Things to do in Sydney in May

If the leading lady of a daytime telenovela was to read too many pop-psychology books while downing a double Espresso Martini, you might get something close to Women on the Verge of a Nervous Breakdown. This musical comedy based on Pedro Almodóvar’s 1988 cinema cult classic is given a neon-lit, red-curtained makeover at Sydney’s Hayes Theatre. With precision taking a backseat to passion, director Alexander Berlage (Cry-Baby, American Psycho) delivers a stylish descent into screwball mania. The action takes place in Madrid, Spain, where Amy Hack’s (Yentl) heartbroken actress, Pepa, is having a terrible, very bad day, which we see play out from depressive start to high-flung resolution. Her lover Iván breaks up with her over answering machine, and thus, her Odyssey-styled mission to find and confront him begins. Along the journey, Pepa butts heads with Iván’s scorned ex-wife Lucia (Tisha Keleman), his son and his own frustrated fiancée, as well as her wildly unravelling best friend, Candela (Grace Driscoll).  With a book by Jeffrey Lane (known for his musical adaption of Dirty Rotten Scoundrels) and music and lyrics by David Yazbek (Dead Outlaw), the original Broadway production of Women on the Verge had a relatively short lifespan – closing soon after it received poor reviews, and even poorer ticket sales. This is where Berlage’s adept hand at re-inventing cult flops takes charge – finding a space for his avant-garde style through sharp angles, frenetic choreography, and...

For a few special days every year, Sydney comes alive with writers, journalists, public intellectuals and book lovers – who gather for the Emerald City’s long-standing celebration of literature, reading and ideas: the Sydney Writers' Festival. This year marks the 28th birthday for our city’s most beloved celebration of words, and the festival’s 2025 theme is In This Together: a theme that emphasizes the power that literature has to connect us. Featuring more than 200 events, and welcoming more than 40 international guests as well as more than 100 Australian authors, this year’s festival will bring fascinating conversations to Sydney from Monday, May 19 until Tuesday, May 27. The beloved Inner City arts centre Carriageworks will act as the hub for this year’s festival, with additional events  popping up at Sydney Town Hall and The State Library of NSW.Big names taking to the stage for this year’s event include David Nicholls and Liane Moriarty (who will appear in-conversation), Jeanette Winterson (who will be celebrating the 40th anniversary of her landmark novel Oranges Are Not The Only Fruit), Marian Keyes and the incredibly insightful philosopher A.C. Grayling.If you’re on a starving artist budget, fear not: the program features more than 50 free events (with 30 taking place at Carriageworks) including a lecture series examining topics ranging from China’s cultural revolution to the shape of Australian politics.  For budding writers and readers, there’s a whole day...

Yeehaw! A boot scootin’ mini fest is going down this May in the Inner West’s breweries – just BYO cowboy hat. Running over two more weekends (May 17-18 and 24-25), the Inner West Country Fest will see the beer houses on the Inner West Ale Trail turn up the volume with a soundtrack of country, hip hop, rockabilly, reggae and retro hits, backed up with cracking food, drinks and family-friendly experiences. From laneway parties to First Nations DJ sessions, line dancing and barbecue cook-offs – if you’re looking for something fun to do this month, this is it. Highlights include Newtown’s Young Henrys teaming up with First Nations creative collective Awesome Black (Sat, May 17) for a powerful line-up of ten First Nations artists, DJs and cultural performances. Been a while since you let your hair down? Wayward Brewing Co will be throwing a laneway party (Sat, May 24) featuring live bands, lotsa dancing and cold beer. The flames will be roaring at Future Brewing (Sat, May 24), with Sydney favourite Mitch Orr cooking alongside one of the world’s best barbecue pitmasters, Jo Chew, for a delicious country cookout and community fest. Get out your sweatbands as The Bob Hawke Beer & Leisure Centre travels back in time with an ’80s party (Sun, May 18) – think retro vibes, old-school bangers and, of course, a succulent Chinese meal. Mixtape is also getting in on the fun, hosting a night of live music at the Rockin’ Rodeo Concert (Fri, May 16), Wildflower Brewing & Blending will be...

If you’re of a certain age, you have history (HIStory, perhaps?) with Michael Jackson. I remember getting ‘Thriller’ on cassette as a kid. ‘Dangerous’ was one of the first CDs I ever owned. I remember seeing the extended music video for ‘Thriller’ on VHS, which came packaged with a behind-the-scenes documentary. One woman, cornered for a quick vox pop at one of the filming locations, asserted that she loved Jackson because he was “down to earth”, which is darkly hilarious in hindsight.  Down to earth? The press called him “wacko Jacko” – we all did. He slept in a hyperbaric chamber. He owned the Elephant Man’s skeleton. His skin kept getting paler, his nose thinner. What a weird guy! Was any of it true? Hard to say. Even today, when a careless tweet is like a drop of blood in a shark tank to fans and journos alike, the media furor around Michael Jackson stands as one of the most frenetic in living memory, eclipsing the likes of Beatlemania. Jackson wasn’t bigger than God, he was God to a lot of people – the King of Pop, the first Black artist to smash through the MTV colour barrier, an artist, an icon, a living legend. Then came the allegations of child sexual abuse, which first began in August 1993, and continue to this day. For those who were still on the fence, the documentary Leaving Neverland, released in 2019, saw many more fans abandon Jackson, who died in 2009 at the age of 50. And so, it makes sense that MJ the Musical would set Jackson’s relationship with the...

Ever wondered what Sydney would have looked like without all the clustered skyscrapers, scenic foreshores and sprawling suburbs? Seeing Sydney, Knowing Country strips the Harbour City right back to reveal the land as it once was. Running until November, the exhibition at the Museum of Sydney shows how the British colony took shape — and how knowledge of Country has continued to shape Sydney across generations. Travel back to the late 18th century when Governor Arthur Philip drew Sydney’s first boundary line in the sand of what we call Manly Cove. This marked the beginning of dispossession from the First Nations peoples after 60,000-plus years of custodianship of the land. The first land grant issued in the colony is one of many artefacts, sketches, plans and objects in this fascinating collection.  This free exhibition was created in collaboration with artist and designer Alison Page, a proud descendant of the Dharawal and Yuin peoples. Through her Aboriginal design agency and roles on numerous cultural boards, Page is a leading voice in contemporary Indigenous art and storytelling. Her innovative artistic intervention runs throughout the exhibition, layering First Nations understandings of Country over the colonial view of Sydney’s past. The exhibition was also developed in collaboration with the Sydney Coastal Aboriginal Women's Group.  Seeing Sydney, Knowing Country is open seven days a week at the Museum of Sydney until November. Find out more about this free...

Australia’s most popular arts event is back in action for 2025, with the Archibald, Wynne and Sulman Prizes bringing a fresh batch of painterly expressions to the walls of the Art Gallery of NSW from May 10 to August 17.  They call it “the face that stops the nation”, and the Archibald Prize has indeed been courting controversy and conversation for more than a century now. This popular portrait prize is always filled with famous faces, with artists from all over Australia (and also New Zealand) capturing the spirit of the times through paintings that capture the likeness of the personalities that define their communities. Julie Fragar is the winner of the 2025 Archibald Prize – she won over the judges with a stunning portrait of fellow artist Justene Williams (read more). RECOMMENDED: A beginner's guide to the Archibald Prize. The winner of the 2025 Packing Room Prize was announced a week earlier, with the Packing Room Pickers (a.k.a. the Art Gallery staff who receive, unpack and hang the entries) selecting Abdul Abdullah's striking painting of fellow finalist Jason Phu as their favourite Archibald portrait this year (read more here). Meanwhile, the Wynne Prize awards the best landscape painting of Australian scenery or figurative sculpture, and the Sulman is awarded to the best genre painting, subject painting or mural project. (Find out more about the 2025 winners over here.) The annual finalists exhibition is a real must-see, with each prize attracting diverse entries...

What does it take to choose your values and beliefs over those of others, and to fight for them? What does it take for a woman to be defiant – to go against what is expected of her, and perhaps even go against her own family? Fresh off an international tour of his critically-acclaimed three-hour epic Counting and Cracking (which included a special sold-out season at Sydney’s Carriageworks), S. Shakthidharan returns to the Belvoir stage with another powerful chapter of South Asian history. Detouring from the grand scale of Counting and Cracking and Shakthidharan’s follow-up show, The Jungle and the Sea, this restrained 90-minute fable is told through the perspectives of four defiant women, each of them shaped by differing values, ideologies, survival and sacrifice.  The Wrong Gods is a work of protest – it’s angry, sad, and deeply unsettled by the relentlessness of capitalism The Wrong Gods imagines the protests surrounding the controversial Narmada Valley dam project. Initiated in the late 1980s, the dam is one of the world’s largest hydropower infrastructure projects. It was intended to supply electricity and drinking water to three Indian states, but its legacy is fraught – thousands of indigenous people and villagers were displaced, ecosystems were irreversibly altered and damaged, and the project remains at the centre of sustained protests. Nirmala (Nadie Kammallaweera, who appeared in both Counting and Cracking and The Jungle and the Sea) a farmer and the head of the...

Hold on to your alibis, dear readers. Hot on the heels of the recent national tour of The Mousetrap, another classic from Agatha Christie’s playbook of murder mystery mayhem lands on the stage at Sydney’s Theatre Royal.  *** Time Out Melbourne reviewed And Then There Were None when it played at the Comedy Theatre in February. Read on for that three-star review:   Somewhere off the coast of Devon is a dreary little island with high cliffs, higher tides and no way to escape. It’s Soldier Island: a lovely place to put your feet up, take a dip, meet nine strangers and watch as you all get slowly picked off one-by-one. This is the wickedly thrilling premise of Agatha Christie’s 1939 classic And Then There Were None. A favourite among Christie fans (and Christie herself), it arrives in a production that once again proves that the master of the whodunnit can still thrill us nearly 100 years on. Yet, this revival from director Robyn Nevin – her second of Christie’s following 2023’s The Mousetrap – rests on the laurels of its author too often, offering a passable but ultimately thin restaging that I think might signal the end of the recent resurgence of British classics in our theatres. It’s 1939. Ten people have been invited to Soldier Island under suspicious pretences. They have little in common apart from the skeletons in their closets. For much of the show’s bloated first act, we’re watching this motley crew of potential victims introduce themselves to each other. Christie is...

Just over a decade since it was last seen in Australia, Annie is back – bursting onto the Capitol Theatre stage filled with optimism, joy, and hope. Director Karen Mortimer revives this quintessential piece of musical theatre with a sentimental production that preserves the charm and flair found in Thomas Meehan’s book. For those living under a rock (mainly me), this Tony Award-winning musical follows the story of 11-year-old Annie, who is growing up in an orphanage in 1930s New York, under the cruel eye of Miss Hannigan. In the midst of the Great Depression, pessimism is all around, but chipper young Annie has the antidote: hope. Encouraging others to believe that “the sun will come out tomorrow”, Annie’s enduringly positive spirit seems to finally pay off, when billionaire Oliver Warbucks chooses to take her in for two weeks over Christmas. Four spirited young performers share the titular role in this production, alongside an alternating cast of child actors. On opening night, Dakota Chanel’s Annie is a ray of sunshine, fully embodying the doe-eyed optimism of the character, balancing warmth and comedy with the more tender and emotional segments. The whole ensemble of “orphans” share an incredible chemistry, which is strongly on display in their performance of ‘It’s The Hard Knock Life’. The stakes are high when it comes to such a well-known and well-loved song, but this ensemble more than meets the challenge with a passionate and committed performance.  Annie is the...

Samuel Beckett’s Winnie, the hapless, half-buried heroine of his 1961 play, Happy Days, is one of those pinnacle roles in theatre. Comparisons to Hamlet are common, but apt. It’s such an actor’s role that it makes sense, arguably with certain caveats, that the actor in question takes up at least one directorial rein. It certainly makes sense to Sydney Theatre Company, who are giving us the legendary Pamela Rabe (Belvoir’s August: Osage County) directed by Pamela Rabe (and Nick Schlieper) in this production. Winnie (Rabe) is immured in a mound of earth up to her waist. She wears what might be a faded ball gown. Harsh light beats down on the dark ground (which looks hand-painted) and a kind of horizontal proscenium structure is reminiscent of a CinemaScope screen or the jagged glow of a flatscreen TV, further heightening the sense of artificiality – or at least, a kind of constructed reality. But Winnie is all too human and real. She fends off the sun’s rays with a broken umbrella, she comments on her station (although we’re never given much context in regards to how she got where we find her), she chats with her laconic husband, Willie (a fantastic and funny physical performance from Markus Hamilton) who occasionally drags himself onto the stage, but rarely into her field of vision. Above all else, she tries to maintain an upbeat attitude, repeatedly declaring this to be yet another “happy day”. Even after the second act arrives, following a dark and ominous interlude...