[7][8] After high school, Watson and fellow Hangman Buzz Thompson organized a band called Cold Porridge with drummer Paul Healey and keyboardist Mike Townes.

[9] Watson worked in a factory job for a short while, and then sang and played lead guitar in a number of short-lived bands in the Peterborough area, including The Outcrowd, Sumac, Bacon Fat, Uncle Bobby’s Aerial ballet.

[5] He lived in Memphis, Tennessee, for many years, playing stage shows and as a studio musician,[11][12] and performing in the house band at the Rum Boogie Tavern.

Along with some additional tracks recorded live with local musicians by James McKenty at the Historic Red Dog Tavern in Peterborough, these were released as the album From the East Side – Bobby Watson.

[22] As of 2019, he continues to perform with various blues and rock groups at events and venues around southern Ontario,[23][24][25] and leads his band, Bobby Watson and the Crown Royals, in a regular Tuesday pub night in Peterborough.