and tell my parents that, releasing the Desperate Youth mixtape, it doing really well in Milwaukee and me realizing like, ‘Alright, damn, I was not expecting all that reception, what do I follow it up with?’
“It was my first experience with [depression]. I never really knew what depression necessarily was or anxiety ‘cause that was never really talked about in my household… it’s really a taboo on the northside where I lived.”
Daymares documents the entirety of his career, from when it started in 2013 to present day. “I didn’t start writing the album until after that period; it brought me out of like that weird spot, “he says. “Some sort of natural progression was happening that was starting to open my eyes up more—it was a lot of self-analysis. So for Daymares, I was starting to write from a positive standpoint, [and it] went from being a conceptual album about like just this dark period I went through, to turning into a life album as well.”
That sort of self-reflection Web experienced is evident throughout Daymares: Songs like “Underground” and “Future Projections” question his come-up and fame, while “Until” addresses his depression and anxiety, and “Lost Ones” pulls the throughline from his earlier rap days.
Daymares, too, is a sonically cohesive vehicle, intuiting the same haunting and ethereal mood throughout. Whether it’s synth-heavy songs like “Lost Ones” or bass-driven tracks like “Intuition,” the record shuffles through the motions of a young man feeling adrift and finally finding his place.
For his 2016 Lost Ones Tour, WebsterX created a mask, which he nicknamed the Lost Identity. Initially, the mask allowed him to hide from any self-doubts, but what it also helped him realize is that we have to celebrate our differences, whether they’re failures or wins. It's that realization that he fully grasps on Daymares.