Chuck Strangers grinds on his own terms.

photo retrieved from Spotify.


On May 19th, 2023, an hour before his set at Sleeping Village, a bar in the Avondale neighborhood of Chicago, 31-year-old rapper-producer Chuck Strangers sits in the corner of the tiny green room, rolling a blunt. There are five other people in the room: a scrawny roadie posted up near the door and a quartet of guys in hoodies on a dingy coach that runs from wall to wall. We all sit around a table strewn with ornamental flowers and weed crumbs, the scent wafting through the air. The door creeps open and a head pops in through the gap. Strangers looks at the head in anticipation. 

“What’s it look like out there?” he asks. It’s the second stop on a seven-city tour, and his new EP The Boys & Girls has only been out for a week. Chuck’s concerned about the audience turnout. There’s a moment of silence.

“Better,” the head says blankly. 

“Better? What’s better?”

“10–15 people.”

“Oh, okay, whatever,” Chuck says while nodding, somewhat satisfied. 

An hour later, I stand in the audience and watch Chuck peek out from the side of the stage with a stressed grin on his face. It’s a slightly larger turnout than expected, but it’s not enough to fill out the venue, the backroom of a spacious bar in Avondale. Twenty or so people stand waiting, their faces occasionally illuminated by a disco ball hanging in the middle of the room. Everyone seems to be holding a drink, and there’s a disproportionate snapback-to-head ratio. A thick layer of smoke hangs above the crowd, filtering the rays of green that beam out from the stage. Songs by underground rap royalty, namely Billy Woods and Mach-Hommy, rattle out of the speakers, the drumlines stuttering through the room. 

Suddenly, the music cuts off. The stage lights transition to a purplish-blue. The crowd starts clapping and hooting. Chuck lumbers onto the stage, crowned with a NY logo cap. He's wearing a short-sleeve button-down with an oversized undershirt. It drapes below his waist and covers the beltline of his baggy jeans, making his legs look like stubs compared to the rest of his body. Two gold rings gleam off of his right hand, one of which looks like a Native American face in an iced-out headdress. Chuck’s face stands out in contrast to his clothing. He’s got a bushy Baron Davis-esque beard and wide eyes that seem to pop out of his head as they dart around the ceiling.

“I go by the name Chuck Strangers,” he rumbles into the microphone. A wave of violins washes out of the speakers, swallowing the room. High-pitched glissandos dip in and out of the murky string swamp, and a low bass note drones in the background. Nobody in the crowd dances, but everyone starts bobbing their heads to the music, creating a steady heartbeat of nods. Chuck keeps his eyes glued to the ceiling as if he’s trapped underground, searching for a sliver of sunlight. Lyrics spill out of his mouth: 

“I put my head down all 82 games…”

It’s an opening line that epitomizes Chuck Strangers’ inexorable work ethic. He’s like an NBA player who’s going all out for an entire season. As a rapper-producer, Chuck’s constantly trying to improve both his songwriting and his beatmaking. “When I'm sitting there looking for samples for four hours and don't find one, it’s just a grind. I go to the studio some days and don't make shit,” he admits during our interview. In his lyrics, he often equates the labor of a musician to the training of a disciplined athlete. “Burn comes with getting reps in,” he declares on the opening track of The Boys & Girls. When I mention his frequent comparisons between music to sports, he nods. “I'm always rapping about sports. It's the same to me.”

Chuck sees tonight’s concert as both a part of the grind and an opportunity to grow. “Doing shit like this. Coming out here. We trying to build it, you know? One day, I'm planning to be able to start selling shit out. We're gonna go out there and kill it for whoever decided to pull up and just keep going.” 

The small turnout seems a little sad at first, but the show feels much more intimate as a result. Chuck banters with the crowd throughout the performance, and he even plays a bunch of new music for us. After the sinister piano riffs on “Venison” fade, a guy with an out-of-place jaw shouts, “That beat was amazing. Did you produce that?” Chuck shakes his head and says, “Nah, that was Annimoss.” The guy’s mouth drops. “Annimoss?” he squawks in disbelief. I imagine this crowd might be one of the few in the world that knows Animoss, the producer behind Ka’s Orpheus vs. the Sirens. A couple of songs later, Chuck looks at his DJ and nods, giving him the cue to cut the music. “Man, y’all are so amazing… I feel blessed tonight. Imma just play some unreleased shit for y’all, y’know, the shit that I like,” he says, the sweat glistening off his temple. He laughs, and adds, “I feel like I’m here with my family.”  

Chuck’s real family didn’t always approve of his musical ambitions. His parents are Grenadan immigrants who moved to Flatbush, a neighborhood in Brooklyn. Throughout his childhood, Chuck remembers his parents playing reggae and soca records in the house. When he started making beats in high school, his parents encouraged it as a pastime. However, when they realized that Chuck wanted to pursue music as a career, they had other ideas. “They were supportive of me making music, but they thought it was just a hobby of mine,” he says.  

His parents kicked him out of the house late in his teenage years, and was “scared initially because I thought I was gonna be homeless, but thank god my friend Patrick let me stay at his place. And it turned out to be a blessing because I could make music all the time.” His time couch-crashing his friend’s apartment turned out to be an important moment in Chuck’s early musical career. He joined Pro Era, a rabble-rousing NY hip-hop collective with an old-school flavor, and started making beats for a young Joey Bada$$. He produced four of the songs on Joey’s 2012 project 1999, a release that’s since been hailed as one of the greatest mixtapes of all time. Strangers has a couple of features on it as well, most notably on “FromdaTomb$.” His voice bounces over an airy sample from the video game “L.A. Noire,” warning against the perils of hedonism and bragging about his beer-pong prowess. 

Chuck Strangers’ music in 2023 is completely different. Samples still abound in his beats, but they move slower, and the lush instrumentals sound more expansive. His shit-talking attitude on the mic has since been replaced by something more subdued. It’s particularly noticeable in his live performance. At times, the music overwhelms Chuck’s husky voice, and it can be difficult to make out the words. His stage presence is similarly understated. He spends most of the show in front of the mic stand, occasionally meandering around the stage like he’s rehearsing lines. Every couple of songs, he stands statuesque with his eyes closed. When the beat starts, his hands begin to caress the air, as if he’s preaching a laid-back sermon. But the words are more confessional than inspirational. As Chuck trudges across the stage, the Latin sample of “Suydam St” croons in the background. The red stage lights follow him as he raps, “Money fleeting faster than it’s coming in. / Lord willin’ we see the sun again, I’ll know to cherish this warmth.” 

His lyrics reflect the adversity that comes with being an underground artist. His early brushes with success didn’t launch him into any sort of stardom. While Pro Era gained traction, Chuck moved out to L.A., which stifled his productivity. He admitted that “from 2014 to 2017, I wasn't even really making a lot of music. I was depressed. I used to wear Birkenstocks and the same pink shirt until it got dirty and I didn't even care.” Even after putting together two solo projects in 2018 and 2020, Chuck found it difficult to sustain his love for rapping. He claims, “I fell out of love with rap because I wasn't getting money from it. I make my living primarily through producing songs for other people." 

And yet, here he is, promoting a brand new EP, getting his reps in. Some publications have touted The Boys & Girls as Chuck reigniting his passion for rapping, and he agrees: “All kinds of stuff is happening in my life… turbulence, if you will. So recording was an outlet to make sense of all that shit.” Like many artists, Chuck’s creative process is therapeutic, and the results are at times gut-wrenching. On songs like “Benevolence,” he gives himself a half-hearted pep talk: “I’m praying for a sign, never lost faith, just one day at a time.”  

Chuck still has a long way to go. His live show is underdeveloped, and it smacks of inexperience. Early in the set, the jubilant vocal samples of “Dettol” begin to blare out the speaker. Chuck raps four bars of his verse and then starts to mumble. “I’m sorry y’all. Lemme start this over,” he says, laughing awkwardly. The beat loops back and Chuck raps the first four bars again, only to make the exact mistake. “I can’t believe this is happening,” he says, shaking his head in disbelief. “Alright, we’ll just go to the next song.” 

Despite these setbacks, Chuck never loses the crowd’s support. It’s in part due to his willingness to engage with the audience. Before performing the unreleased “Basic Economics,” Chuck gives us a preface.

“So basically, this song is about how the whole concept of economics is evil. Like why do we need that shit?” 

“Yessir!” shouts a voice from the other side of the room.

“Yo Chuck, these samples are crazy and fuck Jeff Bezos!” shouts the guy standing next to me.

“Right! Thank you!” Chuck responds, extending a hand toward him. 

These kinds of exchanges are littered throughout the show, and it’s clear that each of the 20 something people in the room have his back. It’s very easy to root for an artist like Chuck Strangers. He could easily make a living off of beats for other rappers, but he’s committed to creating projects of his own. His refusal to compromise his artistic integrity may sound exhausting, but Chuck couldn’t imagine doing anything else. “I just like to make music. That’s literally what I do for fun. I get the same joy from making beats that a n**** would get from playing Xbox or some shit like that.” 

The Boys & Girls lacks commercial appeal, as it’s largely devoid of catchy hooks. In fact, it’s mostly just rapping. It’s hard to imagine it charting, and I wonder how Chuck balances his honest creative expression with monetary incentives. Backstage, I ask him if he hopes that touring will bring some financial stability. He nods his head. “Yeah, I'm gonna do it my way though,” he says. “I'm not going to pander or nothing to make some bread.” 

Halfway through the show, Chuck performs “Prospect Park West.” He wanders between me and a stage light, and the details of his face blur into a shadow. His head looks like a silhouette as he raps, and a purplish glow radiates off of its outline. He tilts his head towards the ceiling, and he seems triumphant, though I can’t see his facial expression. I hear his voice booming, “I knew the sun would rise in time, celebrate the grind.” 

It sounds as if the grind is finally over, but if his hard-nosed ethos is anything to go by, Chuck won’t stop anytime soon.


edited by Kristen Wallace, Copy Editor.

photo retrieved from Spotify.

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