The paper addresses Tomás O’Crohan’s The Islandman (1929) as a representative of Irish native autobiography. The genre, it is argued, best defines the specificity of O’Crohan’s work, since it well delineates the complexity of its creation process involving an author, an editor, and a translator. Furthermore, the reading of The Islandman as Irish native autobiography sheds a new light on the text as capturing Walter Benjamin’s media shift from oral to written tradition observable at the beginning of the twentieth century. Tomás O’Crohan manages to converge the art of storytelling with a new genre of autobiography thanks to many foreign influences, especially Maxim Gorky’s life-narratives. Consequently, The Islandman, contrary to the traditional understanding of the work as purely Irish, thus free of any outside leverage, emerges as a cosmopolitan text which, similarly to other European literary works of the time, successfully adapts the oral heritage to a new form of autobiography.