By Rose Miami 
HangupsMusic.com – Chicago, IL – In the dynamic and ever-evolving landscape of hip-hop, a new voice is emerging from the Windy City, commanding attention with a raw, distinctive sound. Chuckyy, a 19-year-old artist from Chicago’s South Side, has rapidly ascended the ranks of the drill rap scene, leveraging a potent blend of guttural vocals, prolific output, and a captivating horrorcore aesthetic. His journey from a neighborhood upbringing to a burgeoning music career, marked by a significant co-sign from rap mogul Lil Durk, showcases a unique trajectory fueled by talent and serendipity.
Chuckyy’s sonic identity is immediately recognizable. His deep, resonant baritone lends a gravity to his lyrics, setting him apart in a genre often characterized by higher-pitched flows. This vocal prowess, coupled with his relentless work ethic, has propelled him to millions of streams with tracks like "My World," "We Got Buttons," and "Free Smurk OFNG." His artistic vision extends beyond mere auditory appeal, embracing a horror-themed aesthetic that has resonated with a dedicated fanbase, cultivating a cult following that eagerly anticipates his frequent releases.
Born Charles Edwards, Chuckyy’s formative years were spent in the Altgeld Gardens neighborhood, a setting that undoubtedly shaped his perspective. His early academic career at Thornridge High School was cut short around the tenth grade, a decision influenced by the pervasive atmosphere of conflict. "It was like too many fights was piling up," Chuckyy has recalled, "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." This challenging environment, rather than hindering his creative ambitions, served as a catalyst, igniting his passion for music as an outlet and a means of expression.
The inspirations behind Chuckyy’s sound are deeply rooted in the Chicago drill scene, citing luminaries such as Lucki, Chief Keef, and of course, Lil Durk. These artists laid the groundwork for a generation of rappers, and Chuckyy absorbed their influence while forging his own distinct path. His initial foray into music creation was almost accidental. In early 2023, while experimenting with recording on his phone, he purchased an application he believed would facilitate simple Instagram uploads. Instead, the software inadvertently released his first track, "What They Gone Do," onto all major streaming platforms. To his surprise, the accidental release garnered significant traction, amassing half a million streams within two months.
This unexpected success spurred Chuckyy to embrace his newfound path. Throughout the remainder of 2023, he independently released a string of singles including "Bail Out!," "Drench," and "Omerta," culminating in the release of his five-track EP, BackfromdaDead. His burgeoning momentum caught the attention of industry players, and by early 2024, his name was circulating within Chicago’s rap circles. A crucial connection was made through mutual acquaintances, leading to a meeting with Only The Family (OTF) artist Chief Wuk. Wuk informed Chuckyy that OTF was actively seeking new talent, and that he was firmly on their radar.
The pivotal moment in Chuckyy’s career arrived shortly thereafter, serendipitously coinciding with Lil Durk’s first Grammy Award win. It was on this celebratory night that Durk, despite the monumental occasion, made time to connect with Chuckyy, solidifying their burgeoning relationship. "He could have did anything [that night] for real, but he pulled up on us," Chuckyy reflects, underscoring the significance of that encounter as "the start of the journey." This meeting paved the way for Chuckyy to sign a record deal with Santa Anna Records, a sister label to Durk’s primary label, Alamo Records. While not directly signed to OTF, Chuckyy maintains a strong affiliation, describing their bond as a symbiotic relationship, "one hand wash the other, type sh*t."
With a formal record deal in place and the invaluable backing of Lil Durk, Chuckyy accelerated his creative output. The year 2024 saw the release of his project Tweak Til the End in August, followed by Bloodbathh Vol. 1 just two months later. His recording process is remarkably self-sufficient; Chuckyy reveals he has yet to incur studio costs, preferring to craft his music in the comfort of his home environment.
His full-length debut album, I Live, I Die, I Live Again, arrived in August of 2025, featuring collaborations with notable artists such as Lucki, Rob49, and Veeze. The album’s Bugg-produced single, "My World," gained significant traction after initially going viral on TikTok. This viral success translated into chart performance, with "My World" marking Chuckyy’s debut on the Billboard Hot 100, peaking at No. 79. The track, which cleverly samples Ekkstacy’s "I Walk This Earth All by Myself," has amassed over 34 million streams on Spotify and over 26 million views on its accompanying music video, demonstrating its widespread appeal.
Continuing his prolific streak, Chuckyy dropped Bloodbathh Vol. 2: Violate We Demonstrate on Halloween 2025. The project was accompanied by a slasher-themed short film of the same name, in which Chuckyy portrayed a revenge-driven artist. The release was further supported by a music video for the track "F Talkin’." His A&R, Jacob Gilliland, highlights Chuckyy’s exceptional work ethic and his ability to consistently reinvent himself as key factors in his success. "He has a very distinct point of view and pays attention to every detail," Gilliland notes. "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."
The hip-hop community faced a significant development in October 2024 with Lil Durk’s arrest on charges related to an alleged murder-for-hire plot. While maintaining his innocence and awaiting trial, Durk’s legal situation has created a void. In his absence, Chuckyy has found solace and guidance in the wisdom Durk previously imparted. "A lot of this sht that he said a while ago still help me now," Chuckyy states, acknowledging Durk’s instrumental role in his financial stability and decision-making. "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 sht like that. We both grown. So, I f*k with bro. Free bro. That sht gonna work out."
Despite the challenges faced by his mentor, Chuckyy’s career continues to accelerate. He delivered the project (//ChuckyyLostFiles//) on Christmas Day and recently released a new video for "Kobe" from Bloodbathh Vol. 2. Looking ahead, Chuckyy has ambitious plans for 2026, including further musical releases, collaborations with artists like Lil Uzi Vert, and a highly anticipated tour. Beyond music, he is also preparing to launch a clothing line inspired by his uncle. With an unwavering confidence and a clear vision for his future, Chuckyy is determined to leave an indelible mark on the music industry. "I don’t even want no flowers out this sht," he asserts. "A lot of people got their rap deals off my sound. I’m on y’all as. Y’all got to break me off. No cap." The era of child’s play is officially over for this rising Chicago star.