Now in its 94th year, The Archibald Prize is undoubtedly the biggest highlight of the Australian art calendar – it might not always present Australia’s best works, but it certainly delivers those that are the most-talked about. 
A haunting, affecting and, frankly, frightening AF portrait of prominent Australian barrister, SMH columnist, filmmaker and author Charles Waterstreet took out the prestigious gong at an award ceremony held at the Art Gallery Of New South Wales this afternoon. The portrait’s artist, Nigel Milsom, was awarded the $100,000 prize. 
Milsom is now firmly positioned in Australia’s art elite – with his Archibald win today, Milsom has now taken home the highest and second-highest paid art prizes in the country—following on from his 2013 win of the exclusive Doug Moran Prize, attracting a $150K prize for his equally dark portrait ‘Uncle Paddy’
Milsom attracted media attention in 2013 with his Doug Moran Prize win, when he was unable to receive the honour himself – as he was serving a six-year prison sentence for an armed robbery in Glebe
The artist struck a relationship with Waterstreet while the barrister represented him during Milsom’s trial. The portrait reportedly took three years to complete; its resulting passing resemblance to Billy The Puppet from Saw [IMHO] was thus derived from Waterstreet’s “demons” and “complex” character, according to Milsom. 

“Charlie is a very complex person. He isn’t just a law man. He’s a writer, a social environmentalist and is involved in film, photography and theatre too. Despite personal struggles with his own demons over the years, he has managed to dedicate most of his time to the welfare of others.
My portrait is an attempt to depict him as a giant: part-man, part-mythical creature with hands that appear otherworldly, as though the anatomy of his hands has been designed to grasp unnatural disasters, naturally.”

Milsom said Waterstreet, who is the loose basis of ABC TV’s Rake, restored his “faith in the legal system“.

Other highlights of this year’s finalists include:
Filippa Buttitta‘s stunningly executed portrait of legendary two-time Archibald prize winner Judy Cassab:

An incredibly delicate portrait of musician Daniel Johns, by Julian Meagher:

The Prize’s runner-up by Mitch Cairns – an extremely Archibald-y portrait of artist Peter Powditch:

And, tbh, Stewart Macfarlane’s Cory Bernardi, presented without comment:

The Archibald Prize is showing at the Art Gallery Of NSW from July 18 – 27 September 2015.