Jimmy Cliff
Jimmy Cliff got his big break during the ska era in the early 60s and managed to stay relevant through Jamaica’s rapidly changing musical periods of rocksteady and reggae until his international break came through his starring role as the rude boy, Ivan, in Jamaica’s first major motion picture, The Harder They Come. Since then he’s been deemed a major icon and has had a career that’s spanned over 50 years as a recording and major touring artist. —Dave Susser