His speciality was music influenced by DalmatianFolklore. His first domestic hit was called "Picaferaj" in 1967. Most of his early songs were written by popular songwriter Zdenko Runjić. One of the most famous was "Nadalina" which also featured actor Boris Dvornik, and the popular Dalmatian anthems "Galeb i ja" and "Skalinada".
Dragojević maintained his popularity in ensuing decades, while in the 1990s his songs became less influenced by domestic folk and more by global music trends. At that time he was often referenced as Croatia's oldest pop star. After his collaboration with Zdenko Runjić, he recorded several more albums that proved to be popular with his fan base. His New Year performances on Bana Jelačića Square in Zagreb are very famous.
Today, Oliver is still active on the Croatian music scene often recognized as one of the country's most popular singers and musicians.