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The harbour city has witnessed everything from convict times to the bloody gang wars to the multi-cultural metropolis it is today. Some of Australia’s greatest authors and film-makers have been inspired to create their portrait of Sydney. Here are just a few tales that show their different perspectives.

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Unreliable Memoirs by Clive James (1981)

In the first volume of James’ autobiography, the ‘Kid from Kogarah’ recounts his days growing up in the suburbs of post-war Sydney. His adventures, covering his first 22 years, are hilariously told with a self-depreciating humour that makes you cringe and laugh at the same time.

Emerald City by David Williamson (1987)

This story by Australia’s best known playwright gave Sydney its nickname. It’s a satirical commentary on the materialism of the 1980s, delivered with no-holds-barred wit. Featuring a couple in the film and publishing industries, it’s a commentary on the values and morals of the time.

Razor: Tilly Devine, Kate Leigh and the Razor Gangs by Larry Writer (2001)

In 1920s and '30s Sydney, some of Australia’s worst criminals in history defended their territories violently. This fascinating true story of vice-queens Tilly Devine and Kate Leigh, brings the city's dark past back to life. The book also became part of the ‘Underbelly’ TV series.

Five Bells by Gail Jones (2011)

A love letter to Sydney and its beauty, Circular Quay and the Sydney Opera House provide the focal point for this narrative about four characters from very different worlds, each with their own emotional baggage, told over the course of one day in the city.

Thirty days in Sydney by Peter Carey (2001) 

Non-Sydneysiders are likely to be both intrigued and appalled by the city as Carey portrays it. Subtitled “a wildly distorted account”, returning as an expat, he writes poignantly about the city’s beauty and ugliness; reuniting with old friends who define Sydney through their stories. 

Watch

The Sentimental Bloke (1919) 

This Australian silent film, based on the 1915 poem The Songs of a Sentimental Bloke by C. J. Dennis, tells the tale of an ordinary bloke whose life is transformed by love. Step back in time to the olden days of Woolloomooloo, Manly and Bondi.

The Matrix (1999) 

While not technically about Sydney, keep a close eye on the background and you’ll see the futuristic metropolis of Mega City was actually created around the suburbs of Balmain, Chippendale, Hyde Park, Moore Park, Millers Point, Pittwater, Broken Bay, Redfern, Rozelle, Surry Hills and Waterloo. 

Erskineville Kings (1999) 

This earthy film, starring Hugh Jackman, is the story of two brothers, reunited after one has escaped an abusive father, and the other who stayed home to look after him. Beautifully shot with images of dirty back alleys and rundown buildings of (then) suburban Erskineville.

Looking for Alibrandi (2000) 

Based on the book of the same name, this award-winning feature is about a teenage girl in her final year at a wealthy Catholic high school, dealing with the traumas and relationships of everyday life. It received praise for its insights into the second-generation-migrant experience.

Bondi Rescue (2006–) 

Ask anyone to name an Australian beach and chances are the response is Bondi. See how the real life lifeguards spend their summer on the famous beach. David Hasselhoff, Hugh Grant, Rowan Atkinson, Paris Hilton, Russell Crowe and Richard Branson have also made celebrity appearances.