The Caribbean music community is in mourning this week following the passing of legendary Trinidadian soca artist Oscar Dennis Benjamin, professionally known as Oscar B, who died on a Sunday morning in June 2026 after a prolonged battle with illness. Fans across Belize – a nation where his upbeat tracks became a staple of annual national September celebrations – are among the thousands grieving the loss of a performer who built a decades-long bond with local audiences.
Oscar B first catapulted to international recognition as the lead vocalist for Byron Lee and the Dragonaires, a group widely regarded as one of the most influential soca and calypso acts in Caribbean history. It was during his tenure with the band that he first established his deep connection to Belize, joining the group for annual performances during the country’s September independence celebrations, quickly growing from a visiting performer to a familiar, fan-favorite figure.
After departing the Dragonaires to pursue a solo career, Oscar B refused to let his relationship with Belizean audiences fade. He continued to return to the country for regular tour dates, delivering high-energy live sets that drew sell-out crowds, and became just as famous for his iconic signature “butterfly” dance move as he was for his catchy, rhythm-driven tracks.
In a touching show of regional support just days before his death, Tobago’s Chief Secretary Farley Augustine announced during a budget debate in the Tobago House of Assembly that lawmakers had approved emergency funding to cover Oscar B’s ongoing medical costs. In his announcement, Augustine highlighted the underrecognized impact the singer had on Caribbean culture, noting, “We have Oscar B ordinarily singing at our functions and not realising his mark on the region and the globe.”
In the wake of his passing, heartfelt tributes have flooded social media and community spaces from both Tobago and Belize, with countless fans sharing intimate, personal memories of interactions with the star. One woman recalled celebrating her wedding anniversary on Caye Caulker when she and her husband encountered Oscar B at the famous Split beach spot. After asking for a photograph and mentioning their special occasion, she said the singer immediately serenaded the couple with an impromptu performance that made their day unforgettable.
Another fan shared the story of being pulled on stage at the Biltmore to dance the iconic butterfly alongside the performer, describing the moment as one of the most joyful experiences of her life. Other memories include a private performance at a friend’s 50th birthday party in 2018, and a 2017 encounter at a Belize City store where Oscar B signed a Trinidadian one-dollar bill for a fan as a personalized keepsake. For many, the legacy of Oscar B extends far beyond his music, living on in the small, kind moments he shared with fans across the Caribbean.