The Archibald Prize is regarded as the most important portraiture prize, and is the most prominent of all arts prizes, in Australia. It began in 1921 after a bequest from J F Archibald, the editor of The Bulletin, and is awarded annually by the Trustees of the Art Gallery of New South Wales for "the best portrait, preferentially of some man or woman distinguished in Art, Letters, Science or Politics, painted by an artist resident in Australasia during the 12 months preceding the date fixed by the Trustees for sending in the pictures."

The Archibald is the only artist's prize that receives much attention in the general press. Part of the reason is probably that many of the paintings feature prominent Australians such as actors, sportspeople, and politicians, and thus making the art more accessible than other genres. Additionally, the prize has historically attracted a good deal of controversy and at least two court cases; the first in 1943 when William Dobell's win was challenged because of claims it was a caricature rather than a painting, and in 2004 when Craig Ruddy's image of David Gulpilil, which won both the main prize and the "People's Choice" award (voted by those who attend the exhibition of the finalists), was challenged on the basis that it was a charcoal sketch rather than a painting.

List of winners

Year - Artist - Title

• 1921 - W B McInnes - Desbrowe Annear
• 1922 - W B McInnes - Professor Harrison Moore
• 1923 - W B McInnes - Portrait of a Lady
• 1924 - W B McInnes - Portrait of Miss Collins
• 1925 - John Longstaff - Portrait of Maurice Moscovitch
• 1926 - W B McInnes - Silk and Lace
• 1927 - George W Lambert - Mrs Murdoch
• 1928 - John Longstaff - Portrait of Dr Alexander Leeper
• 1929 - John Longstaff - W A Holman, KC
• 1930 - W B McInnes - Drum-Major Harry McClelland
• 1931 - John Longstaff - Sir John Sulman
• 1932 - Ernest Buckmaster - Sir William Irvine
• 1933 - Charles Wheeler - Ambrose Pratt
• 1934 - Henry Hanke - Self Portrait
• 1935 - John Longstaff - A B ('Banjo') Paterson
• 1936 - W B McInnes - Dr. Julian Smith
• 1937 - Normand Baker - Self Portrait
• 1938 - Nora Heysen - Mme Elink Schuurman
• 1939 - Max Meldrum - The Hon G J Bell, Speaker of the House of Representatives
• 1940 - Max Meldrum - Dr J Forbes McKenzie
• 1941 - William Dargie - Sir James Elder, KBE
• 1942 - William Dargie - Corporal Jim Gordon, VC
• 1943 - William Dobell - Joshua Smith
• 1944 - Joshua Smith - Hon Sol Rosevear, MHR, Speaker of the House of Representatives
• 1945 - William Dargie - Lt-General The Hon Edmund Herring, KBC, DSO, MC, ED
• 1946 - William Dargie - L C Robson, MC, MA
• 1947 - William Dargie - Sir Marcus Clarke, KBE
• 1948 - William Dobell - Margaret Olley
• 1949 - Arthur Murch - Bonar Dunlop
• 1950 - William Dargie - Sir Leslie McConnan
• 1951 - Ivor Hele - Laurie Thomas
• 1952 - William Dargie - Mr Essington Lewis, CH
• 1953 - Ivor Hele - Sir Henry Simpson Newland, CBE, DSO, MS, FRCS
• 1954 - Ivor Hele - Rt Hon R G Menzies, PC, CH, QC, MP
• 1955 - Ivor Hele - Robert Campbell Esq
• 1956 - William Dargie - Mr Albert Namatjira
• 1957 - Ivor Hele - Self Portrait
• 1958 - William Pidgeon - Mr Ray Walker
• 1959 - William Dobell - Dr Edward MacMahon
• 1960 - Judy Cassab - Stanislaus Rapotec
• 1961 - William Pidgeon - Rabbi Dr I Porush
• 1962 - Louis Kahan - Patrick White
• 1963 - J Carrington Smith - Professor James McAuley
• 1964 - No award
• 1965 - Clifton Pugh - R A Henderson
• 1966 - Jon Molvig - Charles Blackman
• 1967 - Judy Cassab - Margo Lewers
• 1968 - William Pidgeon - Lloyd Rees
• 1969 - Ray Crooke - George Johnston
• 1970 - Eric Smith - Gruzman - Architect
• 1971 - Clifton Pugh - Sir John McEwen
• 1972 - Clifton Pugh - The Hon E G Whitlam
• 1973 - Janet Dawson - Michael Boddy
• 1974 - Sam Fullbrook - Jockey Norman Stephens
• 1975 - Kevin Connor - The Hon Sir Frank Kitto, KBE
• 1976 - Brett Whiteley - Self Portrait in the Studio
• 1977 - Kevin Connor - Robert Klippel
• 1978 - Brett Whiteley - Art, Life and the other thing
• 1979 - Wes Walters - Portrait of Philip Adams
• 1980 - No award
• 1981 - Eric Smith - Rudy Komon
• 1982 - Eric Smith - Peter Sculthorpe
• 1983 - Nigel Thomson - Chandler Coventry
• 1984 - Keith Looby - Max Gillies
• 1985 - Guy Warren - Flugelman with Wingman
• 1986 - Davida Allen - Dr John Arthur McKelvey Shera
• 1987 - William Robinson - Equestrian Self Portrait
• 1988 - Fred Cress - John Beard
• 1989 - Bryan Westwood - Portrait of Elwyn Lynn
• 1990 - Geoffrey Proud - Dorothy Hewett
• 1991/92 - Bryan Westwood - The Prime Minister (Paul Keating)
• 1992/93 - Garry Shead - Tom Thompson
• 1993/94 - Francis Giacco - Homage to John Reichard
• 1995 - William Robinson - Self Portrait with Stunned Mullet
• 1996 - Wendy Sharpe - Self Portrait - as Diana of Erskineville
• 1997 - Nigel Thomson - Barbara Blackman
• 1998 - Lewis Miller - Portrait of Allan Mitelman No 3
• 1999 - Euan MacLeod - Self portrait/head like a hole
• 2000 - Adam Cullen - Portrait of David Wenham
• 2001 - Nicholas Harding - John Bell as King Lear
• 2002 - Cherry Hood - Simon Tedeschi Unplugged
• 2003 - Geoffrey Dwyer - a portrait of Richard Flanagan.
• 2004 - Craig Ruddy - David Gulpilil, two worlds (subject to court challenge as of May 2004).