Jamie Preisz has won this year’s Packing Room Prize, worth $1500 for a portrait of Jimmy Barnes called Jimmy (title fight) – which means that unless he makes history, he won’t be taking home this year’s Archibald Prize, for thus far never the twain have met. It is, however, the first time that the new Head Packer Brett Cuthbertson has awarded the Prize.

Jimmy Barnes with artist Jamie Preisz. Photograph © Art Gallery of New South Wales

Preisz said that he was inspired in part to paint Barnes’ photograph because of his fighting attitude and because of the death of his own sister Bella. “After losing my sister to suicide, I was touched deeply when I saw an interview with Jimmy speaking about his own suicide attempt. To me, he was fighting against the stigma of mental health issues by speaking so publicly about his own struggles, especially to generations of men who don’t feel that having emotional intelligence is a masculine quality,” said Preisz in his label.

Meryl Tankard painted by Dee Smart. Photograph © Art Gallery of New South Wales

This year, a huge 58 finalists were announced in the Archibald Prize, which first took place in 1921 and is now worth $100,00. There are 22 artists represented in the Archibald for the first time, along with five previous winners – Del Kathryn Barton, Nicholas Harding, Euan MacLeod, Guy Maestri and Marcus Wills. This is the 18th time that Harding – who has painted himself being treated for cancer – has been an Archibald finalist, while Robert Hannaford is there for the 20th time. He too painted a self-portrait – one of 19 artists who painted themselves.

Guy Pearce painted by Anne Middleton. Photograph © Art Gallery of New South Wales

Dancer/choreographer Meryl Tankard, painted by Dee Smart, is seen wearing knickers on her head – which she did when she performed in a production for Pina Bausch. There are also portraits of actors Guy Pearce (by Anne Middleton), David Wenham (by Jordan Robertson), Nicholas Hope (by Loribelle Spirovski) and Alison Whyte (by Paul Jackson); singer Courtney Barnett (by Melissa Grisancich); author Richard Flanagan (by Julian Meagher); and New South Wales Arts Minister, The Honourable Don Harwin (by Mirra Whale).

Amani Haydar in her painting Insert headline here. Photograph © Art Gallery of New South Wales

In a moving painting, lawyer Amani Haydar paints herself holding a newspaper article of her own mother, who was murdered by her abusive father. Haydar’s mother is holding a photograph of her own mother, who was killed in an Israeli airstrike fleeing the southern villages of Lebanon. “By painting a self-portrait, I was able to reinstate its personal significance to me,” she says in her label, adding that it was “a way of reclaiming my story from the headlines”.

This year, after complaints about the gender balance in the past, women feature in 30 of the 58 Archibald paintings.

The finalists for the Wynne and Sulman Prizes have also been announced. The winners will be revealed on Friday May 11.