Chartbreaker: Calboy on His Chicago Rap Roots and Avoiding 'The Sunken Place'

In person, rising Chicago rapper Calboy is quiet and reserved, thoughtfully choosing his words in conversation before he fully commits to opening up about his story. But when he hops on stages throughout the U.S. on his first headlining tour, which kicked off Feb. 8, he exudes a youthful energy that grows explosive when he performs his Billboard Hot 100 hit, “Envy Me.” Says the 19-year-old: “I've got music in my soul. Ever since I can remember, music helped me through everything.”

Born Calvin Woods, Calboy grew up on Chicago’s South Side playing Guitar Hero and Rock Band and listening to Lil Wayne, 2Pac, Michael Jackson, All-American Rejects and local legend Chief Keef. But it was his father and cousins trying to break into hip-hop that led him to do the same. True to his Generation Z status, the rapper watched YouTube videos in middle school to learn how to record himself and mix music. “I took the computer and torrented all the programs like Pro Tools,” he says. “Then I started practicing my vocals.”

In 2016, Calboy uploaded his songs to Instagram, YouTube and SoundCloud through Paper Gang Inc., the indie imprint he formed with his mother. She was initially hesitant to the idea of her son entering the rap world, but soon changed her tune once she recognized his hustle and dedication. “[My mom] just texted me saying how proud she is,” the rapper says. “Can't nobody see your vision how you see your vision. You got to force them to see it come to life.”

Lucy Hewett
Calboy photographed on Jan. 28, 2019 in Chicago. 

Two years later after forming Paper Gang Inc., Calboy caught the attention of Polo Grounds Music founder/CEO Bryan Leach and label A&R rep Gwop. He signed a deal last October, joining A$AP Rocky and Pitbull on the roster. He has since made fans out of G Herbo, Lil Baby, Moneybagg Yo, Meek Mill, Rae Sremmurd and Chance the Rapper, who visits him in the studio (they both participated in Chicago Public Library’s YOUmedia youth program). “I used to look up to bro,” says Calboy. “Now I see videos of him turning up to my songs.”

One of Calboy’s songs in particular has propelled him into the mainstream: “Envy Me,” the street anthem that hit No. 41 on the Hot 100. Calboy waxes introspective throughout the catchy, JTK Pro Beats-produced beat about fighting demons and being “raised in the deep end.” The inspiration behind the lyrics, he says, derived from the Academy Award-winning film Get Out. “[“Envy Me”] is like being in the sunken place. My brother made me think of it that way. He told me, ‘I see that you’re in a dark place all the time. You can’t sink.’”

After losing friends at a young age and seeing classmates go to jail, Calboy is now prioritizing his physical and mental health. The first step for him was to quit using Xanax, a drug that continues to rattle the rap world. Lil Peep died from an accidental fentanyl-Xanax overdose in 2017, while Lil Xan (who was addicted to the drug for two years) checked himself into rehab last December.

“I’ve noticed that all of those drugs are downers. I would take them to make me feel better, but they weren’t really doing that. They were bringing me lower,” says Calboy. “I was constantly going to the doctor and getting stomach pumps, messing myself up all the way. I had to get myself up out of that.” Inspired by his grandmother, he turned to the Bible and the Quran for guidance. Now, the rapper claims his mental health is stronger than ever.

Lucy Hewett
Calboy photographed on Jan. 28, 2019 in Chicago. 

He now paints with watercolor and acrylic in his spare time and is currently working on a science fiction book, which will he hopes to publish within a year. The rapper also dreams of opening a franchise restaurant, likely soul food (“because every city we go there’s no good food,” he says), an idea sparked by his mother, who’s a chef. But as his music career continues to take off, his spare time is dwindling.

This spring, he’ll drop an as-yet-untitled follow-up EP to last June’s Calboy the Wild Boy mixtape, which he promises will be his best yet, owing to the energy from his momentum. “Remember when Goku [from anime series Dragon Ball Z] was a baby with a tail? Then, when he got older, he went into a different phase?” he asks. “I’m leveling up like Goku! I changed so much, I can’t go back.”