Aretino prospered, living from hand to mouth as a hanger-on in the literate circle of his patron, sharpening his satirical talents on the gossip of politics and the Papal Curia, and turning the coarse Roman pasquinade into a rapier weapon of satire, until his sixteen ribald Sonetti Lussuriosi (Lust Sonnets) written to accompany Giulio Romano's exquisitely beautiful but utterly pornographic series of drawings engraved by Marcantonio Raimondi under the title I Modi finally caused such outrage that he had to temporarily flee Rome.

After Leo's death in 1521, his patron was Cardinal Giulio de' Medici, whose competitors for the papal throne felt the sting of Aretino's scurrilous lash.

The election of his old Medici patron as Pope Clement VII sent him briefly back to Rome, but death threats and an attempted assassination from one of the victims of his pen, Bishop Giovanni Giberti, in July 1525,[10] set him wandering through northern Italy in the service of various noblemen, distinguished by his wit, audacity and brilliant and facile talents, until he settled permanently in 1527, in Venice, the anti-Papal city of Italy, "seat of all vices", Aretino noted with gusto.

While at court in Mantua he developed a crush on a young man called Bianchino, and annoyed Duke Federico with a request to plead with the boy on the writer's behalf.

[17] His literary talent, his clear and sparkling style, his varied observation of men and things, would have made him a considerable writer under any circumstances, destitute as he was of the power of conceiving a genuine work of art, such as a true dramatic comedy; and to the coarsest as well as the most refined malice he added a grotesque wit so brilliant that in some cases it does not fall short of that of Rabelais.Apart from both sacred and profane texts – a satire of high-flown Renaissance Neoplatonic dialogues is set in a brothel – and comedies such as La cortigiana and La talenta, Aretino is remembered above all for his letters, full of literary flattery that could turn to blackmail.

They circulated widely in manuscript and he collected them and published them at intervals winning as many enemies as it did fame, and earned him the dangerous nickname Ariosto gave him: flagello dei principi ("scourge of princes").

La cortigiana is a brilliant parody of Castiglione's Il Cortegiano, and features the adventures of a Sienese gentleman, Messer Maco, who travels to Rome to become a cardinal.

[22] Luba Freedman cites a fourth portrait, from "not later than 1535", but Xavier F. Salomon, chief curator at the Frick Collection, writes that "there is no evidence that it ever existed".

"Probably no other celebrity of the cinquecento had his image reproduced so often and in so many media: paintings, frescoes, sculptures, prints, medals [...] At various stages of his life Aretino was also portrayed by Sebastiano del Piombo, Alessandro Moretto, Francesco Salviati, Jacopo Tintoretto, and Giorgio Vasari.

His likeness was reproduced on medals by Leone Leoni, Francesco Segala, Alfonso Lombardi, and Alessandro Vittoria and his image was sculpted by Jacopo Sansovino and Danese Cattaneo.

His dialogues, La Nanna, Aretino wrote, "demonstrate the superiority of my reserve to your indiscretion, seeing that I, while handling themes lascivious and immodest, use language comely and decorous, speak in terms beyond reproach and inoffensive to chaste ears.

Bernadine Barnes writes that no sixteenth-century critic noticed "the portrait of Pietro Aretino in the fresco.... [V]iewers of our own time have often seen him as St Bartholomew, who brandishes a knife in one hand and holds the skin with the semblance of Michelangelo's face in the other.

"[32] Aretino is frequently mentioned in English works of the Elizabethan and later periods and differently appreciated, in comments ranging from "It was one of the wittiest knaves that ever God made" of Nashe (The Unfortunate Traveller) to "that notorious ribald of Arezzo" of Milton's Areopagitica.

[33] The English traveller Sir John Reresby visited "the obscene profane poet" Aretino's grave in the church of San Luca, Venice, in the mid-1650s.