Born in Split (then PR Croatia, FPR Yugoslavia) and raised in Vela Luka on the island of Korčula, he emerged onto the music scene in the 1970s thanks to the popular Split Festival, one of several musical annual events which began in the former Yugoslavia and still is being held in Croatia today.
His speciality was music influenced by Dalmatian Folklore. 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.
