450. Desmond Dekker
Prior to the ascent of Bob Marley, one of the biggest stars on Jamaican soil was that of Desmond Dekker. It is often forgotten that Dekker (and not Marley, nor recent Hall inductee Jimmy Cliff) was the first Jamaican to crack the top ten in England and the United States. As such, he may have been the first voice that many had heard representing the Caribbean and helped launch many record executives to look at that island for talent. The Ska superstar did manage to become a big star in Britain, and had he achieved half of that in America, he would have a better shot to become the third Jamaican representative than he likely has now.