PART 4 CLOSING & AWARDS
Passing on the Rhythm
9:00PM-11:30PM | Dundas West Studio
✦ Bomber’s Dream by Jesse Ryan
✦ Iconography: Jit Samaroo by Mikhail Gibbings




9:00PM-11:30PM | Dundas West Studio
✦ Bomber’s Dream by Jesse Ryan
✦ Iconography: Jit Samaroo by Mikhail Gibbings
This screening section begins with the Awards at 9pm.
Every generation inherits a rhythm—and with it, the responsibility to carry it forward. Closing the festival are two inspiring portraits of musical visionaries whose artistry transformed Caribbean culture and continues to resonate across generations. Through the enduring legacies of The Mighty Bomber and Dr. Jit Samaroo, these films celebrate music not simply as performance, but as memory, mentorship, and cultural inheritance. As new artists embrace these traditions and make them their own, they remind us that the rhythm of the Caribbean is never static. It lives on because each generation chooses to learn it, honour it, and pass it on.
Directed by Jesse Ryan, Canada, 2026
Logline: When a grandson retraces the extraordinary journey of his grandfather, Calypso icon Clifton “The Mighty Bomber” Ryan, he discovers how Calypso shaped Black diasporic memory—and embraces his role in preserving its legacy for future generations.
Synopsis: Bomber’s Dream: The Music of the Mighty Bomber explores the life and enduring legacy of Clifton “The Mighty Bomber” Ryan, a Calypso King whose music shaped political and cultural consciousness across the diaspora. Filmed in Trinidad and Toronto, the documentary follows his grandson Jesse Ryan and the Kaiso StreetCollective as they create a new album inspired by Bomber’s work. Through rehearsals, archival footage, interviews, and performances, the film reframes calypso as a Black diasporic art form rooted in resistance, satire, and collective memory. Following Bomber’s passing in 2022, the film becomes both tribute and urgent reflection on cultural preservation and inheritance.
Runtime: 28m 10s
Directed by Mikhail Gibbings, Trinidad and Tobago, 2025
Logline: Iconography: Jit Samaroo follows the life and musical journey of legendary steelpan arranger and composer, Dr. Jit Samaroo. It is the third episode in the Iconography docu-series.
Runtime: 1hr 32m