In the past century, the multiple Caribbean islands that form part of a culturally diverse region called the West Indies were settled by many Europeans such as the British, Danish, Dutch, French, Portuguese, and Spanish. The Caribbean region has not been the subject of much management research. We focus on one of the countries in the region, Barbados, and use an emic approach to analyze and understand the culture and its implications for the workplace. In the past thirty years, Barbados has grown to become a leading international centre in the Caribbean. We use the metaphor of Calypso music to examine Barbadian culture along some of the popular cultural dimensions used in management research. Music is an integral part of the West Indian culture and Calypso is a rich tool to examine Barbadian culture in particular.