We’re kicking off our Calypso 2026 journey with a song that will make you reminisce and smile: “Jockey Shorts.” It is a silly song but one that is playful and brings back memories of Sparrow's Obeah Wedding. This song is a cultural darling, wrapped in witty island slang. In the Caribbean, a man’s underwear is fondly called “jockey shorts,” and the comedy unfolds as Mr. Lee accuses Debra of stealing his shorts to cast a spell and keep him bound to her.
The melody flows sweetly, with Mr. Lee gliding effortlessly across the rhythm. Produced by Khadeem Edwards of Xklusiv Muzic Productions and Faraoh Black, this track proves that the heart and soul of Calypso are alive and thriving as Carnival 2026 approaches. And for lovers of authenticity: every beat is powered by live instruments, not computer-generated rhythms.
The collaboration shines—Khadeem Edwards and Brent Toussaint’s compositions, paired with Mr. Lee’s rich vocals, bring Tyro Matthews’ songwriting to life. The storytelling takes us back to a time when obeah and spell-casting were believed to hold sway over relationships, often more than traditional courtship. It’s cheeky, nostalgic, and irresistibly Caribbean.
The revelation is clear: Calypso is alive and well in Trinidad and Tobago. This music carries a vibe you can dance to, laugh with, and enjoy wholeheartedly. As our first modern calypso feature for 2026, “Jockey Shorts” sets the tone for what promises to be a vibrant season.
We look forward to hearing it at Calypso Fiesta 2026. Share this post, spread the joy, and keep coming back to Kaiso Dial for all the new calypsos.
From the Artist's YouTube Page
Calypso is where it all began—the roots, the rhythm, and the reason why we love this music. Jockey Shorts is his way of paying tribute to that timeless sound while keeping the fun and storytelling alive! Long live the CULTURE that gave birth to Soca!
Production Notes/Music Credits:
Song Title: Jockey Shorts
Artist/Performed by: Mr. Lee
Written by: Tyro Matthews
Produced by: Khadeem Edwards of Xklusiv Muzic Productions & Faraoh Black
Composed by: Khadeem Edwards & Brent Toussaint
Mixed & Mastered by: Xklusiv Muzic Productions™
Rhodes by Pastor Anthony Moses & Khadeem Edwards
Brass Arrangement by Khadeem Edwards & Kenny Phillips
Tenor Sax by: Oral Rodriguez
Trumpet by Roger Jaggasar
Trombone by: David Jacob
Background Vocals by: Kharissa Edwards, Khadeem Edwards & Tyro Matthews
Publishers/Copyright Control (COTT)/(BMI)/Songtrust, NY
Distributed by: FoxFuse LLC
Genre: Calypso 🎶
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We present the music here for your listening pleasure and promotional purposes only, adhering to the "Fair Use" Musical Content Copyright Disclaimer under Section 107 of the Copyright Act 1976. Kaiso Dial/Calypso Music Blog © 1990 by Santiwah is licensed under CC BY-SA 4.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-sa/4.0/.
♫Please click the music player button below to listen now (a small triangle in the Music player/TV frame).
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