In his 2017 debut album Daymares, WebsterX explores the complexity of emotions and offers sincere reflections about his personal sentiments. Incorporating introspective subject matter into refined and precise production exemplifies the masterful work on the album as well as the artist’s previous project, Desperate Youth. The enticing tempos that sway from the melodic “Underground” to the hard-hitting “Heaven’s Gates” constantly keep the listener enthralled, rather than merely falling victim to the problem that many of his contemporaries face of utilizing the same generic FL studios bass-heavy beat. WebsterX’s thought-provoking lyricism derives from a genuinely honest perspective, so it resonates vividly with his listeners. He is a symbol of originality in the rap world, as his diverse take on production and poignant content converge to form utter uniqueness.

“Daymares is titled as such for two reasons, one being the visual reason. I like how the word looks and sounds. My friend Kenny captioned a photo ‘Daymares’ and posted it. I saw the word and immediately gravitated towards it and knew right then and there it’d be the title of my debut project,” he explained. “The second reason being the meaning behind it. Daymares are nightmares that are happening during the day, and the album touches on the first and only real big dark period I went through in my life, in years 2014-2015, in that 2013-2017 period of my career thus far. I couldn’t function much during the day because I was plagued by my first experience with depression, anxiety, self-doubt and simple growing pains, worrying about dropping out of school to pursue music and having to tell my parents that, because music was going crazy for me locally. Worrying about the large local reception of my debut mixtape Desperate Youth and how to follow up, all that.”

The 2014 single “Doomsday” has garnered north of one million streams on Spotify and induced the buzz that established WebsterX as a significant presence in the minds of many music fans and critics. The artist’s delivery on the track is innovative and captivating. Ominously enchanting cadences float above the track’s instrumentation and blend with the artist’s light falsetto, confirming the track as an enthralling hit, despite its dark lyricism.

WebsterX explained, “‘Doomsday’ was written during that dark period of mine, originally intended to be the first single for the first version of Daymares I made and eventually scrapped; it blew up pretty much from the blogs. The video that I made with my videographers Damien Blue and Cody LaPlant also set the song ablaze; they do all my videos and absolutely go crazy. The song sits over a million now on Spotify and is the reason for kickstarting my career into national attention.”

The creative process for WebsterX emanates from writing in a peaceful state of mind while concurrently reflecting on any hardship he previously encountered. WebsterX said, “ I can only write from a happy, driven and calm perspective. So during the depressed and anxious-ridden points, I never wrote. Once I overcame that period I reflected and wrote about it all from a clearer perspective, which made Daymares. In the last question I mentioned I scrapped a first version of the project; that would be because I tried writing it from a dark mindset, and to me it was just too dark and slow. The version of Daymares that is out today is more of a life album because lyrically it’s not all about that dark period in time.” 

Courtesy of WebsterX

The result of writing in this clear mindset, rather than one submerged in calamity, ultimately made a project that depicts a narrative of a young man experiencing the trials and tribulations of adult life, specifically addressing the tangible effects of sadness on one’s mental state.

Both of WebsterX’s parents are Ethiopian immigrants, making him a first-generation American, but he is not the first in his family to pursue a career in music. About how his roots in Ethiopian culture impacted his creativity, he said, “Ethiopia is a one-of-a-kind place in Africa and around the world. It’s looked at as a mecca to some Rastafarians, the cradle and start of humanity to the science world and a place full of beautiful people, music and culture to me. My parents are both Ethiopian; my father was a professional club soccer player and famous musician in the country and my mother’s side of the family is a coffee business of royalty. My father without knowing it instilled kindness, wiseness, love and creativity into me. My mother brought toughness, empathy for people and directness to me. With that I feel I balance both very well, and my older sister put me onto all the cool stuff I know today at a very early age.”

Kid Cudi reflected on melancholic realities with progressive instrumentation and cathartic flow that pushed musical boundaries, thus making him one of the top influential rappers for younger generations. The Milwaukee rapper WebsterX cited Kid Cudi as one of his major influences.

Kid Cudi emerged at a time when people who were born between 1990-1997 were experiencing middle school and high school,” he said. “For a rapper to come out with this lonely stoner, cosmic tone to his music and a melodic delivery along with good-feel raps, he simply had the relatable factor on his side.” He continued, “Being associated with Kanye was also crucial because Kanye was running our generation’s iPods at the time and pretty much still does. Cudi’s music was also very chorus-driven; [which was] a big and addictive reason why I think they resonated with a lot of people, including me. From his style to the music, he felt like one of us even though he was 24 at the time that this was all happening for him.” Similarly, WebsterX has crafted his own unconventional style, yet he remains an impactful voice that is simultaneously emphatic and relatable.

Recently, WebsterX joined his friends from Injury Reserve to perform a couple of live shows around the SoCal area. “IR are the super homies,” he said. “Those dudes [and] their team are incredibly talented and everyone who is fortunate enough to realize that, realizes it. They didn’t teach me anything necessarily, but what was happening was more of a realization of who they are as people and why their music sounds the way it does. Both camps got closer and still retain that relationship to this day. To me, they’re one of the most refreshing, straightforward, exciting groups out today. Both of our shows in Cali were major, especially the LA show, sheesh.”

Injury Reserve and WebsterX share a dynamic of creating spaces to craft seamlessly gravitative rap songs that are entirely divergent from their contemporaries. They are the embodiments of unapologetically challenging what rap should sound like, as they offer sonically experimental tracks with progressive lyrics that open up thoughtful conversation about themes that are relatively taboo in the rap realm, such as depression and insecurity.

A rapper and his hometown go hand-in-hand like a symbiotic pair; take Chance the Rapper and Chicago, Jay Z and New York, Kendrick Lamar and Compton for example. WebsterX hails from the city of Milwaukee, Wisconsin, a city that is stereotypically known more for its cheese than for being a forerunner in producing rap artists. WebsterX explained his deeply rooted origins in the city of Milwaukee and the distinct passion he holds for the location, citing a plethora of exemplary and incredible artists to come out of the Milwaukee community.

“Milwaukee is a full-blown city, fifth largest in the midwest,” he said. “Briefly, Milwaukee can be described by its four locations: North, West, East and Southside. Northside is predominantly black. Southside is predominately Latino. Eastside is the coming-of-age college town, yuppy central and affordable hip neighborhood. Riverwest is where all the music is popping mostly out of the city across all genres and downtown Milwaukee is on the Eastside mostly. The Westside is sort of jokingly no man’s land, a mixture of north and west. If you were coming from out of town, mostly everyone would recommend the Eastside of Milwaukee to you for artistic spaces, live music, sporting events, pretty much everything entertainment wise. The Eastside brews and takes in the majority of the indie pop/rock, folk, metal, hip hop, rap, etc. acts in the city. We have our fair share of bigger acts coming out of Milwaukee as a whole such as IshDARR (Northside), myself (Eastside), Vinyl Theatre, who is on tour with Twenty One Pilots right now (Eastside), Field Report, a slight extension of Bon Iver (Eastside) [and] Grace Weber (Eastside) who was on Chance’s Coloring Book, as well as the very talented acts and personal favorites of mine who are really on the come up: Zed Kenzo, Taj Raiden, Platinum Boys, Soul Low, Milo, Foreign Goods, Boodah DARR, Kane and my collective New Age Narcissism consisting of Siren, Lex Allen, Lorde Freddee and Q the Sun. If you ask me about Milwaukee I’m gonna need a few paragraphs; I know too much.” 

Courtesy of WebsterX

We asked WebsterX about the difficulties that accompany a music career founded in such a city as Milwaukee. “The only thing that’s difficult is there are no real resources here,” he said. “You really gotta do it yourself or with friends. There’s lack of management, no booking agents, not many all-age venues and more. However, due to the recent successes of a lot of emerging acts, Milwaukee as a whole, musically, is being looked at more from the outside, and radio stations, venues [and] publications are aiding the local scene.”

The rapper’s insight highlights something that is distinct in a multitude of artists from the area: an independent, DIY approach to creative expression. This element of creativity is something that has further expedited Milwaukee down the path of musical recognition and imbued the city with a distinct character.

In addition to his own work, WebsterX harbors a refined and intriguing taste in art. Highlighting some of his current choices in music and film, the artist stated, “Musically I’m into Blonde by Frank Ocean, Injury Reserve’s Floss project, Playboi Carti’s tape, Syd’s Fin, Sampha’s Process and DAMN. by Kendrick Lamar, but then again that changes each day. I always tell people to pay attention to my Soundcloud ‘likes,’ too, to see what I’m listening to. My taste in film really boils down to indie films, horror, coming-of-age films, documentaries and the occasional chick flick. My favorite films are the ones that are shot well, look ahead of their time visually or think ahead of their time. As you can see, I’m into lots of different things in my life.”

In a climate of perpetually evolving sound, WebsterX has asserted himself as an ingenious, thoughtful and inspiring force in the rap scene. The artist’s career will surely evolve in upcoming years, as he garners more momentum each day, expanding the preexisting network of connections that have been made with artists who will help shape the future direction of contemporary hip hop. In essence, WebsterX exhibits a refreshing sense of open-mindedness and innovation with his music, contributing content that is pensive and impactful to the rap community.


William Emmons
Will is an Artsweek Editor. In his free time he enjoys listening to Death Grips and having heated discussions about the legitimacy of astrology.