First comprised of Winston 'Pipe' Matthews on lead vocals, Lloyd 'Bread' McDonald, and George 'Buddy' Haye, the Wailing Souls carried the moniker of the Renegades during the late 1960’s. This line-up recorded backing vocals for an Ernest Ranglin album before breaking up in 1968.

'Pipe' and 'Bread' teamed up with two other singers after that, Oswald Downer and Norman Davis, and they went on to work with Coxsone Dodd's famous Studio One label recording label. They recorded a number of singles there, and were also billed as the Classics, in addition to their Wailing Souls name.

In the early 70's, the Souls recorded for Bob Marley's Tuff Gong label, as Pipe and The Pipers. The group’s vocal power, and song writing ability has kept the group in the spotlight, and in 1974 the group changed again when Downes and Davis left and 'Buddy' Haye rejoined.

The group entered another era of their careers as they began work with famed producer "Jo Jo" Hookim and his Channel One label. The Souls then started their own label in 1977, Massive. In the early 80's the now quartet (with the addition of Rudolph ‘Garth’ Dennis from Black Uhuru fame) worked with a number of hot producers including Sly and Robbie, "Junjo" Lawes' and Linval Thompson.