Called a stranger by his family due to the fact that he did not resemble any of them, Cole has a long lasting career in music that dates back to the early days of ska. His first hit was a song he wrote called “In and Out of the Window” for Eric Monty Morris. The success of this song gave him the opportunity to record his own songs. In 1962, Cole recorded his debut song “ Rough and Tough”, which became an instant hit. He went on to record a duet with singer Millicent “Pasty” Todd called “When I call your Name”, which was also met with great success.

Known to be shy when singing he engaged in a series of duets with Gladstone Anderson and Hortense Ellis. He also worked with the top producers of his time such as Bunny “Striker” Lee, Lee “Scratch“ Perry, and Sonia Pottinger.

In 1971, Cole migrated to England where he toured extensively. In 1973 he moved to Toronto, Canada, where he worked as a machinist at a toy factory and later opened up the first Caribbean record shop.

Cole’s son Squiddly is a drummer for Ziggy Marley and Mutabaruka, carrying on his father’s musical legacy.