The charismatic Southern rapper Lil Wayne began his industry ascendance as one of the Hot Boys, a short-lived all-star group on Cash Money Records. After establishing himself as a successful solo artist, he grew to become a critical favorite, known for his confident boasts, entertainting underground mixtapes, and prolific output. Born Dwayne Michael Carter, Jr., on September 27, 1982, in New Orleans, LA, Lil Wayne grew up in the Hollygrove neighborhood of New Orleans' 17th Ward. There, he became acquainted with the Cash Money Records collective, which he eventually joined as a teenager. Get It How U Live! (1997), a Hot Boys album also featuring Juvenile, B.G., and Turk, marked Lil Wayne's album debut; at age 18, he was the youngest group member.

A second Hot Boys album, 1999's Guerrilla Warfare, arrived several months before Lil Wayne's solo debut, Tha Block Is Hot. The solo record went double platinum, peaking at number three on Billboard's album chart while spawning a Top Ten hit with the title track. Lil Wayne's second album, Lights Out (2000), failed to match the success of its predecessor, nor did his third album 500 Degreez in 2002. By this point, Lil Wayne was the only remaining Hot Boy on the Cash Money label -- all other members had defected -- and the future didn't seem promising for him or his label. Consequently, Lil Wayne purportedly scrapped work on his fourth album and instead released the recordings as an underground mixtape, Da Drought (2003), his first of many to follow.

2004's Tha Carter signaled a change in direction for Lil Wayne. The album itself wasn't a significant departure from Lil Wayne's past work -- after all, it was filled with tracks produced by Cash Money's in-house producer, Mannie Fresh, some of which could well have been left on the cutting room floor -- yet it showcased a more measured and mature performance by the rapper, who seemed newly emboldened and sported a new, dreadlocked look on the album's cover. Tha Carter spawned Lil Wayne's biggest hit in years, "Go DJ," while the album itself was a Top Five hit. 2004 also marked the beginning of Lil Wayne's string of guest appearances on other artists' songs, starting with Destiny's Child's "Soldier."

A pair of popular 2005 mixtapes, Dedication (with DJ Drama) and Suffix (DJ Khaled), further established Lil Wayne as a dexterous freestyle rapper. By the end of the year, Lil Wayne's reputation had significantly grown, and Tha Carter, Vol. 2 debuted at number two on Billboard's album chart upon its December release. In the wake of Tha Carter, Vol. 2, which was a critical favorite as well as a strong seller, Lil Wayne continued to bolster his resume and increase his fan base via the mixtape circuit. Of the myriad mixtapes bearing his name from 2006 onward, Dedication, Vol. 2 (DJ Drama, 2006) is a standout; like Tha Carter, Vol. 2, it was a critical favorite, making an appearance on many critics' end-of-year lists. The Carter, Vol. 2, Pt. 2: Like Father, Like Son (DJ Khaled, 2006) was notable, too, as some of its material was revived for 2006's Like Father, Like Son, a major-label collaboration with Baby, aka Birdman, that spawned the hit "Stuntin' Like My Daddy." Lil Wayne also collaborated regularly with Dipset member Juelz Santana during this period. After stolen tracks from his next official album appeared on the Internet, the download-only EP The Leak appeared in 2007. A year later, that same EP appeared as a bonus disc on a limited-edition release of Tha Carter III, which sold over one million copies during its first week of release. Fueled by singles like "A Milli" and "Lollipop," the album sold an additional million copies during the following month, making it one of the most popular albums of 2008. ~ Jason Birchmeier, All Music Guide