On January 5, 1947, Winston “Delano” Stewart was born in Kingston, Jamaica. He achieved significant success performing with The Gaylads in the 1960s before embarking on a solo career.

Stewart’s career began in his teens, recording ska tracks with Harris “B.B.” Seaton for the legendary music producer, Coxsone Dodd, at the famous Studio One. It’s often referred to as the “Motown of Jamaica,” and one of the island’s most celebrated record labels and recording studios.

He first performed with Seaton as the Winston & Bibby duo. They eventually became members of the Gaylads, one of the leading vocal groups in the rocksteady genre in Jamaica that was extremely popular from 1963-1973. The original group was comprised of Seaton, Maurice Roberts, and Stewart. The singer kept a lower profile than his partners in harmony and was often overlooked among the more ostentatious members of the group.

The trio survived for 10 years with multiple line-up changes before eventually dissolving. Stewart made the decision to leave the group in the 1960s and begin a solo career. He’d released some singles prior to leaving and recorded under producer Sonia Pottinger as a solo artist. He left Jamaica and moved to the U.S. in 1969.

In 1970, an album of his works recorded under Pottinger was released and in 2001, a compilation of his solo work was also released. He joined Seaton in 1991 for a concert honoring the history of Studio One. UB40 recorded one of Stewart’s biggest hits, “Stay a Little Bit Longer,” on their “Labour of Love II” album.

During his career, Stewart created a body of work that included 34 singles and EPs, along with two albums. The rocksteady and reggae vocalist left the music industry to pursue other interests after moving to the U.S.