Tim Storrier has received a gift and a curse in this year's Archibald Prize.
On Thursday, the 54 finalists of the Archibald were announced, along with the winner of the Packing Room Prize.
In 23 years of its award, the Archibald Prize has never been won by the Packing Room Prize winner.
"It's a bit of a curse but there's no rule that says it can't happen," Mr Storrier said.
"The Packing Room Prize is decided by Steve Peters and the packing crew, and they see a lot of art but they aren't artists.
"The Packing Room Prize tends to represent the average Australian viewpoint."
The Bowral resident submitted a portrait of Australian comedian Barry Humphries in character as Sir Les Patterson.
"The character's well known so it was greeted with quite an amount of enthusiasm," he said.
The portrait has been two years in the making as Mr Storrier said Mr Humphries was tough to pin down.
"I've known Barry for a long time," Mr Storrier said.
"I wanted to paint the character itself, not Barry.
"It's a very different face to Barry's in a way because he wears grotesque false teeth."
Reflecting on the Packing Room Prize curse, Mr Storrier said you never knew how it was going to go.
"I have no idea who's going to win - it's too difficult to call," he said.
"There's quite a lot of great paintings in the exhibitions."
"If you haven't gotten a phone call by 10 past nine, you may as well stay in bed," Mr Storrier said.
Mr Peters said the standard of entries had improved this year.
"You get the so-so's every year," he said.
"Absolutely hopeless and the shockers. But this year is quite good."
In its 23-year history, the winner of the Packing Room Prize has never won the Archibald, which is judged by the 11 trustees of the Art Gallery of NSW.
But the president of the gallery's board of trustees, Guido Belgiorno-Nettis, described Mr Storrier's portrait as "brilliant" and "funny".
"As soon as it came in the room, we thought this has got to be hung," Mr Belgiorno-Nettis said.
He added: "I loved the Sir Les because it just says so much about our culture … and it's so well-executed."
Brandishing a copy of Sir Les's 1985 book The Traveller's Tool, Mr Storrier read a statement from Sir Les, which typified his politically incorrect brand of humour.
"Thanks to that clever bastard Tim Storrier and his brushwork, generations of young Australian art lovers, in particular nubile members of the opposite sex community will look up to what I have to offer and with any luck, like the eyes of the Mona Lisa, it will follow them all around the room. God bless Australia."
This year, the gallery's trustees chose a higher-than-normal 54 finalists from 884 Archibald Prize entries.
Other finalists include Alan Jones's portrait of Adam Goodes, Sophie Hewson's depiction of herself kissing Missy Higgins and Tim Maguire's double portrait of Cate Blanchett.
Asked to nominate his favourite entries, Mr Belgiorno-Nettis said: "There are lots but if I were to say that, I'd be giving away a potential winner, wouldn't I?"
But he said another portrait of Humphries, Well Dressed For A Sydney Audience, by Rodney Pople "resonated a lot" with him.
He also praised Fiona Lowry's work: "I also liked the very intense portrait of Penelope Seidler, who I know very well. That steeliness in her is there." with the SMH