Dobell won the Archibald Prize, Australia's premier award for portrait artists on three occasions.

In 1931 he moved on to Belgium and Paris, and after 10 years in Europe returned to Australia – taking with him a new Expressionist style of painting as opposed to his earlier naturalistic approach.

[4] In 1944, he had his first solo exhibition including public collection loans at the inauguration of the David Jones Art Gallery, Sydney.

In 1949, he visited New Guinea as a guest of Sir Edward Hallstrom with writers Frank Clune and Colin Simpson.

Between 1960 and 1963 TIME magazine commissioned Dobell to paint four portraits for covers, one per year, of: Sir Robert Menzies, Prime Minister of Australia; South Vietnam's President Ngô Đình Diệm; Frederick G. Donner, the Chairman of General Motors; and Tunku Abdul Rahman, Prime Minister of Malaysia.

In 1964, Dobell exhibited in a major retrospective at the Art Gallery of New South Wales and the first monograph of his work was written by James Gleeson.

This was contested in 1944 by two unsuccessful entrants (Mary Edwell-Burke and Joseph Wolinski),[5] who brought a lawsuit against Dobell and the Gallery's Board of Trustees in the Supreme Court of New South Wales on the grounds that the painting was a caricature and therefore not eligible for the prize.

In November 2023 it was announced that Dobell was one of 14 people, places and events commemorated in the second round of blue plaques sponsored by the Government of New South Wales alongside Kathleen Butler, godmother of Sydney Harbour Bridge; Emma Jane Callaghan, an Aboriginal midwife and activist; Susan Katherina Schardt; journalist Dorothy Drain; writer Charmian Clift; Beryl Mary McLaughlin, one of the first three women to graduate in architecture from the University of Sydney; Grace Emily Munro, Syms Covington; Ioannis (Jack) and Antonios (Tony) Notaras; Ken Thomas of Thomas Nationwide Transport, Bondi Surf Bathers' Life Saving Club and the first release of myxomatosis.