Cultural continuity between home and school has been emphasized in a range of research concerning diversity and multicultural education [Colombo, M. (2005). "Reflections from teachers of culturally diverse children." "Young Children, Beyond the Journal," 60(6). Retrieved from http://www.journal.naeyc.org/btj/200511/ColomboBTJ1105.asp]. However, research that examines ways Hip Hop culture can be conceptualized as "play" in early childhood contexts is dismal. This dearth of literature regarding Hip Hop play suggests that Hip Hop play may not be regularly occurring or documented in early childhood classroom/learning settings. However, we do know that when culture is bridged from the home of some children to their schools, and when children experience positive outcomes academically and personally. This paper explores the possibilities of Hip Hop culture as "play" as an approach for nurturing children's development, cultural competence, cultural identities, and individual identities; and the power dynamics of teaches choosing to "allow", sustain, and "support" Hip Hop play.