Benson studied in Melbourne, and was employed by the Sporting and Dramatic News and Melbourne Punch as an illustrator and cartoonist. He also worked for the Bulletin in Sydney. In 1914 Benson enlisted and served at Gallipoli and in France, and was appointed as an official war artist. Following the war he furthered his art studies in London and returned to Melbourne in 1919. Benson was commissioned to decorate the ceiling beams of Winthrop Hall at the University of Western Australia, and he used Aboriginal motifs and earthy colours to do so. He worked on murals in Perth in the 1930s and was known for his caricatures and cartoons of prominent Perth people. Benson was also an art critic for the West Australian and contributed to a number of journals.