As a founding member of the Group of Seven A.Y. Jackson was intrinsic to the development of the Canadian art aesthetic.

Eventually working mainly in oil, he received his earliest artistic training in his hometown of Montreal when he went to work for a lithography company at the age of 12.

He began his formal studies in 1902, first working under William Brymner at the Art Association of Montreal, and later at the Chicago Art Institute from 1905 to 1907. Immediately following his education in North America, Jackson traveled to Paris to study under Jean Paul Laurens at the Academie Julian where he was heavily influenced by Impressionism. Subsequent to his studies he traveled and painted in England, France and Italy, and returned to Quebec in 1914.

With their focus on capturing the Canadian landscape, the paintings that Jackson produced upon his return attracted the attention of fellow artists J.E.H. MacDonald and Lawren Harris. They eventually convinced Jackson to move to Toronto, where he shared a studio with Tom Thomson and became involved in all major group trips to Algonquin Park, Georgian Bay, Algoma and the North Shore.

Jackson exhibited with the Group of Seven throughout the 1920s. He also made regular sketching trips to Quebec in the spring, travelled to regions such as the Canadian Arctic in the summer, and returned to the studio in Toronto to paint his canvases.

With a career that remained active into his eighties, Jackson exhibited with the RCA from 1904 to 1957, and with the AAM from 1903 to 1946.