JO-JO Bennett left the Military Band to perform on Jamaica's North Coast but was courted by the island's leading orchestra Byron Lee & The Dragonnaires and he recorded several albums with them before choosing to stay in Canada after the groups impressive show at Expo 67.

Once settled in Toronto, JO-JO organized his first Canadian performing group called "The Fugitives" whose home base was the West Indian Federation Club in Toronto. In the seventies and eighties Bennett was involved in many musical venture in Canada (Toronto) and was the prime mover behind the establishment of the first (and only) Black controlled music school.

At this time instructions in the Reggae music genre was introduced under his tutelage. In 1970 while on hiatus in his homeland Jamaica, Bennett released his first and only album "Groovey Joe" while performing live and doing studio work for numerous record companies.