Andrew was exposed to Wailers music from birth, as his father was the late Peter Tosh and his mother was Shirley Livingstone, sister of Bunny Wailer. Owing to his father's promotional commitments, he spent his formative years with his grandmother. By his early teens he was living with his father, who taught him the basic elements of singing. His first recording session was held at Sonic Sounds in 1985 with DJ Charlie Chaplin producing, resulting in his debut, "Vanity Love". He also recorded "Lick A Shot" with Jimmy Cliff, but the single was not released until the late 80s. In September 1987 Peter Tosh was gunned down in his home and this motivated Andrew to continue his father's work. He began by singing "Jah Guide" and an emotional "Equal Rights" at his father's funeral service, in Kingston's National Arena. He then recorded with Winston "Niney" Holness The Original Man, which was released in the UK on the Trojan subsidiary Attack. However, the label had become unfashionable in the reggae market and the cover design did little to help the album. At the Peter Tosh tribute concert in the USA, he formed a partnership with Carlton "Santa" Davis, George "Fully" Fullwood, Keith "Sterling" McLeod and Tony Chin, who had previously backed Peter Tosh as Word Sound And Power. The result of the partnership was an album recorded in the USA, Make Place For The Youth, which mainly consisted of original material with the exception of a version of Bob Marley 's "Small Axe". Andrew Tosh was also involved in Bunny Wailer's project to release rediscovered Wailers material, as his voice resembled his father's. In 1994 the Heartbeat label in the USA re-released Original Man, complete with dub versions and a vastly improved cover. In the mid-90s he re-recorded his father's hit, "Legalise It", with the additional line, "President Clinton smoke it".