Review: Kerry Hiles Shines as Judy Garland in A Star Is Born at Theatre on the Square

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I had the immense pleasure of attending A Star Is Born – The Rise and Fall of Judy Garland at the Theatre on the Square, and let me just say, Kerry Hiles blew me away! If you think you know Judy Garland’s life, think again. This beautifully crafted cabaret doesn’t just tell you her story but brings you right into the heart of her world with timeless songs and poignant moments.

From the moment Kerry Hiles walked on stage, I was captivated. She doesn’t just impersonate Garland during certain sections, but instead embodies the spirit of her life with grace and power. Accompanied by the incredibly talented Luke Holder on piano, Hiles took us on a 70-minute journey that highlighted both the glitz and the heartbreak of Garland’s life. You could feel the weight of the stories behind the songs, and yet, there was also so much joy, humour, and passion-infused into every number.

The performance was packed with Garland’s iconic hits, from “Over the Rainbow” to “The Trolley Song,” and even some delightful surprises like “Hoe Down.” Each song felt like its own little vignette, punctuating the highs and lows of Judy’s life. But what really struck me was how effortlessly Hiles navigated the emotional terrain. One minute, I was basking in the pure joy of “I Got Rhythm,” and the next, I was caught in the bittersweet melancholy of “The Man That Got Away.” It was a rollercoaster of emotions, and I loved every second.

Hiles lived Judy’s story on stage. Her smile lit up the entire theatre, and her voice was simply stunning—full of depth, vulnerability, and control. There’s a certain elegance and warmth in how she connected with the audience, making it feel as if we were sitting in a living room hearing these intimate tales for the first time.

One of the standout moments for me was the performance of “If You Feel Like Singing, Sing.” The sheer joy in Hiles’ voice was infectious, and it felt like an invitation for all of us to celebrate life despite its hardships—a sentiment that perfectly captures Judy Garland’s essence. It was a beautiful reminder that even in her darkest moments, Garland never stopped performing, never stopped entertaining.

Would I go again? Absolutely. In fact, I’d happily watch it twice, if only to soak up even more of the nuanced performances and gorgeous storytelling. Kerry Hiles’ portrayal of Judy Garland is both a tribute and a masterclass in cabaret. If you have the chance to see A Star Is Born – The Rise and Fall of Judy Garland, don’t miss it—it’s a performance that will stay with you long after the final note is sung.