Lil Wayne

When Lil Wayne debuted as a 12-year-old kid on The B.G.’z 1995 album True Story, it wasn’t exactly clear that he’d become one of the best rappers of his generation. It’s not just that he’s clever or funny—it’s the way his style manages to balance classic, boast-driven rap with the kind of wild metaphors and constellatory thinking often left to poets. A native of New Orleans (“That’s why I holler ‘Hollygrove’ on each and every song,” he raps on Tha Carter II’s “Fly In”), Wayne (born Dwayne Carter in 1982) started writing rhymes at eight or nine, attracting the attention of Cash Money Records co-founder Bryan “Baby” Williams by freestyling relentlessly into Williams’ voicemail. After joining the short-lived but influential Hot Boys with fellow Cash Money rappers Juvenile, B.G., and Turk, Wayne launched an instantaneously successful solo career, exploring his ever-evolving lyricism while moving further into the mainstream, turning out a dizzying string of albums and mixtapes in the 2000s that were as radical as they were popular, his Tha Carter series most notable among them. In 2005, he managed to find time to start Young Money Entertainment, signing Nicki Minaj and Drake before most people knew their names. Beset by legal troubles (including a one-year sentence at Rikers Island), health issues (including an epilepsy diagnosis), and disagreements with his label, Wayne had a rough start to the 2010s but barely slowed down, releasing a steady stream of albums and mixtapes—including full-length collaborations with T-Pain and 2 Chainz—that continued to mine his seemingly endless imagination. Even if he made good on his periodic threats to retire (he called 2018’s Tha Carter V his last studio album but he followed with 2020’s Funeral and 2025’s Tha Carter VI), the fallout from his impact is everywhere, from Young Thug to Migos to Tyler, The Creator and Chance the Rapper—anyone who zigs when the rest zag.