A portrait of a pensive David Wenham peering through the window of a Sydney cafe won the $1500 prize which is judged by the Art Gallery of NSW staff who unpack and hang the Archibald entries.
Perth artist Tessa MacKay's hyperreal portrait of the Lord of the Rings and Lion actor was one of the last finalists unpacked at the gallery but an instant winner in the eyes of head packer Brett Cuthbertson.
"It was on the last day, it took all week to get there but as soon as I saw it I knew it was the one," he told AAP on Thursday.
"The depth, the glass, the reflection, the vase and the look on David's face drew me to it."
MacKay said the piece was different from her usual portraits because it incorporated reflections and a landscape.
"(It's) about capturing David's essence in a city that he loves," the artist told AAP.
"After getting to know David a little bit, I came to realise Sydney is just embedded in who he is.
"He meanders around the city frequently."
Wenham didn't attend Thursday's announcement because he's filming the Netflix series The Letter for the King in the Czech Republic.
In a statement, he said: "Aware of my fondness for sitting, people watching and general daydreaming, Tess had a very clear vision of what the look, feel and purpose of the portrait should be."
Just like the actor it portrays, MacKay's work had a transient life.
It began a year ago in a studio in Fremantle, moved to MacKay's granny flat in Perth before the finishing touches were added at her mother's apartment.
"My mum's apartment is upstairs so to get David in and out of the building, we've had to take all the doors off the balcony and get the work up and over the balcony," she said.
Wenham was the subject of Jordan Richardson's portrait David Wenham and Hat in 2018. He was also the subject of Adam Cullen's Archibald Prize-winning Portrait of David Wenham in 2000.
The $100,000 Archibald Prize will be announced a day before the finalists go on exhibition from May 11. A record 919 entries this year were whittled down to 51 finalists.
