The Caribbean music fraternity is mourning the loss of one of its most beloved entertainers.

Celebrated Tobagonian soca icon Oscar B, born Oscar Dennis Benjamin, died on Sunday, June 28 after complications related to a stroke he suffered earlier in May. He was 57.

In a poignant twist, his passing came just hours before the Tobago Family & Friends Healing Concert, a benefit event organised at the Shaw Park Cultural Complex to help raise funds for his medical treatment. Instead of a fundraiser, the gathering became an emotional celebration of his life, with fellow musicians, friends and devoted fans paying tribute to a man whose music had soundtracked Caribbean carnivals and festivals for decades.

Oscar B leaves behind a legacy that stretches far beyond his native Tobago.

He first emerged as a promising vocalist with the Signal Hill Alumni Choir before rising to regional and international prominence as the charismatic lead singer of the legendary Byron Lee and the Dragonaires in Jamaica.

His infectious stage presence, booming vocals and boundless energy made him one of the band’s standout performers during an era when the group dominated stages across the Caribbean, North America and Europe.

Over a decades-long career, Oscar B became synonymous with the joyful spirit of soca, delivering crowd-pleasing anthems that remain staples at carnivals and fêtes throughout the region.

Among his most enduring hits are Soca Bogle and Soca Tatie, songs that helped define his career and cement his reputation as one of Tobago’s most influential musical ambassadors.

Whether performing before thousands at Carnival or electrifying audiences on international stages, Oscar B possessed a rare ability to unite people through rhythm, celebration and unmistakable Caribbean energy.

His death marks the end of an era for Tobagonian music and leaves a void in the wider Caribbean entertainment landscape.

Though his voice has been silenced, the music that made generations dance will continue to echo through festivals, sound systems and Carnival celebrations for years to come.

Oscar B is survived by his family, friends and countless fans across the Caribbean and the diaspora, who will remember him not only as a gifted performer but as one of the enduring voices of soca music.