Rupert Bent II, session guitarist on Dennis Brown's first hit, dies at 83

Rupert Bent II, the session guitarist who played on Dennis Brown’s first hit, died in Kingston on Monday at 83. His death closes the book on a musician whose name may have sat below the marquee, but whose work helped launch one of reggae’s defining voices.

Bent’s place in the music comes into sharpest focus through Lips of Wine, the 1967 Derrick Harriott production he played on when Dennis Brown was just 10 years old. That single became Brown’s first hit and a starting point for a career that later made him one of reggae’s most revered singers. Bent was there at the origin, one of the players helping turn a child singer’s promise into a record that traveled.

His story stretched well beyond that session. Born in Westmoreland and raised in Portland, Bent attended Calabar High School and the College of Arts, Science and Technology, now the University of Technology, Jamaica. He also studied at the Eastern Ontario Institute of Technology in Ottawa. In Jamaica, he worked as chief engineer at the Jamaica Broadcasting Corporation, then flew commercially with Air Jamaica starting in 1973 before moving to Canada in 1988 and continuing as an airline pilot.

Bent also spent several years with Byron Lee and The Dragonaires, a band that sat at the center of Caribbean live music for generations. A 2004 profile described him as a bandleader, and a later album launch showed he was writing too, including Cindy’s Song, a tribute piece tied to Cindy Breakspeare. Breakspeare, Bent’s wife of 27 years, described him as easygoing, high-focused and humble, and said he was deeply committed to flying, music and engineering.

The family losses around Bent deepen the sense of a lineage under strain. He died one year after his son Rupert Bent III, the guitarist known for his work with Third World, died after a short battle with lung disease. His daughter Jana also recorded singles in the 1990s. Younger fans may know Dennis Brown’s rise, or hear the family name through Third World and Sean Paul’s early studio circle, but Bent’s death brings the quieter builder back into view, the man whose playing, arranging mind and work ethic helped hold part of Jamaican culture together.