Nelly & Flo Rida

A savvy rapper with crossover appeal, Nelly seemed like a novelty when he debuted with the Top Ten pop hit “Country Grammar (Hot…)” in 2000, but he quickly proved to be a legitimate hitmaker with “Hot in Herre,” “Dilemma,” and “Shake Ya Tailfeather” — and those three only account for a fraction of his Hot 100-topping and Grammy-winning hits. These feats built the foundation of a career that boasts six consecutive Top Ten albums, from the diamond Country Grammar (2000) to the platinum 5.0 (2010) and “The Fix” (2015), leading to warmly received collaborations in the 2020s.