Lil Wayne peaked with the release of “Tha Carter III,” fully realizing his braggadocious and clever wordplay with equally eccentric beats. The obvious big songs of the album are the singles “A Milli” and “Lollipop,” which still see endless play but under that is the Katrina ode “Tie My Hands” and underrated classics like “Dr. Carter” and “Phone Home.” this era would define Lil Wayne’s style, from his iconic laugh to his sunglasses and flat-brim hats. After releasing several free mixtapes over the year digitally, Wayne was on top of the digital space that was becoming the most important market for music in 2008. His music would inspire and inform the next decade of artists from Drake to Nicki Minaj.
One of the most interesting stories in rap, Lil Wayne started as a child prodigy in New Orleans, worked his way to the top of Cash Money Records before helping usher in a new era of hip-hop. He made rap mainstream and brought it to the digital age before crashing his career with mediocre music, foolish decisions and a legal battle with Cash Money while rising stars he mentored replaced his relevance like Drake and Nicki Minaj. But much like a prodigal son, Lil Wayne returned to his roots and made one of the greatest comeback records in rap history.