Charles Waterstreet. Photo by @lilymayers, reposted with permission

The Archibald Prize, Australia's most prestigious art competition, has continued its long tradition of controversy. It is awarded for a portrait ‘preferentially of some man or woman distinguished in art, letters, science or politics, painted by any artist resident in Australasia’.

Both artist, Nigel Milsom, and subject, Charles Waterstreet, have a colourful history in the law. They met and became friends when Milsom was convicted and gaoled for a 2012 armed robbery. Waterstreet was his lawyer. He is best known as co-creator of the television series Rake, whose main character Cleaver Greene is loosely based on his life and career. His proud re-tweet made the connection:

His Rake'ness as painted by Nigel Milsom is not only magnificent it deservedly won the Archibald! @CCWaterstreet https://t.co/i4tcpt4tMX

— missdlight keri (@missdlight) July 17, 2015

In fact, at times it seemed like Charles had won the award:

I interviewed the charming Charles Waterstreet today #archibald2015 pic.twitter.com/xDAiBOBiFZ

— lily mayers (@lilymayers) July 17, 2015

Not all art lovers appreciated the many media headlines that focused on Milsom's criminal record:

So sad the media is focussing on this years #archibald2015 winner in a negative light. He did his time, now let's celebrate his prize.

— Lila A (@lila_afiouni) July 17, 2015

No room for redemption on the news wires “Former armed robber wins Archibald Prize” (ABC News 24) #archibald2015 #ArchibaldPrize #art

— Alasdair Macintyre (@aecap) July 17, 2015

But others on Twitter had no qualms about raising his criminal past:

Who says crime doesn't pay? Nigel Milsom wins #archibald2015 #archibaldprize

— James Powditch (@james_powditch) July 17, 2015

There were the inevitable online art critics. It is a recurring theme of the Archibald that the winner is a poor choice:

Seriously? $100,000 prize for this? Seriously? #archibald2015 #imustbeatotalphilistine http://t.co/bBVjdJ4Yhq

— Tim Meade (@PompeyPom) July 17, 2015

This tweet referenced the famous winning entry by William Dobell in 1943, which faced an unsuccessful legal challenge that argued it was a caricature not a portrait.

Archibald winner is just a Francis Bacon , Bill Dobell rip off … Once again , art loses …

— george Barnes (@georgebarnes311) July 17, 2015

Raichel laid out the similarities for all to see:

@ArtGalleryofNSW #Dobell, Milsom, Dobell, Milson, Dobsom?…#archibald #Waterstreet #portraitprize pic.twitter.com/ZO3ebMg8HP

— Raichel (@DanteInExile) July 17, 2015

Joanna Mendelssohn was very positive at The Conversation arguing that it is “our ‘most fun’ festival of faces”. She explained:

First, the Archibald is – in essence – not an art prize but a celebration of the personalities who define Australia, and especially Sydney. Waterstreet, the flamboyant inspiration for the ABC television series Rake, has to be a front runner on those grounds alone.

In addition, Milsom was the winner of the 2013 Moran Prize – and a convicted criminal – all of which makes good copy. The Archibald is, above all things, about media coverage.

A thread running through much of the discussion of Australian literary and art prizes is the lack of gender balance. This has been a contentious point with the Archibald, regarding both artists and their subjects. There were many tweets linking to the Sydney Morning Herald newspaper article Archibald Prize 2015: It takes balls to be a winner:

Archibald Prize 2015: It takes balls to be a winner# http://t.co/YDfegJE8m1 pic.twitter.com/KECIedAU6F

— Gi Ma (@gima2327) July 17, 2015

Finally, Peter Pidgeon shared a popular video post by the Australian Broadcasting Corporation, which contains a famous relation of his:

Wep's 3 wins: 1958, 1961 & 1968; images #37, #40 & #46 – The changing face of the Archibald: 1921-2015… http://t.co/r2D7T3IvLq

— Peter Pidgeon (@Pidgeoncoop) July 18, 2015

It gives a chance to judge the worthiness of the winners for yourself.