Intangible heritage deemed worthy of preservation is often regarded as traditional culture that reflects the identity of a particular nation or group. Traditional cultures are distinct from commercial forms, which are transmitted and promoted via businesses, commercial establishments, and media. Research on culture reveals the way that a large part of the world's intangible heritage includes practices that interweave tradition and commodification as well as blur the boundaries between nations. As these practices do not fit into the clear categories of "traditional" or "national", they may not be considered for preservation in official project documents such as the Convention for the Safeguarding of the Intangible Cultural Heritage (2003), by the United Nations Educational, Scientific and Cultural Organization (UNESCO). Many of these practices are being, nonetheless, stored today through the unofficial archiving of moving images on the Internet, facilitated by Web 2.0. Through the case studies of various Caribbean performing arts, this paper illustrates how cultural research can provide a comprehensive understanding of intangible culture in both its lived and digital contexts, knowledge that in turn challenges the process of categorization and the measures of preservation of intangible heritage proposed by UNESCO.