He was born in Montréal, Canada, but also lived in England and France, showing his work in London from 1910 to 1935. He studied at the Conseil des arts et manufactures in Montréal with Edmond Dyonnet. He worked in Chicago from soon after his trip until 1907 and studied at the Art Institute of Chicage under Clute and Richardson. In 1907 he went to Paris and studied at the Académie Julien under Jean Paul Laurens for six months. He also traveled to Rome, Florence and Venice. He fought in the First World War in 1914 but after being injured in 1916, became a war artist the following year. In 1920, after a stay at Georgian Bay, Jackson exhibited in the first Group of Seven exhibition after joining the group. That same year, he was elected a member of the Royal Canadian Academy of Arts.