Born in Kingston Jamaica on the 25th May, Winston was destined to be a consummate performer, a singer of extraordinary talent. From the earliest days Winston was singing as a choir boy in the local Roman Catholic church, but his ability to bend his body like a contortionist earned him a place in a local touring company Bim and Bam. The show known as 'Healing in the Bamyard' travelled around the Island and even though he was only just seven years old, Winston would after school and at weekends travel with the company to the theatres to perform. His part as the snake in the show earned him the nickname Cobra Boy and he continued to perform with the company for several years until he was eleven. Winston then won a place in the Vere John talent shows, known as 'Opportunity Hour'. Staged over many rounds, the audience was often wild, throwing rotten fruit and booing at those artists that didn't make the grade. While that never happened to Winston, those shows provided a great grounding for his future and by the time Winston was thirteen he had won the final twice. He was then sent to the USA to live with Uncle and Aunt in Miami and did not return to Jamaica for two years. Upon his return to Jamaica it was not long before he had teamed up with Edwin 'Bammo' Brown to form the Sheridans a four piece vocal group with Owen 'Spirry' Roberts and Pat Kelly). Although Winston had started an apprentaship as a printer, the Sheridans managed to enter the 'Star is Born' competition and came second. This lead to a number of gigs and the group ended up supporting Carlos Malcolm, a top band at the time. They toured through the USA and Canada for nearly two years, before the Sheridans eventually broke up. Working the cruise ships as a singer, Winston earned his passage back to the USA. It was while on one such trip that a friend Bob Davies introduced Winston to the Jazz pianist Chuck Bird. Chuck was so impressed with Winstons' voice that he took him under his wing, providing him with 'voice culture' lessons and introduced Winston to Bernard Burlett who became his mentor and support while in the USA. But it was Chuck who managed to get Winston his first solo break. Buddy Grecko was fronting the Jackie Gleeson Orchestra at the prestigious Fountain Blue Hotel who were playing hosts to a special event with Spirew Agnew as guest of honour. Buddy developed laryngitis and Chuck Bird got Winston to fill in. That show spurned many more until Winston returned to Jamaica in 1968, where he met his old school friend Jackie Estick who introduced Winston to Coxone Dodd of the famed Studio One. It was there that he recorded over twenty tracks of which 'California Dreamin' and 'Mr Fixit' became two big hits for Winston in just two years. In 1969 he recorded 'Go find yourself a fool' for the Treasure Isle Label.

The song was written by Bruce Ruffin, a member of the 'Techniques' who backed the song in the original recording. The same day that the track was recorded Winston flew back to Miami to do some shows and by the time he returned to Jamaica a few weeks later the song California Dreaming was hitting in England. Winston jetted strait into London, tying up with Junior Lincoln of the Bamboo label who had released the track in the UK. Tony Blackburn had made California Dreaming his 'hit pick of the week' on Radio One but when Winston arrived in the country, Tony made it again his hit pick of the week and so the song ran for two weeks, played every day. That was the one time that Tony ever made a track run for two weeks. Junior took Winston to a nightclub at the Cumberland hotel where he was fortunate enough to be introduced to Dick Katz who was to become Winston's Manager and agent for many years. Dick introduced Winston to the Bailey Circuit, which was a tour of prestigious clubs and venues. Winston went back to Jamaica until 1971 and returned to the Bailey Circuit and tour England. It was a great time and Winston met Angie, who he fell in love with at first sight. He asked Angie to marry him and she refused. Winston drank and smoked too much. So Winston stopped drinking and smoking and they were married within the year. To tour England on the Bailey circuit was a prestigious event in those days, even more so for a Jamaican artist at that time. Winston stayed on the circuit for four years, playing night after night, but was getting itchy to get back into the studio and start doing some Reggae again. He met up with Stanley Pembleton who had also met Dave Barker from the duo 'Dave and Ansel Collins' and they started working with the Manfred Man studio.

Winston was recording again and put down the soul track 'Extra Careful' which in 1975 they got a deal for, with MCA. Although MCA worked with Power Exchange the label and Production Company, they provided the finance for Stanley and Winston to start their own production company, Workhouse Productions.

Stanley and Winston sent to Jamaica for Alton Ellis, Ken Parker and Slim Smith. The guys came over and the company put them up in Jessmund Avenue in Wembley where they lived with Bobsy, who now days has a pressing plant in Park Royal. They recorded about eight songs during that period. With Dave Barker and Bobby Davies, Winston started the group the Connections and recorded a couple of new tracks. The facilities that they had were excellent, the engineer was Phillip Chen (who went on to play bass for Rod Stewart) as well as some of the best musicians around at the time. Extra Careful did very well for them, sounding like an American track. Winston changed his name to Billy Cole for the track and to this day is known by that name for many people. The Connections toured through 1976-77 trading on the success of Extra Careful.

Through Angie, Winston was introduced to Sid Sargent and then Bill Farley of EMI. Bill and Winston clicked, introducing Winston to Dennis Bovell from Matoumbi. Working together, writing tracks for EMI and mixing for Danny Ray on Trojan, Winston was experimenting with sound. Tracks such as Jump the Gun, Little Green Apples and Don't take my Teeth from Me. But as this started to tire in the late 70's, Winston teamed up with Eugene Thompson, Mel Nixon, and TC Anderson to form Cosmic High. They toured successfully, but more of Winston's time was being taken up with youth work, until in 1980 Winston went back to Jamaica to look after his mother who had become ill. He stayed for eight months until her death in May 1981. Returning to England and his family he again met up with Eugene and Cosmic High continued to tour until 1985. But the band had been together for several years by then and the original energy the group had started to wane.

By chance, he took Errol Brown from the Chosen Few, to the rehearsals for a new show, Black Heroes showing at the Astoria Theatre in London. Winston was blown away by the show but didn't stay to the finish, -Angie wasn't there. So the next day he returned with Angie to come and see the whole show. When he got to the box office he met Flip Frazer the director.

Flip said " I've been looking for you, everybody's been talking about you, come round to the back in the intermission". By the end of the evening Winston had been pulled into the cast and he stayed with the company for nearly five years, touring England and the USA twice. Just before the second tour of the States, Dennis Bovell called Winston and asked him to come down to Matoumbi's studio in Brixton to do some recording for a Frenchman, Philip', who was putting down some tracks for BMG. They spent a great afternoon recording two tracks, 'Stand by Me' and 'Chain Gang'.

So Winston went off to the States on tour with Black Heroes, but when he got back to England, the French had been calling. Stand by me was a hit in France and had sold over 90'000 copies. The song was released as King Cool and 'Stand by Me' ran and ran. From that, BMG asked Winston to record the album His Majesty Requests, which went on to be a huge success in France. After a tour of Japan with B.B. Seaton and another tour with Black Heroes, Clive Davison asked Winston to come and do an album with the Paragons of Beatles and Bob Dylan tracks. So they did the album in 1998. That same year UB40 covered 'Mr Fix it' and Winston did a series of brilliant shows with the band at Wembley Arena.

Winston has been constantly busy in the last few years, teaming up with his old friend A.J.Franklin, working the Chosen Few back together. In 2001 Winton and A.J worked together on an album with Terry Devine-King. The 'Francis and Franklin' album was finished this summer. The dream team collaboration included the famed Lindell Lewis with musicians Horseman, Steel and Broadfinger. Winston has dates in London and Europe now and is going to Jamaica for Heineken Star time this autumn. With singles from Francis and Franklin hitting now and the new album due out March next year, Winston is busier today than he has ever been.