Keith Anderson was born in Kingston, where his mother worked at Up-Park Camp. At the age of 7 he moved to live with his grandmother in Westmoreland. After his grandmother died, his mother gave him away, and he was subject to beatings at the hands of his adoptive parents.
After several years he returned to Kingston to help look after one of his siblings, but to escape beatings from his mother tried to get a place at Maxfield Park children's home by telling them that his mother had died. They both ended up in court, where he was made a ward of the state and returned to Maxfield Park. At the home, he taught himself to play piano, and began singing in the Kingston Parish Church choir. In the local scout troop he met Tyrone Evans, with whom he formed the Binders.
Bob Andy was one of the founding members of The Paragons, along with Tyrone Evans and Howard Barrett, with John Holt later joining briefly before being replaced by Vic Taylor. Andy left after Holt rejoined and worked for Studio One delivering records and songwriting before embarking on a solo career.
His first solo hit record in 1967, "I've Got to Go Back Home", was followed by "Desperate Lover", "Feeling Soul", "Unchained", and "Too Experienced". He also composed songs for other reggae artists, including "I Don't Want to See You Cry" for Ken Boothe, and "Feel Like Jumping", "Truly", and "Melody Life" for Marcia Griffiths.
He had several hits in the late 1960s, including "Going Home", "Unchained", "Feeling Soul", "My Time", "The Ghetto Stays in the Mind", and "Feel the Feeling". Some of these, and his 1992 hit, "Fire Burning", have come to be regarded as reggae standards and several have been covered several times by other artists.
In the early 1970s, he recorded with Marcia Griffiths as Bob and Marcia, initially for Studio One, but later under producer "Harry J" Johnson's tutelage. They had a major UK hit with "Young, Gifted and Black" (with orchestral backing added for the UK market) and spent time in the UK promoting it, but frustrated by not receiving financial reward from the hit (while producer Harry J had built a new studio and bought a new car), he returned to Jamaica. He continued without Johnson's involvement and returned to the UK where he recorded "Pied Piper" with Griffiths and they toured again. "Pied Piper" gave them another top 20 hit, but the duo was dissolved when Griffiths joined the I Threes.
Disillusioned with the industry, in 1978 Andy put his music career on hold and after taking up creative dancing with the National Dance Theatre Company, concentrated on his career as an actor, starring in the films Children of Babylon in 1980, and The Mighty Quinn (1989).
Andy toured Africa for the first time in 2005, performing at the Bob Marley 60th birthday concert in Addis Ababa, and while in Ethiopia also sang at the President's Palace and gave benefit concerts for the Twelve Tribes organization at the Rastafari movement settlement at Shashamane.
In March 2015 Andy was mugged on Mona Road in St. Andrew and robbed of JA$50,000 and two cellphones, the assailant slashing his left arm with a knife in the attack.