This chapter deals with the interrelationships between forms of American English and Caribbean English and creoles, both past and present. Close demographic connections between the North American mainland and what was to become the Anglophone Caribbean have existed since the earliest days of colonial settlement. Later, American linguistic influence spread in the region through institutional links, occasional visits or migration by Caribbean nationals for work or education, and tourism as well as television. During the present age of globalisation, American English has extended its range and impact considerably, both worldwide and in the Caribbean. At the same time, individual Caribbean creoles such as Jamaican have also influenced the development of English in North America, by way of diaspora communities, the global success of reggae, dancehall and Rastafarianism, and the use of ‘Cyber-Jamaican’ on the web.