De Bear has been crowned Calypso Monarch at the Montserrat Calypso Finals 2025, securing the title with a commanding total of 889 points.
The competition, one of the highlights of Montserrat’s annual cultural calendar, brought together ten finalists who delivered performances blending social commentary, wit and musical craftsmanship.
Kenzie finished as first runner-up with 840 points, while Sylk claimed second runner-up honours after scoring 806 points. Maggie D placed fourth with 799 points, narrowly missing out on the top three.
Yogi Laser and Bimshaw followed in fifth and sixth places, earning 742 and 740 points respectively. Boxer placed seventh with 714 points, while Dardo secured eighth place on 694 points.
Blessings finished ninth with 693 points, just one point behind Dardo, and Black Pearl rounded out the field in tenth place with a total of 677 points.
The Calypso Finals continue to be a central feature of Montserrat’s cultural celebrations, showcasing the island’s musical heritage and the role of calypso as a platform for storytelling, satire and social reflection.
Organisers described the standard of competition as high, with close scoring across the field highlighting the depth of talent within Montserrat’s calypso fraternity.
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