Everybody loves a little bit of risk.

There is a thrill in stepping into the unknown—that quickening pulse, that sharp intake of breath—and then emerging safely on the other side. It unsettles us, pushes us off balance, nudges us beyond the familiar and opens the door to something unexpected—perhaps even transformative.

Flipside, presented by Esplanade – Theatres on the Bay is built on risk. We work with circus practitioners who perform extraordinary physical feats that take our breath away. We collaborate with artists who mine their personal histories, using their bodies and voices to tell intimate stories, crafting comedy and vulnerability for rooms full of strangers. And our audience take a risk too, choosing curiosity over certainty, arriving at the festival without knowing what to expect.

But risk is only half the story.

Risk exists because of trust. Trust is the quiet foundation beneath every leap, every catch, every moment of stillness before a fall. Behind every performance is a web of trust between artists, technicians and crew, holding each other with care so that the impossible becomes possible. Artists trust their instincts, sharpened by years of training and honing their craft; they know that when they take that leap, they will land.

This year is no different. From high-octane physicality to surreal absurdity, from deeply personal storytelling to communal spectacle, Flipside invites you into worlds that are daring, playful and deeply human. Across Esplanade from 29 May – 7 Jun 2026, artists test their limits, reimagine boundaries and draw us into shared moments of wonder.

At the Esplanade Theatre Studio, Australian circus company Gravity & Other Myths bring us into A Simple Space, an exhilarating, visceral experience watching acrobats push their physical limits to the extreme. In surrealistic Der Lauf (The Way Things Go) by Les Vélocimanes Associés, the audience must help a juggler with a bucket on his head navigate a series of absurd experiments. Local multi-hyphenate Dwayne Lau takes over the Esplanade Recital Studio for his first full-length performance at the festival with Snakes and Ladders!, sharing personal and heartfelt stories in his journey as an actor.

Taking the risk outdoors, Singapore’s very own Bornfire Circus returns with Sangam at the DBS Foundation Outdoor Theatre at Esplanade, tracing the journeys of diverse individuals overcoming daunting challenges in their search of new life. The ever-popular Aerial Open Stage returns for its seventh edition, welcoming 10 aerialists from Singapore and the region. We also meet charming Claudette, who teaches us that age is never a reason to stop taking risks or having fun. Lai Yee shares his story as a street artist in Hong Kong, bringing the audience on a meditative journey through the flow circus arts, including a fiery dragon staff. Gabez returns to Flipside after 14 years; masters of comedic alchemy, they create hilarity out of nothing but themselves. And all women circus from the UK, Circo Rum Baba, brings their Box of curiosities and surprises at unexpected corners of Esplanade.

We are grateful to Polar Premium Drinking Water for their generous support of the festival.

This is only a taster of what to expect at Flipside 2026! Since 2004, we have had the privilege of being a place where risk and trust meet—the collective gasps, the delighted laughter, the joy and playful spirit that resurfaces here year after year. We are deeply grateful for the artists, technicians, crew and audience who have taken that leap with us.

Please join us again. Take a risk, and we promise to catch you.

Lynn Yang
Assistant Head, Theatre
The Esplanade Co Ltd