This painting unquestionably boasts of an illustrious provenance, borne out by, among other things, the literary sources. According to Viviani's biography, repeated in Fornasari's catalogue of Pietro Benvenuti's work, the Angelica and Medoro was "painted for a Sicilian duke in around 1800". There also exists a preparatory drawing for the picture (Fornasari 2004, fig. 123).

The picture translates into paint the extremely well-known passage in the Orlando Furioso that Ludovico Ariosto wrote in several stages and published for the first time for the D'Este court in Ferrara in 1516.

Canto XIX tells of the love between Angelica, Princess of Cathay, and the Saracen foot soldier Medoro. Medoro was seriously wounded in battle and lying seemingly lifeless on the ground when Angelica, enchanted by his good looks, revived him with medicinal herbs. The two became inseparable lovers and decided to wed.

They carved their names on a tree wherever they went, and that is the precise moment that Pietro Benvenuti has chosen to depict as the subject of his painting.

When Angelica decided that the time had come to return to Cathay and to rule her kingdom with Medoro, to thank a shepherd and his family for their hospitality, she made them a gift of the bracelet that Roland had given her as a token of his love, while she only considered it for its beauty and its value.

Roland, a Paladin of Charlemagne enamoured of the beautiful Angelica, happened to travel to the area. On seeing the two lovers' names carved on a tree and having his suspicions confirmed by discovering the bracelet that he had given Angelica in the shepherd's possession, he lost his mind.