Each year, Iranian asylum seeker Mahdi Jafarian works through a list of celebrities.
"I have sent letters to Nicole Kidman, Russell Crowe, Rebel Wilson," he said. "The first person who replies to me, I choose them."
Australia's pre-eminent portraiture competition requires that entries depict a "distinguished" subject, who must participate in a live sitting with the artist.
"The Archibald has been my motivation for three years," Mr Jafarian said. "I haven't got into the finals yet. It's not easy, but it's fun."
Previously, the Hamilton South resident has entered portraits of artist Richard Tipping and Newcastle Herald cartoonist Peter Lewis.
"I love art because I think real, genuine art helps you forget all your pain," Mr Jafarian said.
The 34-year-old was once an architecture student at the University of Newcastle, but in 2013 he returned to Newcastle in very different circumstances.
"I had two subjects to finish, but my mother was very sick so I left Australia in 2011," Mr Jafarian said. "Iran's economy collapsed. I couldn't afford to come back."
During this period, Mr Jafarian says he "got into some trouble" with the Iranian government and fled the country, fearing for his safety.
He initially aimed for Finland, but was detained and beaten by Russian police before reaching the country's border. Within 40 days of leaving Iran, however, he managed to get to Jakarta by "foot and plane", where he boarded a boat to Christmas Island.
The vessel and its 90 passengers were rescued by the Australian Navy from sinking during a storm overnight.
"I took them 11 hours to find us. It was a miracle," Mr Jafarian said.
He spent two months in Australian detention centres and, upon his release in September, 2013, returned to Newcastle.
He has remained in the city on a bridging visa, and works as an oven cleaner. He dreams of becoming a barber, which he said "is like sculpture".
In the lead up to the 2019 Archibald, it was five-time Walkley Award-winning journalist Steve Pennells who first answered Mr Jafarian's letters. The pair met for three sittings in Sydney to complete the oil painting.
"I have done a lot of work with asylum seekers and refugees. Usually I'm the one who tells their story," Mr Pennells said.
"So it was pretty humbling to meet someone who wanted to tell mine.
While the portrait didn't make the cut, Mr Jafarian said he was grateful for the opportunity to meet a "real gentleman".
"I loved his smile, that's why I chose to paint it."