Chicago rapper and producer Caleb James is only 22, but he’s already been on a gold record—the thing is, it came out when he was 12. His father, Steve “Stone” Huff, who’s now a pastor at Safe House Church in Evanston, used to be a full-time musician and producer, and as a kid James would hang out during sessions at his dad’s West Town studio, Stone Recording. “Bump J used to be there, and I used to sit on his lap,” James says, obviously enjoying the image of a hard-ass Chicago street-rap icon getting chummy with a kid. That was how he ended up on a song with Bump and Cleveland R&B singer Avant—James was ten years old when he sang the chorus of “Flickin’,” a bonus track on the 2003 Avant album Private Room, which peaked at number 18 on the Billboard 200 and went gold in 2004.

“I thought The Jones was an amazing project,” Barber says. “I listen to it nonstop. To me that project was 2013 jiggy music—like Caleb was a jiggy artist that somehow was preserved until the twenty-teens.”

Given this environment, James’s career choice wasn’t a big surprise to anybody—he’d been trying to rap since he was seven. “I never wanted to grow up and be a lawyer or anything,” he says. “I always wanted to do music.” His dad encouraged him (“I’ve been behind him from day one”), but it was rough going at first. “I remember when he couldn’t rap on beat,” Huff says. “He wanted to rap, but he was so off beat.” Within a couple years James developed a knack for rhythm—he had access to all sorts of instruments at the studio, so he started learning the drums at age nine, played a bit of guitar in middle school, and picked up the bass as a high school freshman.

Huff has helped James through everything, doling out fatherly wisdom and, once A&R people began calling, career advice. “That’s my best friend, that’s my homie,” James says. “We talk every day. He doesn’t care if I cuss or anything. I can just be cool around my dad.”