Posted by Rising Chicago drill artist Chuckyy is currently facing significant legal challenges following his recent arrest in the Windy City. The 20-year-old rapper, whose legal name is Charles Edward Davis, was taken into custody on Tuesday, June 23, on alleged weapons possession charges.
According to an arrest record obtained from the Cook County Sheriff’s Office, Chuckyy is currently being held in a Cook County jail without bond. While specific details regarding the circumstances of the arrest remain undisclosed, his next court appearance is scheduled for June 29. Representatives for the artist and the Cook County Sheriff’s Office have been contacted for further comment.
Chuckyy has gained significant traction as a key figure within Lil Durk‘s Only The Family (OTF) imprint. His association with the label solidified in 2024, a landmark year for the collective following Durk’s Grammy win for the hit single “All My Life.” Since joining the roster, Chuckyy has established himself as a formidable force in the drill scene with tracks such as “My World,” “Me vs. Me,” and “Kobe.”
Despite the legal turmoil surrounding his mentor, who has been incarcerated since October 2024 on an alleged murder-for-hire plot, Chuckyy has maintained a rigorous creative output. He released his project Bloodbathh Vol. 2: Violate We Demonstrate last year and recently premiered the music video for his latest single, “Lamb Chop.”
In a February interview, Chuckyy spoke candidly about the guidance he received from his mentor, noting that the advice provided by the incarcerated rapper continues to shape his career and personal decisions. “A lot of this sh*t that he said a while ago still help me now,” Chuckyy shared. “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.'”