In a spectacular display of musical artistry and cultural celebration, De Bear emerged victorious at the Montserrat Calypso Finals 2025, capturing the coveted Calypso Monarch title with an impressive 889 points. The prestigious competition, a cornerstone of the island’s cultural festivities, showcased ten exceptional finalists who masterfully blended sharp social commentary, lyrical wit, and exceptional musical craftsmanship.
The event culminated in a thrilling points battle that saw Kenzie claim first runner-up position with 840 points, while Sylk secured second runner-up honors with 806 points. Maggie D narrowly missed the podium, finishing fourth with 799 points in what organizers described as one of the most competitive fields in recent memory.
Additional rankings revealed Yogi Laser and Bimshaw in fifth and sixth places with 742 and 740 points respectively, followed by Boxer (714 points) in seventh position. Dardo captured eighth place with 694 points, while Blessings finished ninth with 693 points—just a single point behind his closest competitor. Black Pearl completed the talented lineup in tenth position with 677 points.
The Calypso Finals continue to serve as both entertainment and social mirror, preserving Montserrat’s rich musical heritage while providing an essential platform for storytelling, satirical expression, and meaningful social reflection. Event organizers emphasized the exceptionally high standard of competition, noting that the narrow point margins demonstrated the remarkable depth of talent within Montserrat’s calypso community and the vibrant health of this traditional art form.