He began writing songs at age 4 and was introduced to music by his father, who was also a hip-hop artist. In fact, they co-wrote an album, titled Father-Son Talk, when he was 11. Lil Skies released his first mixtape, Alone, in 2017, and it yielded the singles “Red Roses” and “Off The Goop.” The rapper released his first major label mixtape, Life of a Dark Rose, in 2018. It debuted at number 23 on the Billboard Hot 100 and peaked at number 10.