Springwood native David Darcy's striking portrait of Aboriginal elder Daisy Tjuparntarri Ward won this year's people's choice award at the Archibalds.
It is the second such award for Darcy, who also took out the people's choice in the National Photographic Portrait Prize in 2016 with his photo of actor Levi Miller, taken on location of the sequel to the hit Australian movie, Red Dog.
Darcy's Archibald prize sparked memories for one Katoomba resident.
Michael Minns contacted the Gazette to talk about the work of his great-uncle Benjamin, who painted what is believed to be the first Indigenous portrait ever hung in the Archibald.
It was 1924, three years after the Archibald started, and Minns' work was of David Unaipon, whose image later adorned the $50 note.
Unaipon was an inventor, writer and preacher, as well as the first Aboriginal author to be published.
The archival team at the Art Gallery of NSW said: "We can confirm that it is highly likely that B.E. Minns' 1924 Archibald work was the first portrait of an Aboriginal person hung in the Archibald.
"The painting was catalogue number 19, exhibited 10 January-31 March, 1925, and the artist apparently identified the sitter as David Unaipon to the Gallery at the time.
"We have no other indication that any of the other unidentified earlier portraits in the Archibald was of an Indigenous person."
Michael Minns said he had unearthed the information about his great uncle, his grandfather's brother, while doing family tree research.
B. E. Minns was considered one of the former watercolourists of his time.
He founded the Australian Watercolour Institute and in 1938 he was posthumously awarded the Sydney sesquicentenary prize for a historical oil painting of Captain Cook meeting Aboriginal people.
He was also a prominent black-and-white artist and contributed to The Bulletin magazine for 40 years.
But he was castigated by his peers for concentrating on Indigenous subjects for his work, according to his great nephew.
Michael Minns said he rang Mr Darcy, who has moved from the Mountains to Murrurundi, to congratulate him on his people's choice award.
"I told him my great uncle was the first to have an Indigenous portrait hung in the Archibald," Mr Minns said.
The regional tour of this year's Archibald finalists will not reach Katoomba, as it did in 2015, but it will be in Bathurst in May-June next year.