Pietro Aretino and Titian were compari. Titian designed author portraits for Pietro, five known painted portraits and two in narrative paintings. All were done in particular situations with intentions varying greatly in purpose and complexity. This study reconstructs these contexts as fully as possible, showing how they determine the concept of each portrait and enhance appreciation of Titian's artistry in revealing different aspects of Aretino's personality and character. After considering the author portraits, the study examines their relationship with Alfonso d' Avalos, who is featured with Aretino in both istorie, The Allocution and the Ecce Homo, in which Pietro appears as Pilate defending Christ. The earliest surviving independent portrait, 1538, represents Aretino as a divinely inspired writer. The 1545 portrait, conceived as one of a pair commemorating his condottiero friend Giovanni de' Medici, has the most complicated context. It was delayed by loss of Giovani's death mask, Titian's failure to do Giovanni's portrait, and further when Pietro's portrait was hidden from the recipient Cosimo I de' Medici. The study concludes with an assessment of their friendship