This study investigates Hip Hop rap and R&B artists' use of monsters and characterizations of monstrosities in their lyrics. It examines Hip Hop rap and R&B artists' lyrics to determine the presence or absence of Afrocentricity and cultural linguistic resignification. Using Afrocentric method and a qualitative interpretive analysis of lyric's contextual meaning, findings suggest Hip Hop rap and R&B artist's lyrics containing monsters and characterizations of monstrosities is Afrocentric and culturally resignified. A further in-depth review of data also suggests the first semantic shift of references to monsters and monstrosities occurred through White hegemony's resignification of the terms and their meanings as a tool for pejorative reference and oppression. Hence, the Hip Hop generation has reclaimed the references to monsters and characterizations of monstrosities as an affirmation of positive regard.