At just 21 years old, Chicago’s J.R. Donato—born Demetrius Gordon, Jr.— already has more than eight years in the rap game under his belt. But this isn’t just eight years of hallway freestyles and playground ciphers: by the time he reached his twenties, J.R. had already been mentored by hometown hero Twista and signed by Wiz Khalifa to his Taylor Gang label. From swiping his dad’s Tupac CDs out of the family car to begging his grandma for a copy of Get Rich or Die Trying for Christmas, JR was surrounded by music at a young age in his hometown of Waukegan, just north of Chicago.