Calvin Lashon Woods, known professionally as Calboy, emerged from the Chicago suburb of Calumet City to become a breakout rap star in the late 2010s, propelled by the massive success of his quintuple-platinum single "Envy Me." Born on April 3, 1999, his music often blended melodic, emotive vocals with gritty street narratives, carving out a space within the hip-hop landscape that resonated with a wide audience. His career trajectory, marked by a major label deal and charting projects, established him as a notable voice from his region.

The rapper's journey into music began as a creative outlet during a challenging youth. He started recording songs in a makeshift home studio, initially distributing his music through social media platforms like Instagram. This grassroots approach built a local following and caught the attention of industry figures. His early tracks showcased a raw, melodic style that would become his signature, leading to his first official releases and setting the stage for his breakthrough.

Calboy's career exploded in 2018 with the release of "Envy Me." The track became a viral sensation, eventually peaking within the top 40 of the Billboard Hot 100 and earning a quintuple platinum certification from the RIAA for moving over five million equivalent units. The single's success was a defining moment, leading to a record deal with Polo Grounds Music, an imprint of RCA Records. Capitalizing on this momentum, he released his debut EP, Wildboy, later that same year. The project debuted at number 30 on the Billboard 200, a strong commercial showing that solidified his arrival on the national scene.

Following his initial success, Calboy remained prolific, releasing a string of singles and collaborations. He worked with artists like Lil Durk on the track "Brand New" and joined forces with Meek Mill for "Chariot." In 2020, he delivered his second EP, Long Live the Kings, which featured guest appearances from Young Thug and YBN Nahmir. While the project entered the Billboard 200, its performance was more modest compared to his debut. He continued to release music independently and through his label, including the 2021 project Black Heart and subsequent singles, maintaining a steady connection with his core fanbase while navigating the evolving music industry.