Kanye West, The College Dropout (2003)

Label: Roc-A-Fella, Def Jam

At a time when super hero rap was the hot ticket, here came a kid from Chicago rocking pink Polo shirts with popped collars who was rapping about how bad he felt for all the clothes he bought. Behind those rhymes weren't slick keyboard synths, but warm, lovingly chopped soul samples that played like a mix between the RZA and Diddy's Hitmen crew. Kanye was able to bring the best of the underground to the forefront and infuse it with pop sensibilities.