Harold Freedman was born in Caulfield, Victoria, in 1915. He studied at the Melbourne Technical College from 1929 to 1935, and from 1936 he worked as a freelance illustrator and cartoonist.
During the Second World War Freedman enlisted in the RAAF and was appointed as a war artist attached to the RAAF Historical War Records Section, along with Eric Thake and Max Newton. He worked here from 1944 to 1945, in Borneo, Noemfoor and around Australia.
The Memorial has a large collection of paintings produced by the RAAF artists, which were distributed between RAAF bases and the Memorial after war.
In 1968 the Memorial commissioned Freedman to produce a large mural depicting the history of Australian military aviation. The mural took five years to complete and features every aircraft used by the RAAF up until the Vietnam War. On completion of the mural Freedman was appointed to the unique position of Official State Artist for Victoria, which he held from 1972 to 1983. During this appointment he produced more large-scale murals, including the Cavalcade of transport in the main hall of Spencer Street Station and The History of racing at Flemington Racecourse.