Calboy Makes a Strong Case for Himself as Chicago’s Next Up

Show & Prove
Words: Peter A. Berry
Editor’s Note: This story originally appeared in the Winter 2019 issue of XXL Magazine, on stands now.

Calboy’s first recording sessions doubled as stealth missions. While in seventh grade, he would tiptoe to the desktop in his grandmother’s house, where he’d compete with 16 other live-in relatives for access to the computer. “I used to hide it,” the now-20-year-old rapper admits of the early, insecure phase of his music-making career. Millions of streams and a major label record deal later, it’s safe to say the secret’s out.

Born Calvin Woods, the South Side Chicago native has made a strong case for himself as the Windy City’s proverbial next-up. Cal made his debut in 2017 with his mixtapes The Chosen 1 and Anxiety, combining the pained, Auto-Tune-laced melodies of Lil Durk with vivid recollections of life in the trenches. While the latter project earned him exposure, his true breakout began in the summer of 2018. That’s when he unloaded “Envy Me,” a piano-driven single that eventually became his first platinum-certified record. “I never got 100,000 views before I got 1 million,” Calboy says of his pre-“Envy Me” YouTube track record. “I went from zero to 1 million, real fast.” Today, that view count exceeds 150 million, and Calboy kicks back in a brand-new Chicago spot he copped after making it big.

Cal has come a long way from his grandma’s cramped quarters, where he remembers a lack of privacy and having to boil hot water to take baths when the bills weren’t paid. Yet, being so close to his family gave him a sense of security. “The streets wasn’t that hard,” he conveys of his past. “I went to school with all my brothers and my cousins, so we ran the school because there was so many of us on the same team.” It was in his grandmother’s spot, years before signing a deal with Polo Grounds/RCA Records in October of 2018, that Calboy stayed up at all hours of the night teaching himself how to produce and record by watching YouTube tutorials. After perfecting his skills with Pro Tools and securing a $250 recording kit bought for him by his uncle, Calboy, who grew up listening to The All-American Rejects, Green Day and Paramore as much as he did J. Cole and Kendrick Lamar, began charging people $20 to record their albums. The $100 condenser mic he used for his earliest songs hung from a shelf in his closet.

While he’s far from an overnight success—Calboy rapped for at least six years before landing a record deal—his talent was evident from early on. His father was the first to notice and unsuccessfully tried to sign Calboy to his own record label. Later, other family members began paying attention. “One day I just played my music—I was like, 13—I played one of my first songs and they like, ‘Bro, what is this?’” he remembers. “I told them it was me and they were like, ‘OK, you sound great!’ Then I wasn’t scared no more to say nothing to nobody.

That’s when I knew I could do it serious when I was a shorty. But I knew it was going to take time for me to mature [and] develop. I already knew all of that, so I wasn’t in a rush.”

When he wasn’t playing AAU basketball for the Windy City Trendsetters, Calboy toiled away in the studio until it was time to put out his breakthrough project. That moment came after his second trip to a psychiatric ward. When he was a freshman in high school, he’d been diagnosed with an anxiety disorder, which he says was exacerbated by the trauma he experienced due to feeling misunderstood and seeing friends get killed. After the trip, he hit the studio and recorded the aptly titled mixtape Anxiety in just four days. Besides helping propel him to stardom, Anxiety pushed Calboy to shape his mission. “I just want my fans to understand that there is other folks outside of them or outside of their immediate circle that go through the same exact things that they go through,” he expresses. “I think my fans should take a little comfort from my music.”

While his lyrics are often filled with flexes and threats both implied or directly issued, some of his bars read like an instructional guide for survival. On “Ghetto America,” he rhymes, “On the grind, gotta get it, ain’t no feelin’ hopeless/I done been through what you been through, why you mopin’?/Had to take that risk and put my wrist in motion/I was young and reckless, I know that I’m older.”

After the release of “Envy Me,” everything began to change. In 2019, Calboy signed with Meek Mill’s Dream Chasers Management and landed a feature on Chance The Rapper’s debut album, The Big Day. He also hit the road with 21 Savage for the I Am > I Was Tour. Producer JTK, who laced “Envy Me,” attributes the rapper’s rapid rise to his relentless work ethic. “He was recording on the tour bus every day,” says JTK, who’s been working with Calboy since 2017. “And he versatile. I done heard him do some different things, from R&B to rapping. That’s gon’ keep him in the game.”

Calboy intends to do more than just keep afloat; his aspirations include landing a diamond plaque. But his goals aren’t all self-serving. Outside of music, he plans to buy a commercial space for a restaurant that employs his aunt and five of his cousins and open a tattoo parlor in Atlanta that will staff other family members. As for his fans, he wants to continue to inspire and pay it forward. “I get DMs all the time saying, ‘Your music helped me get out of depression’ or ‘Your music helped me with my anxiety,’” Calboy says. “Sometimes I text back. Sometimes I might give a little motivation back, give a little advice to an upcoming rapper that asked for it... It keep me warm, for real. Keeps you motivated. Shows you what you doing it for.”

Check out more from XXL’s Winter 2019 issue including our Travis Scott cover story, interviews with Moneybagg Yo Young M.A and Doja Cat plus Show & Prove features with Pop Smoke and Lil Tjay. 

See Photos of Travis Scott's XXL Winter 2019 Cover Story Photo Shoot