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In 1991, at the age of nine, Lil Wayne joined Cash Money Records as the youngest member of the label, and half of the duo The B. Most of the group's success came with their platinum-selling album Guerrilla Warfare (1999) and the 1999 single "Bling Bling".

Carter has a tattoo dedicated to Rabbit, who was murdered before Carter became a star.Da Drought 3 was released the following year and was available for free legal download.It contained Lil Wayne rapping over a variety of beats from recent hits by other musicians.Carter recorded freestyle raps on Williams's answering machine, leading him to mentor the young Carter and include him in Cash Money-distributed songs. Near the release of Lights Out, Lil Wayne was featured on the single, "Number One Stunna" with Big Tymers and Juvenile, which peaked at No. Lil Wayne's third album 500 Degreez, released in 2002, followed the format of his previous two, with significant contributions from the Hot Boys and Mannie Fresh.He also recorded his first ever collaboration album True Story with rapper B. While being certified gold like its predecessor, Tha Carter II, the follow-up to the original Tha Carter album, was released in December 2005, this time without production by longtime Cash Money Records producer Mannie Fresh, who had since left the label.

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