Show & Prove: Chuckyy
Words: C. Vernon Coleman II
Chuckyy has a voice that commands attention. So, it almost seems like fate that after rapping for only about a year, the 19-year-old Chicago native was being courted by the self-proclaimed “The Voice,” Lil Durk, and Alamo Records, the label Durkio is signed to. To make things even more serendipitous, Chuckyy inked a deal with Alamo sister label Santa Anna Records in the first quarter of 2024, but he remains closely affiliated with Durkio’s Only The Family imprint. A bond that solidified the night that Durk won his first Grammy Award that year.
“He could have did anything [that night] for real, but he pulled up on us,” Chuckyy says of his first meeting with Durk. “That was the start of the journey.”
The established rapper’s hunch about Chuckyy seems to be spot on. In the past three years, Chuckyy has quickly risen as one of the Windy City’s latest drill rap wunderkinds, raking in millions of streams with tracks like “My World,” “We Got Buttons,” “Free Smurk OFNG” and others. He’s also garnered a cult following with his horrorcore aesthetic and prolific output.
Before the fame and A-list cosigns, Chuckyy’s journey began in the rough-and-tumble Altgeld Gardens neighborhood on the Far South Side of Chicago. Born Charles Edwards, Chuckyy attended Thornridge High School before dropping out around 10th grade.
“It was like too many fights was piling up,” Chuckyy recalls about the end of his scholastic career. “And then they tried to throw some bullsh*t on my name and say I was like a gang leader. That’s when I started rapping.”
Inspired by the likes of Lucki and Chicago drill rap godfathers Chief Keef and Lil Durk, Chuckyy made use of his uniquely guttural baritone and began recording raps on his phone in early 2023. He released his first song, “What They Gone Do,” by mistake.
“I bought an app that I thought I could just like wire it up on Instagram, but it actually dropped on all platforms,” Chuckyy shares. “It was doing numbers. It had like a half a million [streams] when I checked in like two months.”
Following the favorable snafu, the then-neophyte rhymer started releasing music independently on DSPs throughout the rest of the year, including singles like “Bail Out!” “Drench,” “Omerta” and the five-song EP BackfromdaDead.
By early 2024, Chuckyy’s music was picking up motion in Chicago’s rap scene. Through mutual ties with Durk, Chuckyy landed a meeting with Only The Family artist Chief Wuk, who told the upstart rapper that OTF was looking to sign new talent and Chuckyy was on their radar. Following Durk and Chuckyy’s Grammy night hangout a short time later, Chuckyy would sign a record deal with Santa Anna. Despite not signing with Durk, Chuckyy still waves the flag for OTF. “It’s like one hand wash the other, type sh*t,” Chuckyy maintains.
With a record contract in hand and a cosign from one of hip-hop’s biggest stars, Chuckyy wasted no time cranking out new material. He released the project Tweak Til the End in August of 2024, and followed it up two months later with Bloodbathh Vol. 1.
“I still haven’t paid for studio time to this day,” Chuckyy explains, shedding light on his recording process. He prefers the comfort of recording tracks at home.
Last August, the rising rhymer released his full-length debut album, I Live, I Die, I Live Again. The project features guest appearances from Lucki, Rob49 and Veeze and contains the well-received Bugg-produced single “My World.” After initially going viral on TikTok, Chuckyy earned his first entry on the Billboard Hot 100 with the song when it debuted at No. 79 on the chart last May. The track, which samples Canadian singer Ekkstacy’s “I Walk This Earth All by Myself,” has over 34 million streams on Spotify and over 26 million YouTube views for its accompanying music video.
Bloodbathh Vol. 2: Violate We Demonstrate dropped on Halloween 2025, and was accompanied by a short slasher-themed film of the same name that featured Chuckyy as a revenge-hungry rapper who takes out his detractors. He delivered the music video for the Track “F Talkin” shortly after the project arrived.
Chuckyy’s A&R, Jacob Gilliland, cites the bubbling rapper’s work ethic and “reinvention” as some of the traits that separate him from the pack. “[Chuckyy gives] the fans a consistent flow of music, without oversaturating,” Gilliland conveys. “He has a very distinct point of view and pays attention to every detail. Nobody in a long time has come out of Chicago with the level of versatility that he has shown in the last two years. He is a 19-year-old artist whose fans already recognize different ‘eras’ of his career.”
In the midst of Chuckyy’s rise, Lil Durk was arrested in October of 2024, for an alleged murder-for-hire plot. He has pleaded not guilty and, as of press time, is awaiting his trial in April. In Durk’s absence, Chuckyy has been drawing from previous jewels from Smurk.
“A lot of this sh*t that he said a while ago still help me now,” Chuckyy says. “He the reason that I probably ain’t broke right now. He was the one that was in my ear telling me…’Don’t buy that. Don’t do this.’ Or if I do buy it, he’ll come reimburse me. He ain’t even got to do no sh*t like that. We both grown. So, I f**k with bro. Free bro. That sh*t gonna work out.”
Despite his mentor’s legal issues, Chuckyy’s career is moving full steam ahead. With four projects released in two years, he plans to keep fans flooded with more content. Last Christmas Day, he delivered the project (//ChuckyyLostFiles//). Earlier this month, he unleashed another new video for “Kobe,” a track on Bloodbathh Vol. 2: Violate We Demonstrate. The momentum continues.
His big plans for this year include more music, features—namely a collab with Lil Uzi Vert—and a tour. Aside from rap, Chuckyy is also prepping a clothing line inspired by his uncle, set to arrive in the coming months. With 2026 shaping up to be another busy 365, he may be short on time, but he’s definitely not slight on hubris.
“I don’t even want no flowers out this sh*t,” he expresses. “A lot of people got their rap deals off my sound. I’m on y’all a*s. Y’all got to break me off. No cap.”
No more child’s play.
Listen to Chuckyy’s Bloodbathh Vol. 2: Violate We Demonstrate Album
