[2][3][4] In 1962, as a member of The Sheiks, he performed at Palisadoes Airport to greet Princess Margaret on her visit to the island to mark Jamaica's independence.
[7][8] He went on to record with The Abyssinians, Soul Syndicate, Lloyd Parks' Skin Flesh and Bones and We the People Band, The Professionals, Alton Ellis, Ja-Man Allstars and Prince Far I, notably on Cry Tuff Dub Encounter Chapter IV, which versioned tunes from Ras Michael & The Sons Of Negus Revelation album, amongst many others.
[2] In the late 1960s Headley Bennett moved to Canada, returning to Jamaica in 1977, playing in the late 70s on Horace Andy's Tappa Zukie Stars label discomix, If I wasn't a Man, built around a variation on the horns refrain from Sound Dimension's Real Rock rhythm, as well as playing on Mikey Dread's Dread at the Controls releases, also contributing to records by Frankie Paul, Al Campbell, Ossie Hibbert, U Brown, Errol Scorcher and Ernest Wilson.
[5] Throughout the late 70s and early 80s, Bennett was consistently in demand and he worked prolifically, featuring on King Tubby's, Prince Jammy and Scientist produced albums by Hugh Mundell, Sonya Spence, Augustus Pablo, Leonard Dillon, The Gladiators, Barrington Levy and The Chantells.
Whilst the majority of his recordings have been as a session musician, he has released two albums where he is credited as the main artist : in the late 1970s he released an album of instrumental versions of R&B, doo wop compositions and soul music ballads with Ossie Scott, entitled Deadly Headly Bennett Meets The Magnificent Ossie Scott, and then in 1981 he recorded a spiritually conscious roots reggae dub album, 35 Years From Alpha, with producer Adrian Sherwood, Style Scott of The Roots Radics, Creation Rebel, Eskimo Fox ( also a graduate of Alpha School ), Carlton Bubblers Ogilvie, Tony Philips and Bim Sherman, featuring versions of The Abyssinians' Satta Massagana as well as Discomix takes on Dennis Brown's Easy Take it Easy and Bob Andy's Unchained AKA Set Me Free.