Calboy

Chicago rapper Calboy looked to his own struggles with mental health and substance abuse when writing some of his hardest-hitting rhymes. Going so far as to name one of his mixtapes Anxiety, his songs loom heavy with moody melodies and huge trap beats. Several singles such as “Can’t Tell” paved the way for new fans, but it was the 2018 single “Envy Me” that broke through to millions with a viral video. Calboy’s reputation grew over the next few years thanks to mixtapes like Wildboy and the 2020 EP Long Live the Kings.
Calboy was born Calvin Woods in 1999. He was raised in the gritty South Chicago neighborhood of Calumet City, growing up amid crime and violence. This hostile environment would influence his music early on, with lyrics reflecting both the tough conditions of street life and the anxiety and depression he felt because of it. He formed a crew of artists and friends called the Paper Gang and set about working on music both solo and with this collective. His first mixtape, The Chosen One, was released in 2017 and was followed months later that same year by a second, Anxiety. 2018 brought the brief ten-song mixtape Calboy the Wild Boy, released on Paper Gang. While working on his next project, Calboy dropped the single “Envy Me” in September of 2018. The song caught on in a massive way, being streamed millions of times within its first few months of release. The buzz surrounding Calboy, the song, and its place in a burgeoning scene of melodic rap coming out of Chicago, was enough to land the rapper a major-label deal with RCA. In 2019, the Wildboy mixtape was assembled around the song, and included features from Lil Durk, Young Thug, Polo G, and others. Rounding out the year with the G Herbo-assisted “Purpose,” Calboy kicked off 2020 with the February EP Long Live the Kings. With further features from Lil Baby and Lil Tjay, the project saw the rapper continue to develop his melody-driven style. An assortment of singles appeared in early 2021 including the Lil Wayne collaboration “Miseducation.” ~ Fred Thomas