Naughty By Nature's self-titled debut was released in 1991 and produced an inescapable Top Ten hit in "O.P.P." They repeated their success with the 1993 follow-up album, 19 Naughty III, which produced another ubiquitous crossover smash in the "hey! ho!" chant of "Hip Hop Hooray"; the album hit the Top Five and, like its predecessor, went platinum. 1995's Poverty's Paradise went on to win a Grammy for Best Rap Album.

Black Sheep recorded one of rap music's most entertaining debuts, A Wolf in Sheep's Clothing. "Flavor of the Month," and "The Choice Is Yours" were major hits.