Chaplin's debut albums were Red Pond and Chaplin Chant, both major successes in Jamaica. Que Dem, produced by George Phang was phenomenally popular, and was one of the most critically acclaimed albums of the time. His popularity declined sharply in the late 1980s and 1990s, though; he continued recording, working with legends like Bunny Roots, Josey Wales, Sly & Robbie, Junjo Wales, Roots Radics and Doctor Dread.