A graduate of the Alpha Boys’ School, Bennett was an established session musician at the time.Throughout the 1960s, he played on some of the biggest songs from the ska and Rocksteady eras.
The solo on one of those songs, Delroy Wilson’s Dancing Mood, is arguably the most memorable interludes in Jamaican popular music; it is Headley Bennett’s signature piece.
Bennett played on hit songs by Don Drummond, John Holt and the Heptones before immigrating to Canada in the late 1960s. On his return to Jamaica in the 1970s, he showed he had lost none of his touch, teaming with the hot Roots Radics Band on big hits by Gregory Isaacs and Bunny Wailer.
It was during their rocking sessions of the 1970s and 1980s that the Radics dubbed the veteran hornsman ‘Deadly’ Headley.
Headley Bennett is now 80 years old and an elder statesman of Jamaican music. In 2005, he was awarded the Order of Distinction by the government of Jamaica for his contribution to Jamaican music.