Portugal, on the western coast of the Iberian Peninsula, is a country where the condensation of nearly a thousand years of history has collected into the reservoir of their collective psychology. It could be said that Portugal was one of the first mediums through which European influence disseminated into the rest of the world. Saudade is a Portuguese word that attempts to represent a vast compression of nationalistic ideas and sentiments into a single expression. It is often considered to be a feeling unique to the Portuguese given its relation to their complex history. The age of discoveries and the circumnavigation of Africa, a failed constitutional monarchy followed by a failed First Republic, a fascist dictatorship that lasted 48 years, a military revolution in 1974, these are all major components of Portuguese history that affect Saudade. The word Saudade plays a major role in what is referred to as Portuguesidade or Portugueseness. Constructed into a movement by Portuguese writers and poets, the nationalistic themes within saudade were used by the fascist-leaning, authoritarian regime of António de Oliveira Salazar’s “New State” (1932-1974) as a means to perpetuate public complicity. The word, with its numerous meanings and definitions, evolved through the 20th century and remains relevant for the Portuguese identity of today. This paper explores the complexities of national identity by focusing on the evolution of the parallel between Saudade and Portugueseness through the 20th Century.