28/06/2026
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π’π§ππ₯ ππ¨π° ποΈ
It is with profound sadness and heavy hearts that the Signal Hill family announces the passing of our beloved Oscar Benjamin, affectionately known to many as Oscar B.
Today, the music is a little quieter, the stage a little dimmer, and our hearts heavier.
Oscar B was more than a gifted singer and entertainer. He was a living legend, whose extraordinary talent carried him onto international stages as a performer with Jamaica's renowned Byron Lee and the Dragonaires. Yet, despite his remarkable achievements and acclaim, he remained the very definition of humility. His warm smile, gentle spirit, and genuine kindness made everyone feel seen, welcomed, and valued.
He possessed that rare ability to light up a room without demanding attention. Whether through song, laughter, or a simple conversation, Oscar left every place and every person better than he found them. He reminded us that true greatness is measured not only by talent, but by the love, respect, and joy we leave in the hearts of others.
To generations of the Signal Hill family and the wider Tobago community, Oscar B was an inspiration, a man who carried his gifts with grace and his success with quiet dignity. His voice may now be silent, but the melodies he shared, the memories he created, and the lives he touched will continue to echo for generations to come.
As we mourn this tremendous loss, we also celebrate a life that was beautifully lived, a life of music, service, friendship, and unwavering humility. To his family, friends, classmates, former colleagues, and all whose lives were enriched by his presence, we extend our deepest and most heartfelt condolences. May you find comfort in knowing that Oscar's legacy will never fade, for legends never truly die. They live on in every story told, every song remembered, and every heart they touched.
Rest peacefully, Oscar B. πΆποΈ
Your final performance may have ended on earth, but Heaven has welcomed another beautiful voice into its eternal choir.
Gone from our sight. Forever in our hearts. ππ
π πππ ππ§π πππ€ππ¬ ππ’π¬ π
π’π§ππ₯ ππ¨π° ποΈ
It is with profound sadness and heavy hearts that the Signal Hill family announces the passing of our beloved Oscar Benjamin (Class of 1985), affectionately known to many as Oscar B. Today, the music is a little quieter, the stage a little dimmer, and our hearts heavy.
Oscar B started singing with the Signal Hill Alumni choir under the tutelage of Mr. John Arnold. Oscar B was more than a gifted singer and entertainer. He was a living legend, whose extraordinary talent carried him onto international stages as a performer with Jamaica's renowned Byron Lee and the Dragonaires. Yet, despite his remarkable achievements and acclaim, he remained the very definition of humility. His warm smile, gentle spirit, and genuine kindness made everyone feel seen, welcomed, and valued.
He possessed that rare ability to light up a room without demanding attention. Whether through song, laughter, or a simple conversation, Oscar left every place and every person better than he found them. He reminded us that true greatness is measured not only by talent, but by the love, respect, and joy we leave in the hearts of others.
To generations of the Signal Hill family and the wider Tobago community, Oscar B was an inspiration, a man who carried his gifts with grace and his success with quiet dignity. His voice may now be silent, but the melodies he shared, the memories he created, and the lives he touched will continue to echo for generations to come.
As we mourn this tremendous loss, we also celebrate a life that was beautifully lived, a life of music, service, friendship, and unwavering humility. To his family, friends, classmates, former colleagues, and all whose lives were enriched by his presence, we extend our deepest and most heartfelt condolences. May you find comfort in knowing that Oscar's legacy will never fade, for legends never truly die. They live on in every story told, every song remembered, and every heart they touched. Rest peacefully, Oscar B. πΆποΈ
Your final performance may have ended on earth, but Heaven has welcomed another beautiful voice into its eternal choir.
Gone from our sight. Forever in our hearts. ππ
πΈ Mr. Dave Elliott
