How to win the Archibald Portrait Prize


Dear lovely person reading this now,

I need YOUR help today. Yes, you. The one with the dreamy eyes reading this…(here’s a clue: we might change a small part of history together).

Here’s why. The Archibald prize is the most famous art award in the Australian art world. But it’s ways are mysterious. Like a furious tempest that dances to its own tune, who wins the Archibald prize and how they win is a maze surrounded by a labyrinth within a giant puzzle.  Or is it?

Today I embark on a 2 month journey (with my long time collaborator, fellow artist Grant Burrow) to find out how to win the Archibald Portrait Prize. With each tick of the watch face (or sundial if that’s your thing) YOU and I are a moment closer to June 26.

But why is it such a mystery? With so many choices to make (think style, subject, colours, size, medium and approach) it’s daunting, which is why I need your help.

Over coming days you’re going to help me decide each step of the way (like a fly on the wall or HG Wells’ invisible man) the sort of painting I will create and why.

But to start, let’s take a closer look at the interesting history of the Archibald Prize.

The award started in 1921 for the best portrait ‘...preferentially of some man or woman distinguished in art, letters, science or politics, painted by any artist resident in Australasia during the 12 months preceding...' and quickly became coveted by artists not only for the money but the exposure it could bring. In its early years the winners were characterised by realistic portraits in brown tones of prominent social figures. All very staid and predictable of course, until William Dobell in 1943 won by painting a caricature of fellow artist Joshua Smith - a rebellious departure.

Through the controversy William defended himself by explaining he was ‘trying to create something, instead of copying something’.

That might have been an epoch as artists continued to push conventional boundaries right to this day where expression of the subject’s ‘inner self’ is foremost.

But why why does it pickpocket the key to the public’s imagination each year? Famous people or controversy maybe. But maybe you have a different idea?

In the next few days YOU and I have some choices to make together.  In the meantime I have a small favour.  I would be so grateful it you shared this link your most loved friends, family, Prime Minister / President or billionaire moguls.  You can also stay in the loop of my adventure by subscribing to my Newsletter below.

Next I’ll talk to you about the 6 choices we have to make. Stay tuned.

The complete series 'How to win the Archibald Prize'
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Frequently Asked Questions
What Others Are Asking...

These are the most common questions asked of Oscar.


Why are your products so special?

Many products (including wall art and t-shirts) are made by combining stock art (you know, images you can buy on used on bad advertisements) to make pretty patterns that don't mean a lot.

Oscar’s works are original and interesting - all designed and crafted using his own hands onto real paper with his imagination, real pencils and ink. That’s what makes each piece like nothing else in the world.

What are the prints made of? Why are they such quality?

Each piece is printed onto the finest museum grade paper. Oscar chooses the Hahnemuhle brand because it feels and looks superb (if you’re interested it’s acid free and calcium carbonate buffered) plus it can last longer than 100 years!

The inking process is called giclée printing and is a high-quality way of getting ink onto the best paper.

id="size" Which size is right for me? A few helpful things to consider:

A4 is small and good for a small desk, kitchen or small wall like a corner.

A3 is medium and good for a larger desk, larger kitchen or moderate sized wall.

A2 a larger and really nice on a wall, behind a bed or desk, adorning a hallway or thoroughfare.

A1 a very large and a wonderful way to make an impact in a room, office, reception, thoroughfare or atrium. Pow.


A4 210 x 297 mm | 8.3 x 11.7 in
A3 297 x 420 mm | 11.7 x 16.5 in
A2 420 x 594 mm | 16.5 x 23.4 in
A1 594 x 841 mm | 23.4 x 33.1 in


Do you offer free worldwide shipping?

Oscar offers free shipping to anywhere in the world. The farthest flung so far is the Netherlands, United States and England but he’d love to go even further! (perhaps you’re from Nepal or Antarctica maybe?)

How can Oscar offer free shipping?

Well, Oscar loves free shipping and it’s worth what it costs him for radically happy customers!

Can I return and get a refund if I’m not 100% happy?

Yes! Of course. Oscar wants you to be radically happy and satisfied (that’s good business isn’t it? But also good humanness...). We’re convinced you will be! But if for whatever reason you’re not super happy please contact us and we’ll arrange a full refund as soon as humanly possible.


Oscar is Award-Winning?

Yes. He’s entered and won art prizes including for a piece about a magical bus and its passengers and a 22 page piece Moleskin about a boy who woke up with a strange knowing one day. He was also featured in prominent publications for his work and journey to one of the world’s largest portrait prizes, The Archibald Prize.

But now he prefers to imagine and make to change the world.

What is Oscar’s life Mission?

Oscar mission is to change the world with a pencil, pens and beautiful paper so that his imaginative tales and creations can be found in rooms, offices, buses and wall facades in town and cities large and small - so people awe at the ordinary.

A billion people on earth would be nice :) A beloved collection of children’s books too (that Roald Dahl would be proud of). Oh, and a film trilogy...

But I’d love to start (if you don’t mind) with you today!

● Have another questions? Contact Oscar here and he'd love to answer it!

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