The anglophone Caribbean has long been celebrated and known for its vibrant and innovative music. Reggae, dancehall, calypso, soca, gospel and ringbang have flourished within the Caribbean and have exploded on the worldwide stage. This work deliberately moves away from the customary exclusive focus on Trinidad and Jamaica and broadens the discourse to represent the wider region. It addresses several topics which remain under-discussed in Caribbean music, such as the status of Caribbean gospel; the birth of new musical styles in the Eastern Caribbean; cultural misrepresentation in Caribbean music videos; the representation of AIDS in Caribbean music; and the impact of the actual music technology utilized by Caribbean musicians in the last twenty years.