The article is a survey of a number of aspects of the cantigas (Ladino lyric songs) repertoire of the Sephardi communities in the Ottoman Empire at the dawn of the modern era. The genre of cantigas is the dominant genre in the repertoire of the Ladino song, as well as the most dynamic and changing one. Many of the cantigas sung in the twentieth century are new compositions that spread throughout the Sephardi communities and entered the oral tradition in relatively short time. The cantigas reflect the events and changes of the time, in their contents as well as in their music, combining original compositions side by side with borrowings from neighbouring cultures. Commercial recordings and waves of immigration carried songs to new countries and new communities. Newly composed songs entered the oral tradition while their authors were often forgotten. The dawn of the twentieth century was the beginning of decades of poetic and musical creativity that came to an end with the outbreak of the Second World War.