Four months before submitting her Archibald Prize entry, Tessa MacKay, sent the actor David Wenham an image of the work.
A favourite sitter of many artists, including 2000's Archibald Prize winner, Adam Cullen, Wenham's feedback was that she had been too kind to his face - "the judges love wrinkles".
"I spent another two to three months on his face alone . . . . went down another brush size and gave those crevices a bit more life," Mackay recalls.
It did the trick for head packer Brett Cuthbertson who awarded the hyperreal portrait of Wenham in a Newtown cafe titled Through the Looking Glass, this year's Packing Room Prize.
"I love that your eyes are drawn to the pairing of the salt and sugar and the glass vase in the background. That David's in it is a bonus."
The $1500 prize is selected by gallery staff who receive, unpack and hang entries with Cuthbertson commanding 52 per cent of the vote. No Packing Room prizewinner has gone on to win the Archibald Prize but the depth and technical clarity MacKay's work has tongues wagging: Is this the work to break the curse?
MacKay, 27, is mostly self-taught, is unrepresented by a gallery and is a first-time finalist with only her second entry.
The artist met Wenham through her writer-director husband Roderick MacKay who is to direct the actor on his feature film, The Furnace, and she asked him to sit for her in the vault of the Art Gallery of NSW when she was unloading her previous entry, a huge portrait of Australian playwright, Trevor Jamieson.
Filming in Prague, Wenham paid tribute to MacKay's gaze in a statement: "Windows within windows, multiple reflections and numerous light sources added a degree of technical difficultythat was beyond my brain processing capacity."
The prize was a huge deal, MacKay acknowledges, having flown in on Thursday morning from Vietnam to accept the prize."I'm not represented by a gallery. I represent myself which is a bit hard for an emerging artist. Having this sort of exposure is priceless.''
Finalists for the Archibald (portrait), Wynne (landscape or figurative sculpture) and Sulman (genre, subject or mural) prizes and the Young Archie were also unveiled.
The Archibald carries $100,000 prize money for the winning artist with entries to be painted in the past year, from at least one live sitting. The Packing Room Prize reflects popular sentiment but no winner has gone on to win the main prize.
Among the 51 finalists for Australia's oldest and arguably most popular art prize are leading lights of Australian contemporary art, former Archibald Prize winners Euan Macleod, Del Kathryn Barton, and Nigel Milsom.
Like Barton, Vincent Namatjira, Mirra Whale, and Tsering Hannaford were finalists for the second year in a row.
Highly commended last year, Namatjira painted fellow Indigenous artist Tony Albert, renowned for his fascination with kitsch ''Aboriginalia''.
Almost a quarter of the finalists were Archibald newcomers, and most were either self-portraits or of sitters who came from the art world. Imants Tillers painted Greg Inglis while Jun Chen's portrait of Li Cinxin, director of Queensland Ballet, captures "Mao's last dancer" in rehearsals. Vietnamese born artist, comedian, and author Anh Do painted artist, director and a founder of the Yellow House Artist Collective, George Gittoes.
ABC identities and friends Annabel Crabb and Leigh Sales were captured separately by artists Jordan Richardson and Mirra Whale.
Musician Megan Washington was painted by Loribelle Spirovski with baby, while artists Katherine Edney and Natasha Bieniek painted themselves in advanced stages of pregnancy.
- SMH/The Age