Chuckyy

Chuckyy represents Chicago's South Side with his deceptively lackadaisical flow, disregard for traditional song structures, and favoring of productions that create a filmic sense of suspense. The fast-rhyming drill rapper broke through in 2023 with "What They Gone Do?" and two years later crashed the Billboard Hot 100 with "My World," the atmospheric third single from I Live, I Die, I Live Again (2025), his third mixtape. By the time of that tape's release, Chuckyy had signed with Lil Durk's OTF label.