Calboy’s colorful, inventive, and emotion-stoking approach to melodic rap goes back to the South Side Chicago native’s childhood. Born Calvin Woods in 1999, he first fell in love with visual art. He spent most of his free time painting and drawing, while absorbing music that was strongly expressive regardless of genre: Michael Jackson, 2pac, and pop-punk like New Found Glory. So when he found his way to hip-hop, Calboy was inspired to incorporate harmonizing into his delivery—and also to bare all. After teaching himself to produce, he released his breakthrough mixtape, 2017’s Anxiety, a sonically brooding set that delved into his struggles with mental health as well as the impoverished upbringing that exacerbated them. But it was 2018’s contemplative “Envy Me”—about making it to the other side—that marked Calboy’s arrival as a fully realized artist, his distinct vocal style perfectly matching the way he swirls up street hardness with a softer vulnerability. He expanded that approach to an array of topics on 2019’s Wildboy, especially with “Adam & Eve,” a trap love song about a blissful relationship gone sour. By 2020’s Long Live the Kings, Calboy was flowing freely between introspective and materialistic, and bringing others with him, from money-minded OG Yo Gotti to Chicago hotshot G Herbo. Whether he’s emoting deeply or purely stunting, Calboy sounds assured, never wavering no matter his circumstances or the company he keeps.
BORNApril 3, 1999