Jackson has been a professional musician since the 1960s, and since the late 1970s primarily as a blues singer and harmonica player.
[1] Between 1978 and 1992, he was the lead singer of the well-respected Cameo Blues Band, of Toronto, with whom he continues to perform on occasion.
In 1999, he co-founded the Southside Shuffle, an annual Port Credit-based blues and jazz festival that has grown to feature in excess of one hundred acts over three days.
[4] Having battled cancer since 2021, Jackson is still performing and took part in the 2023 Southside Shuffle with the Downchild Blues Band.
The city of Mississauga which Port Credit is a part of honoured him for his 25 years of organizing the event.