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WOES | CHICAGO ARTISTS TO WATCH RECAP

Woes is a 30-year-old Chicago-born alt/rap artist redefining what it means to move independent. After falling out of both high school and college while studying music, he turned rejection into fuel—finding his voice by challenging authority and leaning into the realities of systemic oppression as a young Middle Eastern artist.

A true product of the city, Woes credits Chicago as his real education. He’s built his name through a relentless DIY approach, rejecting industry politics in favor of raw, unfiltered expression. Whether it’s performing in the streets, climbing billboards, or turning everyday spaces into stages, Woes has become known for his “by any means necessary” mentality and guerrilla marketing tactics that demand attention.

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Blending punk, rap, and indie influences—from Rage Against The Machine to Destiny’s Child—Woes delivers a sound that’s aggressive, emotional, and unpredictable. His artistry isn’t about fitting in—it’s about forcing people to look, listen, and feel something real.

Q&A WITH WOES (May 2025)

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  • When you first started your music journey, where was your confidence level?
    • I didn’t have any confidence. I was reading YouTube comments, and the most popular one said, “Kill yourself, white boy.” That made me realize I needed to get better.
  • Who was your biggest inspiration while growing up?
    • Musically, The Roots, Black Thought, Common, and Rage Against the Machine.
  • Did you ever want to give up in the process?
    • No, I never wanted to give up rapping.
  • What would you say is something you need to work on as an artist?
    • Communication & making sure everyone on my team is on the same page from start to finish.
  • At what point did you decide to take your musical career seriously?
    • I always knew I wanted to do it, but after high school, I realized it was the only thing I truly cared about.
  • Where do you see yourself in the future?
    • Hopefully alive and continuing to do what I’m doing now, just on a higher level. I just want to keep creating things that feel dope.
  • What was the process of creating your last project?
    • It was very thought out. A friend helped me narrow down about 16 songs into a final project by cutting what didn’t fit and shaping it into an album.
  • Are you seeking to secure a record deal or remain independent, and why?
    • I’ll do whatever it takes to do music full-time. As long as I can keep creating, I’m open to either path.
  • What are your favorite visuals that you have created and why?
    • The “Hyde” video. We had a group dressed as cops piling on top of me as a visual commentary. It was creative and impactful.
  • What is the highlighting moment in your career that encouraged you to do music?
    • Getting featured on DJBooth and seeing thousands of people engage with my music.
  • Do you write your own music?
    • Yes.
  • Do you think having a ghostwriter is beneficial to artists?
    • I write most of my music, but I have someone who helps refine it and holds me to a high standard. That kind of input is valuable.
  • Would you be interested in collaborating, and if so, who?
    • Common.
  • Are there any specific Chicago artists that you would like to work with?
    • Common.
  • What is your favorite thing about being an artist?
    • Freedom of expression. Nobody can take that away.
  • What’s an exclusive fun fact about you?
    • I can fight.
  • What is a guilty pleasure of yours?
    • Fighting.
  • What never fails to make you smile?
    • Fighting.

HIGHLIGHTS AFTER MAKING ARTIST TO WATCHLIST

  • Delivered a standout Audiotree Live Session in 2025, showcasing his high-energy performance style and genre-blending sound.
  • Performed at SXSW 2025, hitting multiple showcases and even doing guerrilla-style pop-up performances.
  • Known for unconventional live performances, including rapping on moving trucks and using creative props on stage. 
  • Released visuals and singles like “Kneecaps” tied to his project Pressing My Luck, continuing his creative rollout. 
  • Built a reputation for a genre-blending sound mixing punk, rap, and indie influences, helping him stand out in Chicago’s underground scene.  
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