His career began in 1995, at the age of 12, when he was signed by rapper Birdman, joining Cash Money Records as the youngest member of the label. Formerly a member of the rap group Hot Boy$, he joined the Cash Money Records collective as a teenager. Get It How U Live, released in 1997, was Lil Wayne’s first album with Hot Boy$. From then on, Wayne was the flagship artist of Cash Money Records before ending his association with the company in June 2018. Regarded as one of the most influential hip hop artists of his generation by XXL, he has often been cited as one of the greatest rappers of all time.

In 1997, Carter joined the Hot Boys along with rappers Juvenile, B.G., and Turk. At age 14, Carter was the youngest member at the time. Hot Boys’ debut album Get It How U Live! was released the same year, followed in 1999 by the group’s major-label debut Guerrilla Warfare, which reached No. 1 on the Billboard Top R&B/Hip-Hop Albums chart and No. 5 on the Billboard 200. During their career, the Hot Boys had two charting singles, “We on Fire” from Get It How U Live! and “I Need a Hot Girl” from Guerrilla Warfare. Carter was also featured on Juvenile’s single “Back That Azz Up”, which reached No. 18 on the Billboard Hot 100 and No. 5 on the Hot R&B/Hip-Hop Singles & Tracks. Let ‘Em Burn, a compilation album of unreleased tracks recorded during 1999 and 2000, came out in 2003, several years after the group disbanded. It reached No. 3 on the Top R&B/Hip-Hop Albums chart and No. 14 on the Billboard 200.