By Cayman Compass contributor Christopher Tobutt
The final evening of the Cool Out 2026 event settled over Cayman Cabana with the kind of ease that only happens when a long week of ideas finally exhales into music.
After days of panels, workshops, and creative industry conversations stretching from the new Endless Sea Studio to venues across George Town, Fish Tea Vibes on 14 Feb. felt like the moment when everything softened into community. The sea kept its slow rhythm behind the stage, families drifted in from the street, and the night began with the bright, chiming optimism of the Cayman International School Steel Pan Ensemble, their medley ringing out over the water like a welcome.
Shenna Lee followed, stepping into the evening with the confidence of someone who has been performing across Cayman for 15 years. Before her set, she said she wants her music to be ‘soul, but with soca flavourings’. Onstage, that blend came alive. Her originals, ‘Whistle for Me’ and ‘Without You’, carried a warm, contemporary sheen, while her covers – Rihanna’s ‘Love on the Brain’ and Olivier Dean’s ‘Man I Need’ – showed the range and polish of a seasoned vocalist. She kept things joyful, but there was substance beneath the shine.
That thread – the insistence on something real beneath the surface – became the quiet theme of the night. It was most explicit in Kyle Matrixx’s set, which opened with a hard-hitting rap about identity. His verses pressed into the tension of being Jamaican born and Cayman raised: not Jamaican enough, not Caymanian enough, the unspoken rule that you’re not a “real Caymanian” unless your family goes back three generations, and yet, not fully part of the Jamaican dancehall world either.
Kyle refused all of it. His message was simple and powerful: he would define himself, not wait for others to do it. From there, he shifted into two songs about love – not the glossy Valentine’s Day version, but the complicated, ambiguous kind that lives in real relationships. His beats changed shape, moods turning on a dime, mirroring the emotional terrain he was navigating.
Yahsave carried that same urgency into a different register. Even when the lyrics blurred into the night air, the intention was unmistakable. His very name – echoing “Yahweh saves” – hints at spiritual depth, and his delivery felt like an Old Testament prophet wrestling divine truth into the open.
Later in the evening, Colindra-Rodericka McGarvey-Sterling added her own expressive voice, and Madam Nirosa – singer, songwriter, painter, dancer — brought a multidisciplinary fire that felt both contemporary and ancient, her movements and vocals blurring into something ritualistic. She also brought one of her original paintings for all the artists to sign.
Then there was Daniel Augustine, blending drums and percussion into a rhythmic architecture of island pride.
Threaded through it all were the musicians who held the night together: bassist Jonathan McDonald kept the groove smooth; drummer Lamas Dennis gave the evening its heartbeat; and James Munroe Jr., a gifted keyboardist and emcee, guided the flow with easy charm.
By the time the final notes drifted out over the water, the night had revealed itself: a gathering of artists determined to keep it real – in their lyrics, in their stories and in their sense of who they are becoming. For a few hours on the waterfront, Cayman’s creative pulse was unmistakably alive.
Christopher Tobutt is a freelance journalist who has written for various publications in the Cayman Islands since 2003.
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