In January 1985, a little bird flew into Billy Connolly’s life. At least that’s the way the Big Yin puts it.

Connolly was beginning his Australian tour with a series of shows at the Sydney Opera House, and one night his Glasgow-born mate Mark Knopfler joined him on stage. After the show, Knopfler introduced the funnyman to a member of the audience – “Australia’s greatest living artist, although I didn’t know it at the time.”

After a lifetime of getting hammered and waking up wearing an internal balaclava, the former shipyard welder was giving grog a rest. The trio nevertheless retreated to a hotel bar, where the comedian, the painter and the guitarist proceeded to get along like a house on fire. The guy with the curly hair was a great laugh with “a lust for life”. He asked Billy if he did the same material every night. Billy said no, that he just riffed on a few favourite subjects. Whiteley bet him five dollars that he couldn’t do a completely different show the next night.

Billy accepted the challenge and duly won the bet. Whiteley handed over the fiver and said, “See you again tomorrow.” Connolly was famous for losing track of time while on stage. He’d once talked for over four hours, leaving the audience locked out of the car park. “Bugger off,” he told Whiteley. “Nobody’s got six hours.”

Next day, Knopfler took him around to Whiteley’s new studio, an old T-shirt factory in Surry Hills. He thought the artist’s work was brill. Whiteley imitated a bowerbird eyeing off, then snatching, a shiny blue marble. Connolly was enormously chuffed to see his photograph hanging among Whiteley’s collection of favourite faces.

Whiteley was then at the pinnacle of his fame. Over a 25-year career he had made an indelible impression on Australia, creating an instantly recognisable body of work as fluid, exotic and occasionally grotesque as the Sydney that his art and uninhibited lifestyle seemed to embody.

Ten years after his first visit, Connolly returned to Whiteley’s studio. He had come to shoot a sequence for his World Tour of Australia television show. “He changed my life forever,” Connolly told his viewers as he capered enthusiastically around the artworks.

Whiteley wasn’t there, of course. He’d died three years earlier, at the age of 53. Connolly remains, on all available evidence, indestructible.

Shane Maloney and Chris Grosz

Shane Maloney is a writer and the author of the award-winning Murray Whelan series of crime novels. His 'Encounters', illustrated by Chris Grosz, have been published in a collection, Australian Encounters.

Chris Grosz is a book illustrator, painter and political cartoonist. He has illustrated newspapers and magazines such as the Age, the Bulletin and Time.