Country and proud of it, Nappy Roots formed in 1995 around a sextet of students attending Western Kentucky University in Bowling Green. Four members of the group were Kentucky natives (Skinny DeVille, B. Stille, Ron Clutch, and Big V), bolstered by a pair of Oakland-born transplants (R. Prophet and Milledgeville).

Nappy Roots began making music together at a local record shop-cum-studio named ET's Music, and released their full-length debut, Country Fried Cess, in 1998. Drawn to the group's distinctive twist on Southern bounce, the major labels began flocking, and they eventually signed to Atlantic.

Their first album on Atlantic was 2002's biggest selling hip-hop album, "Watermelon, Chicken & Gritz". The multi-platinum album featured the hit-singles "Headz Up", "Awnaw", and "Po' Folks". The "Awnaw (Remix)" ft Marcos of P.O.D. appeared on Madden 2003. and the follow-up, Wooden Leather, arrived one year later. After several delays, the group released its anticipated album The Humdinger in August 2008; it was the first not to feature R. Prophet, who had left the group to pursue a solo career. Their second album as a quintet, The Pursuit of Nappyness, was issued two years later.

The group has sold over 5 million records, has 2 Grammy nomination, 1 MTV Video Music Award nomination, 2 American Music Award nominations as well as a Soul Train Award nomination.