Growing up in Kingston Jamaica, Winston listened to all types of music. This helped him develop the ability to sing in eight different octaves to all types of crowds. While living in Jamaica he sang amongst many of the top sound systems such as Stone Love, Inner City, Jam Rock and Exodus. Plus Winston performed with artists such as Ninja Man, Shabba, Cocoa Tea, Thriller U, Wayne Wonder, and Papa San, whom he recorded the song "Me Me Me" with. After moving to Canada in 1990 to further his career he put out his first solo single "Inside of You" on his own label "Indeka Productions" in 1994. This became a big hit in Canada and Jamaica. After the success of his first production Winston put out his album titled "URD1" in 1995. With the album out Winston received many calls for shows. Including performances with Ken Booth in 1999, The Manhattans in 2001, John Holt and George Nooks in 2002. Toronto's Jamaica Day event in July 2002 was three the hard way with Winston Paddy, Wayne Wonder and Professor Nuts. In 2004 the Lyricist Lounge in Toronto was another venue where Winston performed showing his great talent. Since then Winston has put out singles such as the remake of "Sorry 2004", "You, Me and She", "Best Friend" and "He's A Talker". More recent work Winston has done is "Don't Move A Muscle" and his new single "Thin LIne between Love and Hate" which is taking the world by storm.