This article examines the appropriation of the pair Don Quixote and Sancho Pansa by Jacek Kaczmarski and Francesco Guccini, two iconic late twentieth-century songwriters (each had more strings to his bow) who were fascinated by Cervantes’ novel. While, traditionally, Don Quixote is seen as the dominant character and Sancho the subordinate one, in Kaczmarski's and Guccini’s songs Sancho is placed on an equal footing the errant knight. This striking revaluation was in a way conditioned by the medium, the twentieth--century art song with its aspirations to be alive to the concerns of the time. For singers and songwriters committed to the cause of social justice, in tune with the prevailing egalitarian, leftist ways of thinking, it was only natural to deconstruct the master/servant nexus at the heart of Cervantes’ novel. However, as the political systems of their home countries differed widely, the social activism pursued by the Polish and that of the Italian author is hardly comparable. While Guccini’s texts resonate with themes of social justice, Kaczmarski builds more bridges to Cervantes (not least in the sphere of poetry) in his song cycle. Despite all their differences, the work of the Polish bard and of the Italian cantautore demonstrates that the mindset and the social realities of the twentieth century mindset made it impossible to bring back Don Quixote without allowing room to Sancho Pansa.