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Sid Barron was born in 1917 in Toronto. His mother had fled England after becoming pregnant to a Belgian soldier billeted with her parents. The two soon moved to Victoria where Sid was adopted by his aunt. He was unaware of his parentage until much later in life.

As a child, Barron compensated for a troubled home life and a speech impediment by taking up drawing. He developed a lifelong fascination with boats, making obsessive scrapbooks of photographs and drawings of shipping. At the age of 21, he met Allan Edwards, who gave him his first formal art lessons (along with Pierre Berton, among others). He painted harbours, ships and beach scenes in watercolour and tempera (he was allergic to oil paints).

Barron earned a living as a commercial artist painting schedule cards for Union Steamships in Vancouver and designing boxes and neon signs. During World War II, he moved to Toronto where he produced war illustrations for the Toronto Star and created original Canadian comic books. In the late 1950s, Barron took up cartooning at the request of the Victoria Daily Times publisher, Stu Keate. His content was topical rather than political, similar to the British cartoonist Giles and Vancouver's Norris.

In 1961 (with an introduction from Pierre Berton) he was hired by the Toronto Star as an alternate to the popular Duncan Macpherson. In 1975, Barron met fellow artist Jesi, in an art therapy session. They married in 1977. They eventually settled in Coombs, British Columbia in 1987 where they ran their own studio/gallery for ten years. After their return to Victoria, Sid and Jesi Barron’s paintings were, for many years, featured at the Gallery in Oak Bay Village.