Kaiso Street Society Launches “Calypso in the Air”
A Sonic Takeover for Calypso History Month
Month-long campaign brings Calypso’s legacy into everyday spaces through playlists, podcasts, and performances
TORONTO, September 2, 2025 – This October, Kaiso Street Society (KSS) invites audiences across Canada and the Caribbean to tune in, turn up, and celebrate Calypso like never before. The collective is launching “Calypso in the Air,” a month-long audio and media campaign designed to infuse community spaces, radio waves, and digital platforms with the vibrant sounds and stories of Calypso.
Through curated playlists, live performances, podcast episodes, and online content, the campaign highlights Calypso’s power as both cultural memory and cultural movement. Each week features fresh ways for audiences to experience the music, from learning its history to dancing to its future.
“Calypso isn’t just nostalgia—its ethos is alive, evolving, and speaking to today’s world,” says Jesse Ryan, musician and founder of Kaiso Street Society. “There is history there, across the diaspora — and there is history here, in Canada. Calypso in the Air brings both stories to the forefront.”
The campaign will feature weekly themed playlists tailored for community spaces such as cafés, bookstores, and cultural hubs. Ryan will also co-host four podcast episodes with ‘Mr. Wonderful’ on JazzFM, diving into the genre’s roots and tracing its diasporic journey.
The project aims to uncover Calypso’s hidden Canadian stories. While the genre is often celebrated in its Caribbean birthplace, few realize that the music has left a lasting imprint here in Canada — from the global stage of Expo ‘67 to the creation of Caribana, where Calypso became the soundtrack of a new cultural era.
In 2002, the Trinbago Unified Calypsonians Organisation (TUCO) declared October as Calypso History Month, a celebration that has since taken root across the Caribbean diaspora, including here in Canada. Calypso in the Air carries this legacy forward with a distinctly diasporic lens, linking four cultural hubs — Toronto, Montreal, New York, and London. Together, these threads form a living tapestry of sound and story, amplifying Caribbean voices worldwide and affirming that Calypso’s rhythm and resistance are not only preserved but continually reimagined, traveling across borders to inspire new generations.
For media inquiries and requests, please contact:
Natassia Morris, campaign lead
Natassia Morris Communications + Creatives Services
647-901-5457
natassia.s.morris@gmail.com
KAISO CITY PODCAST
KAISO CITY PODCAST
Step into Kaiso City this October for a special Calypso History Month broadcast on JazzFM91, hosted by Mr. Wonderful. Every week, journey through the vibrant, diasporic story of Calypso, from the Chantwells of Trinidad to its early recordings in New York, London, Montreal, and Toronto. Discover the deep connection between Calypso and jazz, two art forms rooted in improvisation, storytelling, and rhythm. In Kaiso City, we celebrate the legends and legacy of Calypso music with infectious rhythms and powerful storytelling, bringing the heartbeat of Afro-Caribbean culture to Toronto’s airwaves.
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