Cole was born in Kingston, Jamaica in 1945 and nicknamed "Stranger" by his family, as they considered that he didn't resemble any member of his kin. Cole was initially successful as a songwriter, writing "In and out the Window", which was a hit for Eric "Monty" Morris. This success gave him the chance to make his recording debut in 1962, instantly finding success with singles such as "Rough and Tough" and "When You Call My Name" (a duet with Patsy Todd) for producer Arthur "Duke" Reid. Further success followed with singles for Reid through to the mid-1960s, and he also worked with other producers at this time, including Clement "Coxsone" Dodd (a duet with Ken Boothe on "Worlds Fair"), and Prince Buster. Further duets included recordings with Gladstone Anderson (on "Just Like a River") and Hortense Ellis, the tendency to record duets apparently due to his shyness when it came to singing alone. In the late 1960s and early 1970s he recorded with several producers, including Bunny Lee, Lee "Scratch" Perry, and Sonia Pottinger. These included further material with Todd as Stranger & Patsy. In 1971 he emigrated to England, where he toured extensively, and moved on again to Canada in 1973, settling in Toronto. He worked as a machinist in the Tonka Toy factory in Toronto and later opened the first Caribbean record shop in Toronto His first album, "Foward" in the Land of Sunshine, was released in 1976, with a handful of further albums released over the next ten years, most on his own label. In 2006, Cole released his first album in twenty years, Morning Train, a collaboration with Jah Shaka. Cole is featured in the 2009 documentary Rocksteady: The Roots of Reggae, in which he and other stars of the rocksteady era reunited to record a new album of the same name, released in August 2009.