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.”