The best shows to see in Sydney this month

Apparently, books are dying. Fortunately, Garry Starr is here to save them. Fresh from a sold-out run in London’s West End and winner of the Melbourne International Comedy Festival’s Most Outstanding Show in 2025, comic mastermind Damien Warren-Smith once again transforms into his chaotic alter ego in Garry Starr: Classic Penguins. The show lands at Carriageworks this winter with a literary adventure that’s as absurd as it is laugh-out-loud funny. Armed with little more than a tailcoat, a pair of penguin flippers – and an alarming lack of clothing – Starr sets himself an impossible mission: to perform a whole heap of Penguin Classic novels in under an hour. 

Time Out Sydney Editor Avril Treasure saw Classic Penguins last year at Redfern’s Grand Electric and says: “I don’t really like using the term ‘must-watch’, but this absurd, ridiculous, laugh-until-you-cry show is exactly that. Starr goes all-in, bush and all, in this not suitable for children homage to Penguin Classics – the funniest, silliest show I’ve seen.”

I had high expectations – I won’t lie. As a literary and theatre purist, I am always a little wary of adaptations, but the mix of Y2K child star culture with Shakespeare’s Macbeth had me curious. I mean, what could explore power and unchecked ambition more than the kingdom of Hollywood? Virginia Gay’s modern adaptation, Mackenzie, not only raised the bar but crushed it into rhinestones and scattered it across the stage. This fabulous Bell Shakespeare production, now on at The Neilson Nutshell in Walsh Bay, plays with power without ever wavering from its camp and comedic register. Gay has reminded us that camp, done right, is that serious.

Hop into the passenger seat and settle in for a road trip unlike any other. Making its Australian debut at the Sydney Opera House this June, Truck Driver is a compelling one-person play written and performed by multidisciplinary artist Jonny Hawkins (AKA Aunty Jonny), a familiar figure in Sydney’s nightlife and arts scene. Over 75 minutes, audiences are invited to travel shotgun alongside Bev, a fifth-generation owner-operator long-haul truck driver whose colourful stories, rough-around-the-edges humour and deeply ingrained beliefs reveal a complex portrait of contemporary Australian masculinity. So, buckle up and come along for the ride.

The opening note of ‘The Circle of Life’ may just be one of the most recognisable in a Disney musical. If you don’t agree, then you may have to convince the entire theatre-going audience who were at Disney’s The Lion King on opening night. The full house’s roars could be heard all the way out of the Capitol Theatre’s front doors as the king of musicals triumphantly returns to Sydney – the first time in more than a decade.

Anastasia (1997) was among the first musical films I knew in its entirety. While many children frolicked to Timon and Pumbaa’s playful anthem in The Lion King, I was instead reenacting “Once Upon a December” in my living room, captivated by a heroine whose quiet determination carried her through danger and uncertainty. At the time, I could not have anticipated how deeply this film would shape my relationship with musical theatre. “Journey to the Past” soon became a staple audition piece, and Anya’s unwavering belief in her own worth quietly informed my own developing sense of confidence.