This article examines problems and difficulties regarding the translation of wordplays from German into Italian. Although wordplays have often been seen as quite impossible to be translated, this paper aims to consider the concrete translation strategies and techniques generally used to face the problem in concrete situations. In particular it focuses on the translation of wordplays in philosophical texts referring to concrete examples taken from some essays written by Walter Benjamin; in fact, in these texts, wordplays are not only used as rethoric or stylistic devices, but they convey an interesting expressive device that in many cases help to create the core of the philosophical development itself. (see. Hausmann, 1974; Käge, 1980; Tęcza, 1997).