Muzilog Remembers Oscar B: A Voice That Defined Tobago's Musical Spirit

It is with profound sadness that we join the Caribbean music community in mourning the passing of Oscar Dennis Benjamin, affectionately known worldwide as Oscar B, one of Tobago's most beloved entertainers and cultural ambassadors.

Our heartfelt condolences go out to his family, friends, fellow musicians, and the countless fans whose lives were touched by his remarkable talent and generous spirit.

Born in Signal Hill, Tobago, Oscar B discovered his love for music at an early age while singing in the Scarborough Methodist Church choir. His professional career began in 1982 with the Signal Hill Alumni Choir before he moved to Trinidad, where his commanding stage presence earned him a position with the renowned brass band Blue Ventures.

His career reached international heights in 1991 when, following an outstanding performance at a local Brass Festival, he was invited by musical director Neville Hinds to join the legendary Byron Lee & The Dragonaires. As one of the band's principal vocalists, Oscar B proudly represented Trinidad and Tobago on stages around the world while helping to bridge the musical cultures of Jamaica and the twin-island republic. His performances on classics such as "Soca Butterfly" and "Soca Tatie" helped define an era and contributed to the growth of Ragga Soca throughout the Caribbean.

Returning home after years of international success, Oscar B remained deeply committed to live music. Whether fronting the Gayatones, leading Karybbean Vybz, or performing with Oscar B and Vibes, he continued to champion authentic musicianship and inspire new generations of performers. His versatility, professionalism, and unwavering passion earned him the respect of audiences and fellow artists alike.

Those who knew Oscar B often speak not only of his extraordinary voice but of his humility. Despite his accomplishments, he remained approachable, kind, and deeply connected to his Tobagonian roots. He possessed the rare ability to make every audience feel like family, leaving behind memories that will endure for generations.

As we prepare this week's Neo Kaiso Heat Chart, there is an added poignancy in seeing Oscar B's latest release, "Crazy D Place," at No. 2. While the chart reflects the music our listeners embraced throughout the week, it also stands as a fitting reminder that great artists continue to speak through their work long after the final curtain falls.

We also acknowledge the announcement from the Tobago Updates Television family that the upcoming concert at the Shaw Park Complex will proceed as scheduled and will now serve as a tribute celebrating Oscar B's life, legacy, and immeasurable contributions to Caribbean culture.

Today, the music feels a little quieter, but Oscar B's voice will continue to resonate through every stage he graced, every song he recorded, and every heart he touched.

From all of us at Muzilog, thank you, Oscar B, for the music, the memories, and the legacy.

Rest in eternal peace. Your song lives on.

Tobago Updates. (2026). Facebook.com. https://www.facebook.com/share/p/1HHySdjuX2/