We acknowledge the Gadigal of the Eora Nation, the traditional custodians of the Country on which the Art Gallery of NSW stands.

Winner: People's Choice 2000

Esther Erlich Never been better

acrylic on canvas

198 x 76 cm

In 1999, Esther Erlich painted a pair of jeans for Jeans for Genes at the Museum of Contemporary Art – and so did Bill Leak. Erlich had imagined the renowned cartoonist/painter to be a little old man and was surprised to discover that he was very tall, not old and extremely charming. Emboldened, she asked if he would sit for a portrait and he agreed.

‘He was lovely,’ she says. ‘Very modest and charming but he looked terribly serious in so many of the poses which isn’t him. Then he pulled a hilarious face. I took a shot and thought, “That’s the one!”’ The title of the painting relates, she says, to Leak’s philosophy on life.

Erlich wanted to paint Leak life-size. Since he is so tall and she is so comparatively short, that meant standing on a crate. Other than that, she says, the painting happened pretty easily.

Born in Australia, Erlich has exhibited around the country since 1983. She won the Doug Moran National Portrait Prize in 1998.