This dissertation is a selection and translation of the poetry of Sandro Penna (1906 Perugia – 1977 Rome), an important figure in Italian twentieth-century literature who remains largely unknown to English-language readers. Penna’s poems are brief but complete, desirous but self-possessed, traditional but transgressive. In his lifetime, Penna was infamous but intensely private, well-known in Italian literary circles but a non-participant in most aspects of literary and social life. In 1970, Pier Paolo Pasolini named Penna “perhaps the greatest and happiest Italian poet alive,” while the same year Amelia Rosselli described Penna’s behaviour as “a social suicide”. While Penna has for decades been considered a marginal figure in twentieth-century poetry, Italian criticism has recently begun to re-evaluate his place in the expanding modern canon. English translation, however, has not kept up, a trend that this dissertation corrects. One of the major contributions of this translation is its improved rendering of the rhyme, metre and other formal qualities of Penna’s verse, neglected in previous book-length translations, none of which are currently in print. This dissertation also includes a discussion of Penna’s biography, a review of the critical issues in his work, a history of Penna’s translation into English, and a description of the translation process used in this dissertation.