Bomber’s Dream: The Music of The Mighty Bomber

Led by JUNO nominated, Trinidadian-born saxophonist Jesse Ryan, grandson of the late calypso veteran Clifton Ryan “The Mighty Bomber,” this special event marks the release of both the album and short documentary Bomber’s Dream: The Music of The Mighty Bomber. The evening begins with the premiere screening of Bomber’s Dream, an expository short docu-film exploring the life, work and cultural impact of The Mighty Bomber – calypso king, cultural ambassador and social commentator. Filmed across Trinidad and Toronto, the documentary weaves Bomber’s story with the contemporary creation of a new album by the Kaiso Street Collective, led by Jesse Ryan. Through rehearsals, studio sessions, archival footage and interviews with family members, artists and cultural leaders, the film reframes calypso not simply as party music, but as a Black diasporic art form rooted in resistance, social critique and collective memory. It traces how Bomber’s legacy, and calypso itself, helped shape cultural life in Trinidad, Canada and the United States during the civil rights era, and how the music continues to be preserved and reimagined across the diaspora today. Following the screening, audiences are invited into a panel discussion reflecting on Bomber’s legacy, the significance of calypso history and the importance of cultural preservation. The night concludes with a live concert performance by the Kaiso Street Collective, presenting fresh arrangements of music from the golden age of calypso, reimagined through the lens of modern jazz. The album features the music of Clifton Ryan and one of his mentors and greatest influences, Theophilus Philip, The Mighty Spoiler. The Collective features an exceptional ensemble of artists: Andrew Marzotto (guitar), Ewen Farncombe (piano), Michael Davidson (vibraphone), Roberto Occhipinti (bass), Anthony Daniel (drums), Alexander Brown (trumpet), Kelsey Grant (trombone), Jeff La Rochelle (tenor saxophone/clarinet), with Jesse Ryan as music director on alto and soprano saxophones. At its core, Bomber’s Dream is an intergenerational tribute and a call to action, asking who will carry these stories forward, and why preserving them remains urgent.