Harold Freedman's father Julius was born in Bristol, England, and migrated with his parents at four years old to Australia where they lived in Carlton.
In 1936 he worked as a freelance illustrator and cartoonist for Melbourne weeklies; His ink cartoon Calvalcade of Billy 1940, is in the State Library of Victoria, donated by the artist.
In 1954, while living in Boronia, he was commissioned to produce a painting of the coat of arms of Victoria as the backdrop for the state dinner with Queen Elizabeth II on her visit to Australia.
He and his assistants, artists Joe Attard and David Jack, aided by calligraphist Bruce Walker, commenced The History of Racing in 1984,[6] a series of seven 10 × 6 m murals, completed in time for the Australian Bicentenary.
[7]When Spencer Street Station underwent radical redevelopment (2002–2006) and was renamed Southern Cross, Freedman's History of Transport in Australia above the passenger waiting hall was removed,[8] but due to bargaining by the CFMEU,[3] it remains on display above shop-fronts in the adjacent retail centre, DFO.
[9] The participants, whom he actively recruited and who included Harry Rosengrave, Fred Williams, Charles Blackman, Tate Adams, Barbara Brash, Ian Armstrong, Kenneth Jack, and Leonard French, joined his informally named Melbourne Print Group for which he "acquired" supplies that they were free to use, such as lithography stones, metal plates and ink.
[3] Kenneth Jack acknowledged that; "There is absolutely no doubt that Harold Freedman was responsible for the initiation of a great forward movement in printmaking in Australian art.
at the Australian War Memorial over the first half of 1989, and then touring regional and capital cities, were surveyed by a marketing company, and beside Stella Bowen's Hallifax Crew, William Dobell's Billy Boy, Freedman's Beaufighter Pilot[12] proved to be the most popular.
After his cock-pit was fired upon over Italy, Middleton flew his damaged bomber over the Channel so that his crew could safely bail out close to the English shore.