Tosh was exposed to the music of his father's group The Wailers from an early age, his mother, Shirley Livingstone, also being the sister of Bunny Wailer. His first recording session was in 1985, produced by Charlie Chaplin, and resulting in the single "Vanity Love". After his father was shot dead in 1987, he performed two songs at his funeral, "Jah Guide" and "Equal Rights".

He moved on to work with producer Winston Holness on his debut album, Original Man. This was followed in 1989 by a second album, Make Place For The Youth, which was recorded in the United States and was nominated for a Grammy Award for Best Reggae Album.

He toured with The Wailers Band in 1991.

In 2004, he recorded an album of songs by his father, Andrew Sings Tosh: He Never Died.

In 2007, he announced that he was working on his fourth studio album, Focus.

In 2011, he announced that he was working on a new album, named "Eye to Eye", featuring Kymani Marley, expecting an August 2011 release date.