The Jamaican reggae singer known as Winston Groovy was born as Winston Tucker in 1946 in Kingston, Jamaica. Winston recognised his love for music at an early age and began paying attention to the local music scene.

In the 1960's he and his father emigrated to Birmingham, London and he quickly joined a band there called The Ebonites, where he functioned as their lead singer and songwriter. He and the band toured London extensively, even making their their way to France, but they never made any formal recordings. This changed when he moved to London in 1969 where he met Ska legend Laurel Aitken who was eager to record the singer. It was at his point that he changed his name to Winston Groovy. The pair went on to produce hits such as "Island in the Sun", "Free the People", "Funky Chicken" and "Yellow Bird".

Winston then joined Trojan records and began to associate with established artistes such as John Holt, Ken Booth, Bob&Marcia and Desmond Dekker. It was at Trojan that he recorded hits such as "So Easy" and "I'm Going Back". He later met with Eddy Grant and was given the opportunity to record on his label. This resulted in the production of one of his most famous compositions to date, "Please Don't Make Me Cry" which sold close to 60,000 copies. The Band UB40 later covered the song and it became an international hit.

In 1985, Winston moved to Jive Records Label and there recorded a reggae version of the Commodores hit "Night Shift", which went on to become a monster hit all over Europe as the song reached #83 on the UK charts. This spawned another tour of Europe for Winston.Winston eventually set up his own label in 1990 called W.G. Records and he produced 4 albums of his own here.

The association with UB40 did not end with "Please Don't Make Me Cry" as the band invited Winston to record with them in Birmingham. He was featured on the documentary "UB40-Story of Reggae" and was a guest on the band's 2000 Labour of Love 3 tour in London.

While Winston has for the most part stepped away from the music industry, his soulful voice defies time in the 13 albums he managed to record during his time as an active performer.