The documentary describes the ascension of West Indies cricket from being a team largely composed of highly talented, entertaining, "Calypso Cricketers" to a determined unit that dominated world cricket for almost twenty years.

It begins with an introduction to the West Indies Cricket Team. Using interviews with West Indian cricketing greats, and other people closely associated with West Indies cricket; this idea of culturally and politically different Caribbean nations playing under the common banner of the West Indies is described.

The history of cricket in the West Indies is briefly described, such as the appointment of Sir Frank Worrell as the first black man to captain the West Indies Cricket Team, and the emergence of such cricketing greats as Everton Weekes, Learie Constantine, and Sir Garfield Sobers. However talented these individual cricketers were, they were unable to fetch results, resulting in the West Indies being perceived as "Calypso Cricketers"; people who were entertaining, but would eventually lose.

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