It’s October 26 and a steady stream of people is trickling in and out of Pilsen’s inconspicuous Low Pressure gallery. Well-known street artists like Afrokilla and local brands like Uprise are selling their wares. Taco trucks are selling to a swelling crowd of smokers and skaters outside. Inside, someone is selling beers in Solo cups tapped from a keg, near a half-pipe painted like a pack of Newports.
Once the crowd has gotten fed and buzzed, Woes takes the stage. He performs directly beneath a bespoke mockup of an old ice-for-sale sign that reads: “IT’S A COLD WORLD OUT THERE” and “ICE SOULED HERE.” The venue and stage are a fitting tribute to the DIY space and to his lyrics: Heartbreak, the prospect of death, escapism, delivered with wordplay and an unfeigned hatred for the police.
Backed by a live band of collaborators, Woes’ raps get a rock treatment reminiscent of Rage Against the Machine and System of a Down—which is apt, since Serj Tankian and Woes share a proud Armenian heritage. (Woes’ Instagram profile even sports the Armenian flag.)
From the jump, the energy in the small space is tangible. The crowd sings along and moshes. One particularly unruly fan has to be reminded a few times to calm down. Others mention how they drove from the suburbs to catch his set. But after the show, Woes’ night is just getting started. He encourages the crowd to purchase merch so he can get gas money for a road trip to New York. Some of those fans give him cash without buying a thing—a vote of confidence in his come-up.
In New York, he promotes his new album, Pressing My Luck, with shows, a podcast appearance, and guerilla messages on LED construction road signs. The DIY tactics are nothing new for him. Last summer, he pulled up outside Lollapalooza and Riot Fest in a box truck with some friends and performed. Once, he says, he got a call with Def Jam by pretending to be his own agent.
For our interview, I asked him to pick a spot that held personal significance. Woes suggested we meet at Chris’ Billiards, a forty-one-table pool bar in Portage Park made famous by Martin Scorsese’s The Color of Money.
“I’ve been coming here for so long,” said Woes, who grew up in the south suburbs and now lives on the North Side. “It was always a place that I could just kind of, like, exist in.”
Pressing My Luck, like Woes’ other projects, features a team of collaborators and producers including Goodboy, Hobbes, The Kid Rated R, and DJ Sun. (“I hear rappers that are like, ‘I produce and I mix and I master and I do this myself.’ It’s like, well, good for you!” he joked.) Fitting enough, we were joined by long-time collaborator Bless 1, who produced some of Woes’ earliest work (including an early breakthrough, “Grandkids,” which Woes remembers hearing on Vocalo for the first time while driving Lyft). Miles Kalchik, another collaborator and musician in his own right, shot pictures.
We played cutthroat, a three-player version of pool, and talked about Pressing My Luck, how it came about, the process of songwriting, and where Woes got his start in music.
The following conversation has been edited for length and clarity.
What inspired this latest album?
Being in danger, honestly. And putting myself [in danger], like, literally. There’s not a hidden message. It’s called Pressing My Luck because that’s probably what I’ve done since I moved here as an adult [and] for the last, like eleven years. When I moved to Chicago, back to Illinois. Just playing with fire and poking the bear and just [doing] dumbass shit.
How’s the reception been?
I’m grateful that it’s been received in a very good way. Which also is hilarious, because you make music and nobody hears it for a long time. At least, that was my fucking experience, and nobody hears it. And then you think in your head, like, how do you get people in front of your music, you know?
How did you start releasing music?
SoundCloud. I literally started fucking with releasing music, like, as a kid. I posted it on Yahoo! Answers. Yeah, literally posting it in, like, you know, Reddit threads and Yahoo! Answers and commenting on YouTube videos and being like, “I rap too, check [me] out, man.” Literally just on the Internet, anywhere that I could post a link. I’d be like, “let me know what you think of this.” And a lot of people were like, “Kill yourself. This is horrible.” You know? And I was like, I gotta get better at this. This sucks. I’m not made for this. The online comments. I would post that shit like crazy on Tumblr. I fell in love on Tumblr and that shit.
Who were your influences?
I take influence from graffiti homies. There was a lot of graffiti homies at that show. They do what the fuck they want to do, whenever the fuck they want to do it, and they live their lives exactly how they want to. I take influence from them. Dave Chappelle of, like, how to frame a line you know what I mean? How to talk to people, Black Thought and the Roots, you know what I mean? Like, listening to The Roots, they were huge for me in terms of influences too.
But I grew up listening to Destiny’s Child and Aretha Franklin. Like, my mom would play all sorts of [music] and my dad would play classical music and Armenian music. Like, the oud and a drum called a dhal, which is a drum that you play between your legs. I don’t know if I would say that it was an influence, but more just a subconscious feeling I got as a kid, of listening to music that made you want to move. You know what I mean?
You also have a couple of videos up, right?
Yeah, we put a bunch of videos. That was the biggest thing last year that I realized that what made people pay attention is almost not even about the song. I throwaway song that I would write one verse to. And then we’d go out and we’d think of a cool visual. And then I went to one of my old mechanic homies and was like, “you have a pile of tires in the back of your shop,” and he let us shoot the video in the back of it during the Puerto Rican parade. And it’s just like that, thinking about visuals that are actually intriguing and make people interested.
How long have you known that you wanted to do music?
This is the only thing that I’ve ever loved, making music and making this shit. It’s been the only thing that I’ve ever cared about. And the only thing where I’ve ever felt fulfilled in a sense where I was like, why would I do anything else? Like, I’m doing it now, and I’m just gonna keep doing it until I can make a living from it.
Clocking in at 30 minutes and 58 seconds, Pressing My Luck is available on all platforms for streaming and purchase.
Francisco Ramírez Pinedo is a journalist based in South Chicago.