Rupert Bent II, Jamaican Musician, Engineer and Pilot, Dies at 83
A Jamaican legend whose guitar, microphone, and cockpit coalesced into a lifetime of sound and flight has passed away.
Rupert Bent II died in Kingston on Monday, June 22 2026, at the age of 83. The death was confirmed by his wife of 27 years, Cindy Breakespeare, a former Miss World and long‑time figure in Jamaican cultural life. Bent’s passing comes a year after the death of his son, Rupert Bent III, a guitarist who worked with the band Third World, and marks the loss of two generations of musicians who were active in the island’s music scene.
Bent’s career began in the 1960s. In 1967 he played guitar on “Lips of Wine,” the debut single of 10‑year‑old Dennis Brown, produced by Derrick Harriott. The session places Bent at the origin of one of reggae’s most beloved careers. Over the following decades he worked as a session guitarist in studios across the Caribbean, and he was a member of Byron Lee and the Dragonaires for several years. The band was one of the most in‑demand live groups in Caribbean music history, and Bent’s work with them brought him to stages and studios throughout the region’s golden era.
In Kingston Bent served as chief engineer at the Jamaica Broadcasting Corporation while continuing to play guitar. His dual roles as engineer and musician were complemented by a third career: aviation. Bent joined Air Jamaica in 1973 and flew commercially for many years. In 1988 he relocated to Canada, where he continued working as an airline pilot. The fact that he maintained a professional aviation career alongside respected positions in music production and engineering is described by Breakespeare as “very easy‑going, very high‑focused and very humble.”
Bent’s educational background helped shape his multidisciplinary career. He was born in Westmoreland and raised partly in Portland. He attended Calabar High School and later the University of Technology in Jamaica. He also studied at Algonquin College of Arts and Technology in Ottawa, Canada, giving him a trans‑Atlantic academic foundation that influenced the range of work he would go on to do.
Family ties to music ran deep. Bent’s daughter Jana recorded several singles during the 1990s, and his granddaughter Salah is also a musician. The loss of both father and son within twelve months has left the reggae and wider Jamaican music community still processing the impact of two Rupert Bents who were not household names outside the industry but were respected within it.
The Jamaican music community has expressed its grief publicly. Breakespeare described Bent as a man who “loved his flying, music and engineering.” Her tribute highlights the breadth of his professional life, noting that each of those pursuits could have been a career on its own.
At present, Bent is survived by his wife, daughter, and granddaughter. No further public statements have been released regarding arrangements or memorials.
The passing of Rupert Bent II underscores the often‑overlooked fact that many key figures in Jamaican music history have held multiple professional roles. His life illustrates how technical skill, musical talent, and disciplined work ethic can intersect across seemingly unrelated fields.
