Q&A With Milwaukee Musician WebsterX

In advance of his Turner Hall release show, we talked to WebsterX about his new record, its dark, real-life inspiration, the pressure to release a full-length album and whether he would leave Milwaukee.

Over the past few years, the Milwaukee rap scene has undergone a renaissance. The city now boasts a robust cadre of strong emcees. Much of the thanks should go to WebsterX and his music collective New Age Narcissism, who have done wonders to change the perception of hip hop in the city with their unwavering optimism and emphasis on the team.

The music videos of WebsterX have also played a major role. The projects—which are directed by Cody LaPlant and Damien Blue—are stunningly beautiful and cinematic, displaying an amount of precision that bleeds into WebsterX’s songs. He’s also trying to pay things forward by setting up a better foundation for the next generation with the monthly all-ages music series he co-founded, FREESPACE.

On Friday, May 26, WebsterX celebrates the release of his new album, Daymares, with a performance at Turner Hall Ballroom. The occasion can’t help but feel like a victory lap for the city’s rap scene. In advance of the show, we talked to Webster X about his new record, its dark, real-life inspiration, the pressure to release a full-length and whether he would leave Milwaukee.

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You’ve said you went through a rough time after the release of your first full-length project, Desperate Youth. Instead of focusing on the bad stuff, what kept you going through this period?

Well I did focus on the bad stuff, a lot, which is what kept me in that place for a while. In reality, though, I was simply 21 and just learning new things and scared to fail. Only things that kept me going during that time period was the success that freaked me out post Desperate Youth, my girlfriend Siren, my supportive friends, my sister and these dreams that refuse to leave my brain.

Do you find the process of writing music therapeutic?

Most definitely, closure is what it provides.

You repeat “I don’t wanna be dark” on the album opener “Nightmares.” You’ve mentioned that you had an initial project titled Daymares ready back in 2014, but you scrapped it because you thought it felt rushed and too dark. Why did you feel it was important to come at the album with a more positive angle?

Well, I knew the positive angle was important because most people are not trying to listen to a super sad album all day and if they are it’s because they might want to justify those feelings through the music. I’m not that type of music consumer, though. Sad music just makes me more sad when I’m sad.

I’m also not really that type of person really. People usually view me as a high energy positive guy which a smart person would know can never 24/7 be the case. The reason why I spoke about this period in my life is because I found it inspiring, I’ve never felt anything like that before, depression or anxiety, or at least fully understood what it was which made me think about it more thus making it worse.

For me, “Tick Tock” feels like a song where come to terms with taking things a little slower. Did you feel pressure to release another full-length shortly after Desperate Youth? How did you overcome that anxiety?

Yup, “Tick Tock” is clearly all about the concept of time. I wanted it to be as obvious and as straight forward as possible. ‘Boy i’m tryna beat the clock/ Please somebody make it stop/ Time might just be all up’ then the combatting positive ‘And boy I ain’t stoppin for nothing/ Stop these daymares from coming.’ Essentially saying I’m not stopping for anything, anxiety included. No matter how sad or weird I felt about life I knew I’d overcome it eventually and here I am today.

I most definitely felt pressure to release a full-length after Desperate Youth and even more so the longer it took, but for the last four months I really worked on the album full-time it was easy to block that all out especially when I dropped ‘Blue Streak’ as the first single.

You weren’t exactly sedimentary between albums–in fact, quite the opposite. You organized the monthly FREESPACE series, been a part of the collective New Age Narcissism, released several singles and an EP and premiered some breathtaking music videos. Do you think working with filmmakers Cody LaPlant and Damien Blue on your videos impacted the way you approach your songs on Daymares? If yes, how so?

Totally, for the simple fact that even before Cody and Damien I’ve always been inspired by how music and film coexist, my music reflects that. I also want to act and have my music in movies which has already slightly manifested in ways, it’s the shit.

The one song that always jumps out to me on Daymares is “Underground.” It feels like a love letter to your time in Milwaukee. Do you ever envision yourself leaving here and moving to a larger city?

“Underground is that exactly. I totally do want to leave, you need to, you need to experience new stuff but don’t abandon the place that made you, you. I want to rent Airbnb’s in different cities for months at a time, mostly Los Angeles and New York City and make my next works out there. I have a lot of growing relationships in each city and people want me there. My long term goal is having a home in Milwaukee and then being able to travel and rent Airbnb’s months at a time across the world.

What’s your preferred medium: music video, single, album or live show?

You’re gonna make me choose? They all couldn’t exist without each other! But shows for sure, hands down.

Not many Milwaukee artists are able to draw enough to host album release parties at the spacious Turner Hall Ballroom. What can people expect from the show?

Overall, I’m just very geeked to be able to do this, for real, but people can expect one of the most engaging shows they’ve seen in the 414 area code in a while. If they miss it, they can relive it through word of mouth and the internet.



Kevin is a freelance writer residing in Milwaukee. He’s contributed to The Shepherd Express, Third Coast Daily, Pop Matters and the sadly now-defunct A.V. Club Milwaukee. He looks forward to forging a deeper connection with the city’s impressive music scene during his gig as a Music Notes blogger. His talents include music criticism, riding a bicycle, drinking tasty beers and a crafty croquet swing. His weaknesses comprise Jean-Claude Van Damme movies, professional wrestling and his ever-growing record collection. He’s in desperate need to find more physical (and hard drive) space for the exceptional albums Milwaukee musicians keep churning out.