Harry Reade travelled with his itinerant father during the time of the Great Depression and his schooling was limited to four years of primary education. He began work at the age of thirteen as a foundry labourer and later worked in a range of occupations including fisherman, kangaroo-shooter, wharfie, comedian, cartoonist, printer and book illustrator. His work took him overseas to places such as Moscow (while a journalist) and he was also a seaman in the Danish Merchant Navy.
Reade hopped on a ship in 1959 when the news of Fidel Castro's revolution broke, and arrived in time to fight in the Bay of Pigs (with Castro's force). He stayed in Cuba for ten years, during which time he aided the revolution by fighting and also by producing cartoons for the cause. Later Reade lived on a small yacht in Cairns for some years, and was the subject of the ABC's Australian Story program on the 9th October 1996.