For an album to be considered one of Lil Wayne’s most essential works is a tall order; after all, this is a guy who’s released no fewer than 50 mixtapes, albums, and EPs. But the rapper’s 2008 mainstream breakout, Tha Carter III, makes a nearly unequivocal case for Wayne’s most commercially and critically successful offering to date. Most importantly to his career, Tha Carter III cemented for the mainstream what the underground already knew to be true: That Wayne possessed not only unparalleled lyrical prowess, but also an undeniable commercial sensibility. Enlisting a laundry list of hit-making producers—including Kanye West, Swizz Beatz, Play-N-Skillz, and the late Static Major—the rapper and label-head strived to make an album that would appeal to radio, but that wouldn’t sacrifice his signature ingenious wordplay. The resulting album is among Wayne’s most focused: Though West reportedly gave 20 instrumentals to Wayne, the New Orleans rapper told him to “slow down,” and only used three of West’s tracks (including “Let the Beat Build” and “Comfortable”). The 16 songs that did find their way on Tha Carter III include a few love-centric cuts, like “Mrs. Officer” and the Babyface-assisted “Comfortable”—both of which went on to become instant classics. Still, it was the success of Tha Carter III’s trio of early singles—“Lollipop,” “A Milli,” and “Got Money”—that skyrocketed Wayne to global popularity, and helped earn the rapper his first Grammy wins. Wayne claims to be ambivalent about Tha Carter III, even going so far as to say the album “holds no significance” for him. But to fans and critics, the album stands as a mid-2000s masterpiece—a record that, even if just for a moment, backed up Wayne’s claim of being the best rapper alive.