Hewitt is considered one of the top reggae artists in Canada. In addition to being the creator of the "Canadian Reggae Music Awards" in 1985, Winston is the original lead singer and one of the founding members of Jamaica's top international reggae vocal group 'The Pioneers'. Hewitt, working out of Toronto, Canada has taken part in most of the reggae festivals across Canada and around the world. Winston has performed with superstars such as Jimmy Cliff, Bob Marley, Dennis Brown, Marcia Griffiths, Freddie McGregor, Jackie Edwards, Dobby Dobson, Ernie Smith, Millie Jackson, Jerry Butler, The Manhattans, Melba Moore and many others.
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