Caleb James (right) and his father, Steve “Stone” Huff, at Safe House Church in Evanston, where Huff is a pastor
Caleb James (right) and his father, Steve “Stone” Huff, at Safe House Church in Evanston, where Huff is a pastor Credit: Adam Jason Cohen

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.

That’s not to say James had a career at that point. He didn’t start recording his own music till summer 2011—a couple years earlier, he’d become a member of the Save Money crew, alongside Chance the Rapper and Vic Mensa, and his first song was “Pay Back Is a Dog,” which featured a verse from Mensa and production from James and ThemPeople. He released it on his first mixtape, Ground Up, in summer 2012, and then solidified his identity as an MC in July 2013 with the follow-up, The Jones. That second mixtape is stacked with euphoric party tunes perfect for soundtracking summer days that don’t end till the wee hours, and it borrows liberally from 90s hip-hop and R&B. The slow-burning, squealing synth melody on “6 AM” is one of several elements James nicks from Snoop’s “Gin & Juice,” and when he half-sings the chorus on “No Go” over a fonky, jagged synth line, he sounds like Puff Daddy on “Can’t Nobody Hold Me Down.”

Andrew Barber, founder of Chicago hip-hop blog Fake Shore Drive, points out that Puff Daddy (aka Sean Combs, aka Diddy) did the same sort of thing when he ruled the charts, incorporating bits of popular songs that were old enough for people to feel nostalgic about—on “Can’t Nobody Hold Me Down” he combines bits of Matthew Wilder’s “Break My Stride” and Grandmaster Flash & the Furious Five’s “The Message.”

“That’s exactly what Caleb is doing,” Barber says. “He’s taking sounds that were popular 15 or 20 years ago.” James makes them his own, fusing them into his shimmering, feel-good hip-hop. The Jones has lots of entry points—I got drawn in by James’s easygoing, likeable personality and cool confidence, the melting wah-wah guitar and sweet singing on “24’s,” and the unidentifiable croaking, stuttering sample on “Flexin’.”

“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.”

That borderline anachronistic sound helps James stand out, but idiosyncrasy has its disadvantages. Up-and-­coming local rappers often end up forced to define themselves in terms of whoever or whatever is big in their town, whether or not their music has anything to do with it—think about all the upstart Chicago MCs who had to talk about Chief Keef or the drill scene in 2012. Fortunately for James, these days Chance the Rapper and Vic Mensa have come to stand for “new Chicago rap” in lots of people’s minds. Even though James doesn’t sound like his friends, they’re complex artists, hard to categorize—and listeners used to dealing with that will have an easier time approaching him with an open mind.

James heads down to Austin next week to perform at South by Southwest—among the concerts he’s got lined up is an official showcase with beloved Oakland hip-hop group Souls of Mischief, who are riding high on a 20th-anniversary reissue of their classic debut, 93 ‘Til Infinity. He’s also working on The Jones 2.0, which he plans to release shortly after SXSW.

Huff has been a guiding force in James’s rap career since before he had one. His own father, James’s grandpa, was the same way—though he was a construction worker, not a musician, he gave Huff his first instrument at age nine. “When I leaned towards music, he came home with a bass—just dropped it in my lap,” he says. Just before Huff turned 15, his father suffered a heart attack. “He passed away, but I had the instrument,” he says. “It’s taken me all over the world—on tour, and studios, and platinum records.”

Caleb James builds a beat with his laptop and a Native Instruments Maschine portable production studio.
Caleb James builds a beat with his laptop and a Native Instruments Maschine portable production studio.Credit: Adam Jason Cohen

Huff’s career in music has also taken James to lots of places—when his dad played bass on tours with Keith Sweat and R. Kelly, James went along, in the process getting introduced to many of the artists who now influence his sound. Huff set up Stone Recording when James was around ten. “I’d just kind of let him loose,” Huff says. “He’d come home from school, go into the studio, running around with the engineers, kind of turning knobs, pushing buttons.” James not only had the run of a multimillion-dollar studio, but he also got to meet his share of famous musicians and industry folks, including the Gap Band’s Charlie Wilson, Kelly Rowland from Destiny’s Child, and Kanye West’s manager Don C. “Back in the day, before Kanye got on, he’d sell my dad throwback jerseys,” James says. “Keke Wyatt used to babysit me when I was little.”

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.

James dropped out of school at 17—he’d been attending a charter called Pathways in Education on 87th—and started working at Dominick’s, the first in a series of odd jobs. “I got my own apartment, and I’ve been living on my own ever since,” he says. Around that time he befriended rapper Joey Purp and the rest of the Save Money crew, who would hang out out at streetwear boutique Leaders 1354 in Wicker Park—of course this was years before Save Money became the Chicago rap powerhouse it is today.

It was also before the September 2011 death of Rodney Kyles Jr., a friend of the crew who was fatally stabbed during a fight in Lincoln Park. Chance witnessed the killing; James didn’t see Kyles get stabbed, but he’d been hanging out with them that night and saw the rest of the tragedy unfold. “I was the first person to actually know that Rodney died, because when he got to the hospital I told them I was his brother,” James says. “I had to call his parents—I had to tell his parents what happened.”

Kyles’s death affected Huff too. “It was a defining moment for Caleb, and it was a defining moment for me—because it could’ve been him,” he says. “How do you really process that? That stays with you. He wept. He wept really hard, ’cause I know Caleb has a heart.” Chance processed his grief by pouring himself into his debut mixtape, #10Day, which he recorded at ThemPeople’s studio. “That’s when Save Money, the music, really started,” James says. “I was in the studio making my mixtape [Ground Up], Chance was in the same studio—that’s where he made #10Day. That’s where it all really began.”

Father and son
Father and sonCredit: Steve “Stone” Huff

Ground Up came out on James’s 21st birthday: July 15, 2012. It’s a strong debut, though it lacks the stylistic cohesiveness of The Jones. “I felt like I had to be a super ‘rappity rapper,’ like Vic or Chance,” he says. “I was like, ‘You know what? This isn’t really me. I feel like I’m trying to compete with somebody else or be better than somebody else instead of just being me.’ So I just started taking it in my own hands.” In fall 2012 he left his last day job (at Peeled Juice Bar on the near north side) and threw himself into making music full-time.

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.”

Huff had long wanted to be a pastor, but it wasn’t till after he saw the video for 50 Cent’s “P.I.M.P.” that he decided to leave his music-biz career for the church. “That whole entire record [Get Rich or Die Tryin’] just really was the epiphany that I had,” he says. “It let me figure out what I’m doing with my life.” Though he loved the music, its materialist message left him feeling spiritually starved, and in 2007 he finally made the switch.

Huff might never have returned to music if it hadn’t been for his son—his first visit back was collaborating with James on a couple tracks from The Jones, “Mr. Jones” and “Finesse.” But he’s game to do more: “If he ever calls me for work, I’m like, ‘When do you want to meet?'” At least one track they did together will appear on The Jones 2.0.

Even when he’s not working on a song with his son, Huff finds ways to help him with his music. James has enlisted some hot beat makers for The Jones 2.0—its sinister single “Eddy Curry” features production by Treated Crew duo Nez & Rio, who worked on The Jones and Schoolboy Q’s new major-label debut, Oxymoron. But his biggest coup has been to score a beat from veteran Chicago producer No I.D., whose work has appeared on platinum albums by Kanye West (Yeezus, My Beautiful Dark Twisted Fantasy), Jay Z (The Blueprint 2, The Blueprint 3), and Drake (Thank Me Later). James knows him through Chicago producer Xtreme, who came up alongside No I.D. and worked on The Jones. No I.D. made the track specifically for The Jones 2.0, but James has been sitting on it for more than two months—he’s found the prospect of recording his verses a little intimidating. Of course his friends have let him know what a great opportunity this beat represents, but it’s his father’s encouragement that finally gets him into the studio.

I meet James at Soundscape in West Town to watch him record. No I.D.’s beat (it’s part of a song called “We On”) is opulent and triumphant, and James seems eager to get started. He practices his first verse with Joey Purp, then charges into the booth. The first take isn’t right, though: “You sound like you’re chillin’,” says Purp. He tells James to try it again with more feeling, so before his second take James moves a music stand away from the microphone so he can wave his hands around as he raps. Purp stands in front of the booth’s window, sweeping his arms like a conductor whenever he wants James to land hard at the end of a line. James nails it. “No I.D. on the beat,” he raps. “My nigga, we made it.”