Ryan's portrait of writer Tom Keneally was among 39 finalists for the prestigious Archibald, but he was the only artist also short-listed for the Wynne Prize for landscape painting and the Sulman Prize for best subject painting, genre painting or mural project.

Gallery staff said it was rare for an artist to be a finalist in all three prizes. But it is not the first time for Ryan, who also made the celebrated trifecta in 2006.

The Archibald is notorious for its controversial works, but it is Ryan's Sulman entry - depicting Governor Arthur Phillip and his Aboriginal boyfriend having a "love picnic" - that is likely to create a stir.

"It is fairly controversial, but in Tom Keneally's book, The Commonwealth of Thieves, there was a veiled suggestion that Governor Arthur Phillip was gay, which I thought was wonderful," Ryan said yesterday.

"I am actually not out to shock but I am out to challenge our culture and cultural stereotypes."

The only artist to have won the trifecta was Brett Whiteley in 1978.

Also announced yesterday at the Sydney gallery was the Packing Room Prize, which was won by Paul Jackson's portrait of Paul Livingston's Flacco character.

The winners of the Archibald, Wynne and Sulman prizes will be announced on March 6.