The Chicago rap scene is facing another legal setback as rising drill artist Chuckyy has been arrested on alleged weapons possession charges. The 20-year-old rapper, whose legal name is Charles Edward Davis, was taken into custody in the Cook County area on Tuesday, June 23, according to official arrest records obtained by XXL.
Currently, Chuckyy is being held in a Cook County jail without bond. While specific details regarding the circumstances of his arrest have not been disclosed, 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 standout talent within Lil Durk‘s Only The Family (OTF) imprint. His association with the label grew following a pivotal year for the collective, marked by Durk’s historic Grammy win for his contribution to J. Cole’s “All My Life.” Since then, Chuckyy has solidified his position in the Windy City’s competitive drill scene with a string of successful tracks, including “My World,” “Me vs. Me,” and “Lamb Chop.”
Despite the ongoing legal challenges facing his mentor, Lil Durk—who has been embroiled in a high-profile murder-for-hire case since late 2024—Chuckyy has remained focused on his creative output. Last year, he released his project Bloodbathh Vol. 2: Violate We Demonstrate and has continued to push his career forward with consistent visual releases.
In an interview with XXL earlier this year, Chuckyy spoke candidly about the guidance he has received from Durk. “A lot of this sh*t that he said a while ago still help me now,” Chuckyy noted. “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.'”
As the legal process unfolds, the industry remains watchful of how this arrest will impact the trajectory of one of Chicago’s most promising young voices.
