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.
Born Charles Edward Davis, Chuckyy was raised in the South Side of Chicago, more specifically the Low End. Expelled from high school, he began pursuing mus...