This article reconstructs Raffaele Viviani’s ties with some of the greatest representatives of 19th and 20th century Italian theater, dwelling in particular on his relationships with Scarpetta, Pirandello, and Eduardo and Peppino De Filippo. The tools for such an investigation are letters and theatrical reviews. In order to highlight Viviani’s relationship with the theatrical scene of his time and with the preceding dramaturgical tradition, the article illustrates Viviani’s close relationship with Luigi Pirandello. In the space of a 20-year period, Viviani performed and transposed into the Neapolitan dialect three of Pirandello’s plays: La patente (1924), Pensaci, Giacomino! (1933), and Bellavita (1943). The analysis of this relationship dwells not only on the novel and effective linguistic operation carried out by Viviani compared with the original texts (in the case of transpositions/rewritings), but also draws attention to the system of characters in Viviani’s theater that have a Pirandellian origin, such as Don Mario Augurio (from the play by the same name) and Giovanni Scardino ( Fuori l’autore). Moreover, the article examines Viviani’s interest in Eduardo Scarpetta; in 1940, Viviani staged Scarpetta’s indisputable masterpiece, Miseria e nobiltà. Finally, the article considers Viviani’s relationship with Eduardo and Peppino De Filippo. The unusual relationship Viviani had with Eduardo De Filippo, a kind of ‘relationship/non-relationship’ that had its basis in the different poetic choices of the two men, is analysed.