Bold, unpredictable, and fiercely unapologetic, Woes is carving a lane for himself in the music world with his genre-defying sound and magnetic persona. Chicago-based but universal in appeal, his art fuses punk’s raw emotion, rock’s grit, and rap’s intensity into an unpredictable, eclectic style that refuses to be ignored.
Press play on Pressing My Luck
With his latest 11-track project, Pressing My Luck, released October 25th, Woes takes his philosophy of embracing mistakes and diving headfirst into chaos to new heights. The album showcases his unapologetic outlook and the beauty of taking risks. Singles like “Cheaper By The Dozen,” “Kneecaps,” and “HIDE” stand out as bold testaments to his daring creativity. When asked about the project’s inspiration, Woes explains:
“I wanted to create something that’s a reflection of real life—messy, reckless, but also full of lessons. Sometimes, making the wrong decision is the only way to learn. ‘Pressing My Luck’ is me saying, ‘screw it,’ and jumping into the unknown, no parachute”.
Raised on an eclectic track-list that included Rage Against The Machine, Beastie Boys, Aretha Franklin, and Destiny’s Child, Woes channels his wide-ranging influences into his music, creating a raw, fearless sound that resonates with anyone seeking authenticity. It’s this fearless energy that makes him stand out in an industry often afraid to take risks.
Step into the sounds of Woes
In addition to Pressing My Luck, Woes has been turning heads with a string of striking singles, including “Hazmat,” “American Cheese” featuring Bless 1, and fan favorites “RAMBO” and “One Way” featuring Dunedogs. Each track highlights his ability to weave intense emotion with sharp, often darkly humorous lyrics, showcasing his versatility as both a lyricist and performer. Woes is a cultural force. When asked what drives his artistic intensity, he goes on to say:
“I’ve always been a person who doesn’t follow the rules. Whether it’s life or music, I’m not afraid to say or do what others won’t. That’s what I want my music to feel like—raw, unfiltered, and real”.
As fans dive into Pressing My Luck, they’ll find a body of work that’s as unpredictable as the man behind it—filled with raw emotion, rebellious energy, and an underlying message of embracing life’s messiness. Whether you’re headbanging, vibing, or deep in thought, Woes has a track that will strike a chord. With his unpredictable edge, audacious sound, and fearless attitude, Woes is pressing his luck—and it’s paying off. Are you ready to take the plunge with him?
If so, check out his candid interview with us here at REMIXD Magazine. The trailblazing talent delves deeper into the philosophy behind his music and his unapologetically bold persona. For now, following checking out our interview, get familiar with this rising rhymer by pressing play on Pressing My Luck.
Bringing it back to Woes humble beginnings
- Hey WOES! Thank you so much for speaking with myself on behalf of REMIXD Magazine. Before we jump into all things WOES, your artistic journey, Pressing My Luck & more! But, first – for fans new and old, can you tell us who WOES is and where it all began for you?
” I got the name from being in church a lot as a kid and communion when you ask for forgiveness for your sins, and then you say, ” Woe to me.” That joint. s: So that’s where I got it because I was always scared of sinning as a kid a lot. I was raised pretty religious. So then that kind of took the shape, you go through a bunch of names as a kid when you’re rapping and you go through a bunch of them and then this was the one that kind of stuck when I was 18. So cuz I always found myself rapping about s*** that was also just kind of sad real life s***. so it kind of was just sad s*** and that kind of is what I found myself just gravitating towards”.
- You’ve been described as “the sweetest asshole you’ll ever meet”. How do you balance that duality in your music and your persona?
I was raised closely by my grandmother, so she taught me the love that you need in life and I had the love of a woman, my father and my mother were also present but I lived with my grandmother and feeling like the love of her and then also being a kid in Chicago – you very much need to have a wall up. I mean, I don’t know if you need to… but that was like when I found myself, having to be hard regardless. I’ll help a old lady cross the street and the homie is also seeing me pop out on a biker that hit my mirror in the car, So, it’s kind of the duality of it”.
- Your sound blends punk’s raw emotion, rap’s intensity, and rock’s grit. How did your diverse influences, like Rage Against the Machine and Destiny’s Child, shape your unique style?
“I grew up in a house that was playing it all of the time. My father would play like Beastie Boys and my mother would play like Destiny’s Child and Aretha Franklin and then my brother at the time would play System of a Down, So it was all of the sounds. Yeah. I just heard it all. The first time I heard Lil Wayne was in a Destiny’s Child feature. I didn’t listen to Lil Wayne because I was super religious and my mother wasn’t like letting me buy rap CDs. everybody at school was buying 50 cents, “Get Rich or Die Trying” and I was like I’m not allowed to listen to that. So I think when I was introduced to music as a kid, I was paying attention to how it made me feel and that’s the same feeling I try to carry over to everything that we’re making now”.
- You’ve got a raw, bold aesthetic—if your life had a soundtrack, what would the first three tracks be?
“Probably Play That Funky Music by Wild Cherry and then 99 Problems by Jay-Z. And I don’t know for the third one – it could be like an Aretha Franklin song”.
About Pressing My Luck –
- The title of your project, Pressing My Luck, feels both daring and introspective. What inspired that name, and how does it reflect your journey as an artist?
“Probably going back to… what we were saying earlier of me not thinking and just reacting. Literally, I was on the phone with a guy Damon who called earlier and he’s a musician. He sings it and he’s been my parallel through all the music s*** and we were on the phone and I was going to call it ‘Trigger Warning’ to try to be tongue and cheek of being woke and being PC and all that s***.
And then we were talking and then I told him some story and he’s like, “How about you call the project ‘Pressing My Luck’ because you might die before this album comes out.” I was like, “All right, that’s a cool name.” And then it kind of just stuck. But it’s very much been like a motto of seeing how close you can get to the fire before getting burned”.
- Standout tracks like “Cheaper By The Dozen” and “Kneecaps” have fans talking. Can you share the stories behind those songs and what they mean to you?
” “Cheaper by the Dozen” was me rapping on s*** that didn’t think I should be or s*** I don’t think fit like I didn’t hear myself on it. So, I took it as a challenge and was like, let’s see what it would sound like if I force myself to write to it. And that just turned out to be one of my favorite songs and that kind of shaped that was the first song that I had of this new project. So that song has been done for three years and when I went to Baltimore for my producer to help me, he produced the whole thing. I played him “Cheaper by the Dozen” and another song called “Rambo” and I was like these two songs – I want these to set the tone of what this project is and the production that you hear are trap elements, but also we tracked live drums over Cheaper By A Dozen”.
- Your philosophy of “embracing mistakes and diving headfirst into the unknown” is bold. How does that mindset influence your creative process, both in the studio and on stage?
“If you trip on a mistake that you make on stage then you can f*** the whole show up. This guy sitting behind me Bless produced a bunch of songs but he produced the latest one “American Cheese” that was on this EP. And it’s like he was my biggest motivator to push me to be like, you need to perform live because it made me the most uncomfortable because there’s so much more room for error, You can sit in your house and work on a record for f****** three years and then never let anybody see you. But on stage, you just have to embrace everything. Nothing is perfect. People that are watching you perform don’t even know when you f****** up. And I’ve been on stage before and* up a bunch. And I’ve also been on stage before and gotten off and been like, that was cool, right? And then figuring out what you need to strengthen”.
- With 11 tracks, Pressing My Luck is a solid project. If someone could only listen to one track as an introduction to Woes, which would you recommend and why?
“Probably “Tunnel Vision”. I like that song a lot. But there’s every song I like for a different reason, but Tunnel Vision was another one. That song is years old and we saved it. I was like this I want to be on the project. It’s just honest”.
Genre-Fluidity and Experimentation –
- You seamlessly fuse multiple genres. How do you decide when to lean more into punk, rap, or indie in a particular track?
” It just depends on the feeling that’s the music is giving us. It starts with the music for sure. Then letting the music take it into whatever direction that it will be and being open to whatever that is. It could be a R&B song or it could have a rock element or it can just be like old school like an old Al Green sample, it can be whatever it is. And just being open to that and not trying to fight that. I think when you’re trying to fight s***, then you’re going to end up with some s*** that’s not you”.
- Experimentation seems to be at the heart of your artistry. Can you tell us about a time you took a creative risk that paid off—or one that didn’t?
“Everything is a learning moment. I used to write emails. I didn’t know how to send music to people. You know what I mean? I didn’t have anybody that was like, this is how you send an email or this is how you word an email. It’s like even that s*** of sending an email or sending emails to bookers or venues. You learn. I don’t know if you really want some s*** you’ll find a way to learn about it. I think that’s the biggest thing is realizing that of nobody owes you anything”.
Creative collaborations –
- Your collaborations on tracks like “American Cheese” and “One Way” showcase unique chemistry. What do you look for in a collaborator, and how do those partnerships enhance your sound?
“I look at voices like instruments, So if you got an acoustic guitar, it’s going to sound good with a bass guitar. So, obviously I got a deeper voice than he does. I like that contrast, of going back and forth, different sounds. So, that’s the first thing I kind of look at and in different styles, and just the fun thing is just like creating something that you wouldn’t be able to create as one person. Because you’re gonna get some different ideas to bounce off each other. Then you’ll have something that you definitely wouldn’t create just by yourself”.
- As someone who thrives on unpredictability, do you ever find challenges in aligning with other artists or producers who might not share your creative philosophy?
“Yeah, we go through that. Yeah, it’s like a tug-of-war, with different ideas because, you don’t think alike, which I think is actually a good thing though. Because you may not dig at first, but then you start to think about it okay, I like that. You know what I’m saying? That’s something that I never even thought about. You know what I mean? So, yeah, definitely we go through that a lot. You know what I’m saying? I’ll have some different tracks or whatever and I’m like, man, you need to jump on this.Woes: He like, “I don’t know.” You know what I’m saying? and vice versa. You know what I’m saying? I might be playing a beat and then I’m just skipping through it or something. He like, “What’s that?” I’m like, “No, this ain’t the one.” He like, “No, I like that one.” You know what I’m saying? So, yeah…”.
- If you could create a dream collaboration with any artist, dead or alive, who would it be and why?
About WOES philosophy and persona –
- You’ve embraced making the “wrong decisions” as a learning tool. Can you share a moment where a so-called “wrong decision” led to one of your greatest lessons or successes?
- Your music often feels unapologetic and fearless. How do you stay grounded while constantly taking risks and breaking norms?
“by the people you surround yourself with”.
- When you’re not creating music, where does Woes find inspiration? Do you have any hobbies or rituals that fuel your creativity?
“Just enjoying myself and having fun”.
What’s next for WOES?
- With Pressing My Luck out, what’s next for Woes? Any upcoming projects or collaborations fans should be looking out for?
“I really don’t know honestly. We’re going to SXSW in March. I’m not gonna say there’s more music or that we’re coming correct this year. That s**’s corny as f***. just put your money where your mouth is. There’s no big grand plan. We have an idea and then we do it and there’s just finding the next right step”.
- Lastly, is there a message that you’d like to leave with fans?
“Just do whatever the f*** fills you up and just do it for you. I don’t know. You can do anything you want to f****** do really. And that doesn’t mean anything to anybody else. That nobody needs to give a f*** about what you’re doing. You have to just do the s*** that makes you happy. And if that’s it, that’s ok because the only thing that matters is you being happy“.
CONNECT WITH WOES ON SOCIAL MEDIA:
INSTAGRAM | APPLE MUSIC | SPOTIFY | YOUTUBE
