Episode 255 | Jimmy October

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In this episode of The Corie Sheppard Podcast, Trinidadian artist and poet Jimmy October opens up about his creative evolution, the story behind New Calypso, and his new project Episode 3 — a four-track EP that moves from the high-energy “Bam Bam” to the reflective “Desires.” He explains how fashion became self-expression (“the three belts story”), why his sound blends Calypso roots with modern R&B and pop influences, and what it really took to walk away from a secure hospital job to tour and co-write “Magic” with Kes.

Jimmy shares the discipline and structure behind his artistry — from his cadet years to his 1-hour-45-minute daily gym routine — and reflects on the emotional toll of creative life, from tears on tour to gratitude for his mother’s sacrifices. He also revisits his early poetry days in the Free Speech Project and performing at Machel Monday, connecting the dots between spoken word and music, and making a powerful case for why culture must keep evolving to survive.

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