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Gleeson was born in the Sydney district of Hornsby and he attended East Sydney Technical College. As a young man, he was attracted to work of the likes of Salvador Dalí, Giorgio de Chirico and Max Ernst. In 1938 he studied at Sydney Teachers College, where he gained two years training in general primary school teaching. He also joined the Sydney Branch of the assertively experimental Contemporary Art Society. At this time Gleeson became interested in the writings of psychologists such as Sigmund Freud and Carl Jung, which would become major intellectual influences for his art.
During the 1950s and '60s he moved to a more symbolic perspective, notions of human perfectibility. At this time he increasingly fashioned small psychedelic compositions made using the surrealist technique of decalcomania in the background, to suggest a landscape, and finished by adding a fastidiously painted male nude in the foreground. Many of his paintings had homoerotic undertones, something which reflected on Gleeson's own homosexuality. The ideas for these compositions also saw Gleeson move into collage with his Locus Solus series, where he produced a substantial body of work by placing dismembered photographs, magazine illustrations, diagrams and lines of visionary poetry against abstract pools of ink.
Since the 1970s Gleeson generally made large scale paintings in keeping with the surrealist Inscape genre. The works outwardly resemble rocky seascapes, although in detail the coastline's geological features are found to be made of giant molluscs and threatening crustaceans. In keeping with the Freudian principles of surrealism these grotesque, nightmarish compositions symbolise the inner workings of the human mind. Called 'Psychoscapes' by the artist, they show liquid, solid and air coming together and directly allude to the interface between the conscious, subconscious and unconscious mind. Gleeson's later works incorporate the human form less and less in its entirety. The human form was then represented in his landscapes by suggestions, an arm, a hand or merely an eye.
His retrospective in 2004-2005, Beyond the Screen of Sight, included 120 paintings and was exhibited in Melbourne and Canberra. In 2003 the Art Gallery of New South Wales exhibited Gleeson's drawings for paintings.
In September 2007, the largest collection of Australian surrealism ever collected was donated to the National Gallery of Australia by Ray Wilson. The collection included various works by James Gleeson.
- Ani Lamont (22 October 2008). "Father of Australian Surrealism dies". Sydney Star Observer.
- "Gallery gift promises a surreal experience", The Age, 28 September 2007, p.3
- Dunning, Craig (20 October 2008). "Surrealist James Gleeson dies". The Daily Telegraph (Australia).
- "Surrealist painter James Gleeson dies". ABC News. Retrieved 2008-10-20.
- Allen, Christopher (21 October 2008). "James Gleeeson: surrealist, critic and charming pessimist". The Australian. Retrieved 2008-10-24.
- Grandi Artisi - James Gleeson - collection of his paintings
- Eva Breuer Art Dealer - more of his paintings
- James Gleeson artworks (for sale) on art.net.au
- James Timothy Gleeson at Australian Art
- James Gleeson passes away, 20 October 2008, The Daily Telegraph, Sydney, Australia
- Kathy Marks, James Gleeson: Surrealist painter, art critic and curator who drew dark inspiration from contemporary events (Obituary), The Independent, 29 October 2008