Cassie Hamilton and Green Door Productions unleash one of the most exciting, form‑shifting new musicals to hit Sydney in years.
When: 26 March – 11 April 2026

The Old Fitz Theatre has an uncanny knack for spotting the artists who are about to detonate something exciting in Australian Indie theatre. It’s one of the few spaces where you can walk down those narrow basement stairs and genuinely not know what you’re about to encounter, only that it will be bold, contemporary and unafraid of sharp edges. Their programming continues to champion work that pushes form, politics and performance into new territory.
A Transgender Woman on the Internet, Crying hits that ethos like a neon grenade. Playwright Cassie Hamilton fuses hyperpop energy with razor‑sharp satire in a queer musical dramedy that’s part digital send‑up, part emotional freefall. It’s a glitch‑bright dive into becoming — ferocious, brave and brilliant.
Avis O’Hara, the internet’s most fabulous trans influencer, floats through life with full Disney‑princess vibes and a perfectly curated persona. Corrin Verbeck, an ultra‑cool left‑tube vlogger, is determined to expose her as the “wrong kind of trans.” This is the core of the story: in‑community gatekeeping – the purity tests, the aesthetic scorecards, the sideways judgments about who’s doing transness “properly.” The ring lights, livestream spirals, vibrating phones and algorithmic mood swings may be of this moment, but the emotional stakes reach far beyond it.
Structurally, this new musical runs like a live feed mutating in real time, scenes shifting between confession, comedy and collapse with each flick of the scroll. Built for the niche who live inside the discourse, it also welcomes anyone curious enough to enter – or even attempt to understand – the “new enlightenment”: that wild online awakening after one TikTok, one thread or one cancellation cycle, where gender fluidity, identity play and self‑reinvention move as fast as the feed itself. What follows is a digital‑pop delirium, a beat‑box rap with heart, in a world where everything is mildly affirming but generally offensive.
“ – hits that ethos and the Old Fitz space like a neon grenade….A glitch‑bright dive into becoming — ferocious, brave and brilliant.”
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Director Jean Tong hits every beat, shaping an atmosphere as savvy, sarcastic and quick‑witted as the characters themselves. Normally the bio box is where you clock the mechanics – the neat timing, the clean cues – but here it feels more like a pulse point, a dance‑party control booth where each scene thinks, tightens and reacts in real time.
Hamilton is the force behind the engine. She wrote the book, music and lyrics, and her onstage alter ego drives the show, with a score that moves like the internet itself: pop bursts, glitchy ballads, meme‑coded refrains and sudden drops into something raw and unguarded.There’s a touch of Hamilton‑style rap‑poetry in the way some numbers punch and tumble, but the voice is unmistakably her own. She has a producer’s instinct, letting the music swell, crack and soften toward real tenderness.
The cast ride that emotional ricochet and razor‑edged humour with real dexterity, flipping from comedy to crisis to clarity in a heartbeat, their voices catching every spike, scroll and sudden plunge the music demands – pop flashes, glitch‑soft ballads and sharp little hooks shifting underfoot.They manage the Old Fitz’s acoustically modest space with finesse, finding nuance and range.


At the centre are two trans femmes who shouldn’t work on paper but spark like Lizzy Bennet clocking Darcy across a crowded algorithm – all friction, wit and accidental longing. Cassie Hamilton and Blake Appelqvist build an opposites‑attract romance that’s messy, magnetic and unmistakably modern, the kind of connection that feels both inevitable and entirely undeserved in the best rom‑com way. Their chemistry is quick, clever and unexpectedly touching during their duets.
Rosie Rai and Teo Vergara slip between hype‑squad, truth‑teller and digital phantom, embodying the internet’s chorus: the friends, the trolls, the algorithmic ghosts, all the shifting forces nudging the central couple toward clarity or collapse. Rai’s snark is brilliantly barbed, but there’s a vulnerable pulse beneath it that catches you off‑guard when the mask slips. Vergara brings a steadier gravitational pull, grounding the emotional whiplash even as they shift personas.
For all its glitch and full‑tilt sensory overload, A Transgender Woman on the Internet, Crying nails the reality of digital‑age living and gender: identity performed, performance weaponised, survival reclaimed, and the joy of pretty imperfection insisting on its place anyway. A fierce, generous work that advances the conversation while keeping its heart exactly where it belongs. Musical theatre sit up and take notice — you should have seen this one coming.
A Transgender Woman on the Internet, Crying runs from 26 March – 11 April at The Old Fitz Theatre.
For details see : https://www.oldfitztheatre.com.au/a-transgender-woman-on-the-internet-crying
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Photo Credit: Brett Boardman


