Margaret Olley’s friendships with artists are chronicled in their pictures of her, such as William Dobell’s 1948 Archibald Prize–winning painting, works by Russell Drysdale and Jeffrey Smart and, much later, Ben Quilty’s 2011 Archibald Prize–winning portrait.

No other subject has won the Archibald twice (self-portraits by Brett Whiteley and William Robinson aside), and the 63-year span between Dobell’s and Quilty’s pictures is a true reflection of Olley’s enduring influence on other artists.

Olley had a great capacity for friendship, not only with other artists — with whom she made many convivial sketching and painting excursions — but also with supporters and dealers. These lifelong friendships were strengthened by a process of exchange and mutual recognition.

William Dobell Study for ‘Portrait of Margaret Olley’ 1948

William Dobell, Australia 1899–1970 / (Study for ‘Portrait of Margaret Olley’) 1948 / Gouache / 12 x 9cm / Ruth Komon Bequest, 2002 / Collection: National Gallery of Australia, Canberra / © William Dobell/Copyright Agency, 2019

William Dobell, Australia 1899–1970 / (Study for ‘Portrait of Margaret Olley’) 1948 / Gouache / 12 x 9cm / Ruth Komon Bequest, 2002 / Collection: National Gallery of Australia, Canberra / © William Dobell/Copyright Agency, 2019 / View full image

William Dobell ‘Margaret Olley’1948

William Dobell, Australia 1899–1970 / Margaret Olley 1948 / Oil on hardboard / 148 x 118.5 x 13cm / Purchased 1949 / Collection: Art Gallery New South Wales / © William Dobell/Copyright Agency, 2019

William Dobell, Australia 1899–1970 / Margaret Olley 1948 / Oil on hardboard / 148 x 118.5 x 13cm / Purchased 1949 / Collection: Art Gallery New South Wales / © William Dobell/Copyright Agency, 2019 / View full image

Margaret Olley & William Dobell 1965

Margaret Olley and William Dobell in ‘Painting People’ 1965 in front of William Dobell’s 1948 Archibald Prize–winning portrait of Olley / Still supplied by the National Film and Sound Archive of Australia’s Film Australia Collection / © NFSA

Margaret Olley and William Dobell in ‘Painting People’ 1965 in front of William Dobell’s 1948 Archibald Prize–winning portrait of Olley / Still supplied by the National Film and Sound Archive of Australia’s Film Australia Collection / © NFSA / View full image

Early friendships with artists in Sydney found expression in Dobell’s 1948 Archibald Prize–winning portrait Margaret Olley, which made Olley an unwilling art-world celebrity. Dobell picked Olley for his famous 1949 Archibald Prize–winning portrait after Loudon Sainthill had an exhibition at Macquarie Galleries in Sydney. He sent her an invitation saying, ‘Darling Olley, please come dressed as a duchess’. Fabric, however, was in short supply after the war — only parachute silk was available. Fellow artist Fred Jessup gave Olley the sleeves from his grandmother’s wedding dress, and she pieced them together with parachute silk to make herself an outfit. In the end, she was a very successful duchess. After the exhibition there was a party until dawn at Russell Drysdale’s place in Rose Bay. When Olley and Dobell were going back in the tram together to Circular Quay, he said he’d like to paint her. So she went along to his studio wearing an ordinary beige dress and one of her rather extravagant hats. She only had one sitting. When she finally saw the painting, Dobell painted her in the duchess dress.

Her friendships extended to a later generation, too, as she acquired the works of younger artists, including Cressida Campbell, Nicholas Harding and Ben Quilty.

Ben Quilty Sketches of Margaret Olley 2011

Ben Quilty’s sketches of Margaret Olley 2011 / © Ben Quilty

Ben Quilty’s sketches of Margaret Olley 2011 / © Ben Quilty / View full image

Ben Quilty, Australia b. 1973 / Margaret Olley 2011 / Etching on paper / © Ben Quilty

Ben Quilty, Australia b. 1973 / Margaret Olley 2011 / Etching on paper / © Ben Quilty / View full image

Ben Quilty ‘Margaret Olley’ 2011

Ben Quilty, Australia, b.1973 / Margaret Olley 2011 / Collection: Art Gallery of New South Wales / © Ben Quilty

Ben Quilty, Australia, b.1973 / Margaret Olley 2011 / Collection: Art Gallery of New South Wales / © Ben Quilty / View full image

Ben Quilty with Margaret Olley 2011

Portrait of Margaret Olley and Ben Quilty, 2011. Photograph: Tracey Nearmy. Image courtesy: AAP.

Portrait of Margaret Olley and Ben Quilty, 2011. Photograph: Tracey Nearmy. Image courtesy: AAP. / View full image

These artists, in turn, also created portraits of Olley, including Quilty’s 2011 depiction of her which, like Dobell’s before it, won the Archibald Prize. While Dobell’s portrait presents Olley in an almost full-length fancy dress and an elaborate hat, Quilty’s is an unflinching close-up of a sun-damaged and truthfully aged face. In both, Olley’s bright eyes command the viewer.

Olley liked Ben Quilty’s work, she judged Quilty in the Brett Whiteley Travelling Art Scholarship when he was only 29, she loved his thick use of paint. The Archibald Prize–winning portrait he made of Olley in 2011 just thrilled her so much. She said, ‘I’ve got life bookends — an Archibald at the beginning and an Archibald at the end’.

Ian Fairweather

Olley is also present in Ian Fairweather’s cryptically titled painting MO, PB and the ti-tree 1965, and was one of only a few people invited to visit the reclusive artist on Bribie Island. A bridge connecting Bribie Island to the mainland had opened in 1963, making the pilgrimage to Fairweather’s studio faster and easier for his artworld acquaintances. Olley respected Fairweather’s privacy, and only ever visited him with a few other people she felt would be of interest to the artist.

Ian Fairweather ‘MO, PB and the ti-tree’ 1965

Ian Fairweather, Scotland/Australia 1891–1974 / MO, PB and the ti-tree 1965 / Synthetic polymer paint on cardboard on hardboard / 87.7 x 113.3cm / Gift of Miss Pamela Bell 1996 / Collection: Queensland Art Gallery | Gallery / of Modern Art / © Ian Fairweather/Copyright Agency, 2019

Ian Fairweather, Scotland/Australia 1891–1974 / MO, PB and the ti-tree 1965 / Synthetic polymer paint on cardboard on hardboard / 87.7 x 113.3cm / Gift of Miss Pamela Bell 1996 / Collection: Queensland Art Gallery | Gallery / of Modern Art / © Ian Fairweather/Copyright Agency, 2019 / View full image

Russell Drysdale

Olley was a very popular figure in the Australian art scene, her portrait was painted by several Australian modernists. Olley was also the subject of Russell Drysdale’s portrait in 1948, the same year William Dobell won the Archibald Prize, while much later Jeffrey Smart would paint Second Study for Margaret Olley in the Louvre Museum 1994–95.

Russell Drysdale ‘Portrait of Margaret Olley in blue dress’ 1940s

Russell Drysdale, Australia 1912–81 / Portrait of Margaret Olley in blue dress c.late 1940s / Pen and wash on paper / 27.5 x 19.2cm / Bequest of Mrs I F Cantwell, 1990 / Collection: Macquarie University Art Collection / Photograph: Effy Alexakis, Photowrite / © Estate of Russell Drysdale

Russell Drysdale, Australia 1912–81 / Portrait of Margaret Olley in blue dress c.late 1940s / Pen and wash on paper / 27.5 x 19.2cm / Bequest of Mrs I F Cantwell, 1990 / Collection: Macquarie University Art Collection / Photograph: Effy Alexakis, Photowrite / © Estate of Russell Drysdale / View full image

Russell Drysdale Margaret Olley 1948

Russell Drysdale, Australia 1912–81 / Margaret Olley 1948 / Oil on canvas / 61.6 x 51.2cm / Gift of American Friends
of the National Gallery of Australia, Inc., New York, NY, USA, made possible with the generous support of Mr and Mrs Benno Schmidt of New York and Esperance, Western Australia, 1987 Collection: National Gallery of Australia, Canberra / © Estate of Russell Drysdale

Russell Drysdale, Australia 1912–81 / Margaret Olley 1948 / Oil on canvas / 61.6 x 51.2cm / Gift of American Friends
of the National Gallery of Australia, Inc., New York, NY, USA, made possible with the generous support of Mr and Mrs Benno Schmidt of New York and Esperance, Western Australia, 1987 Collection: National Gallery of Australia, Canberra / © Estate of Russell Drysdale / View full image

Jeffrey Smart ‘Head study for portrait of Margaret Olley’ 1994

Jeffrey Smart, Australia/Italy 1921–2013 / Head study for portrait of Margaret Olley 1994 / Pencil on paper / 39 x 29cm / Bequest of Nick Enright AM 2004 / Collection: National Portrait Gallery, Canberra / © Estate of Jeffrey Smart

Jeffrey Smart, Australia/Italy 1921–2013 / Head study for portrait of Margaret Olley 1994 / Pencil on paper / 39 x 29cm / Bequest of Nick Enright AM 2004 / Collection: National Portrait Gallery, Canberra / © Estate of Jeffrey Smart / View full image

Jeffrey Smart ‘Margaret Olley in the Louvre Museum’ 1994–95

Jeffrey Smart, Australia/Italy 1921–2013 / Margaret Olley in the Louvre Museum 1994–95 / Oil on canvas / 67 x 110cm / Bequest of Ian Whalland 1997 / Collection: Art Gallery / of New South Wales, Sydney / © Estate of Jeffrey Smart

Jeffrey Smart, Australia/Italy 1921–2013 / Margaret Olley in the Louvre Museum 1994–95 / Oil on canvas / 67 x 110cm / Bequest of Ian Whalland 1997 / Collection: Art Gallery / of New South Wales, Sydney / © Estate of Jeffrey Smart / View full image

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