Gabby - Emmerton
The mighty gabby that is. A force of nature. To be as simplistic and reductive as possible, he is the Bob Marley of Barbados (without the world acclaim). A gut wrenching ode to the village he grew up in to start things off.
http://www.youtube.com/watch?v=NKBXCaqdObI

Rupee - Jump
This song only works if you have big bottle of Mount Gay Rum in your hand. Preparation is key.
http://www.youtube.com/watch?v=PdmC7j2cqf4

Red Plastic Bag - Something's Happening
Ah, Crop Over songs, how I love thee. "Moving to soca beat. All the women looking sweet." What else do you need?
http://www.youtube.com/watch?v=9TWF74tiWlo

Jackie Opel - You Send Me
Spouge music. Invented in Barbados. Why this isn't sung from the tops of all the coconut trees in the world is beyond me.
http://www.youtube.com/watch?v=EmLnQ5t4bZQ

Wendy Alleyne - Have A Thing About You
Ahhhhhhhhhhhhh.
http://www.youtube.com/watch?v=aAQ6cRXWzJA&feature=related

The Merrymen - Yellow Bird
I have mixed feelings about this song. Not so much the band (they're really annoying). But there's something wonderfully innocent about the way they do this song that's very endearing.
http://open.spotify.com/track/47J5oXNLexR8mUWwYxC6yS