One of Australia's most prolific illustrators, Stackpool was born and grew up on a grazing property in Queensland. In 1939 he won a scholarship to the Queensland Art School but did not finish the course, having chosen to enlist in the army during the Second World War. During the war he was frequently employed in rendering topographical drawings for gun placements. One of his Battery Commanders was George Ferguson (q.v.), whose peace-time occupation with Angus and Robertson launched Stackpool into a career as an illustrator after the war.
Stackpool quickly found a niche in Australia's booming post-war 'pulp fiction' industry. During 1950-1953, Stackpool produced dramatic cover illustrations for the 'Invincible Mysteries' series of British, American and Australian crime novels. He enjoyed even greater success with the Cleveland Publishing Company, where Stackpool painted countless crime and western covers, including most of those used on the 'Larry Kent/I Hate Crime' novels throughout 1956-1971.
Stackpool illustrated approximately 100 children's books. He illustrated some of the Australians in History series, published by Collins during the 1970s. He is quoted in Walter McVitty's book Author & Illustrators of Australian Children's Books (1989) as seeing illustration 'apart from being an art form, as essentially a didactic craft - even when it is ostensibly only to amuse'. He listed the three essentials of illustrating as sound draughtsmanship; accuracy of detail; and good clear technique in rendering, whether in colour or black and white, for good reproduction in the printing.