This chapter focuses on musical interpretations of Giambattista Marino’s (1569–1625) pastoral poetry in Monteverdi’s Sixth Book of madrigals from 1614. The pastoral mode gave Monteverdi licence to create imaginary worlds of musical shepherds and nymphs, just as it had given Marino the opportunity to create a web of poetic references reaching back to antiquity. The formal and stylistic experiments found in the pastoral madrigals, or the rime boscherecce, provided Monteverdi fertile ground from which to use musical materials in a similar way. The affinities and, in many cases, the incongruities between the pastoral images and characters in the texts and Monteverdi’s manipulation of them in music created a new kind of listening experience for the audience. It invited them to delight in the unexpected.