Chicago rapper looked to his own struggles with mental health and substances when writing his hardest-hitting rhymes. Going as 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 the millions with a viral video.
Calboy was bor Calvin Woods in 1999. He was raised in the gritty neighborhoods of South Chicago, growing up amid crime and violence. His hostile environment would influence his music from early on, with lyrics reflecting both the tough conditions of street life and the anxiety and depression he felt from it. He formed a crew of artists and creators called the Wildboyz and set about working on music, both solo and within this collective. His first mixtape, The Chosen One, was released in 2017 and was followed months later with the second mixtape Anxiety. While working on his next project Calboy dropped Envy Me in September of 2018. The song caught on in a massive way, being streamed millions of times within the first few months of release.