John Wilbye began his career as a Yeoman in the provincial household of Lady Kytson, both as a general house-servant and a musician in her employ. As such, he provided the household with courtly entertainment in the fashionable forms of the English madrigal and the lute song. Many of his pieces were published in two madrigal collections (1598 and 1609). Unfortunately for us, Wilbye apparently gave off composing as his position within the household improved to that of a land-owning gentleman. Yet within the brief group of his pieces that survive, his assimilation of the Italianate style then in English vogue is immediately evident. A madrigal such as his five-voiced Weep, weep, mine eyes (from the 1609 Second Set of Madrigals) can perfectly encapsulate Wilbye's various influences.

In both text and music for Weep, weep, mine eyes mingle the strong Italian heritage and some traits of native Elizabethan culture. The subject of the text is a dialogue between two lovers facing death—their Italianate names Flaminia and Leander, as well as their references to the afterlife as "Elysian plain," could come from Italian poetic fields such as the 1588 collection L'amoroso Ero. At the same time, one prominent scholar has suggested the actual text could be an excerpt from an English drama performed at the Kytsons' Hengrave Hall. Wilbye's music similarly grafts the passionate gestures of the late Italian madrigal upon moments of an English lutenist's light textures. The strong chordal opening "weep, weep" could suggest either, as could the rhetorical transposition of the same music upwards as the second line echoes and intensifies its melancholy sentiment. The first speaker's "thousand deaths" evokes from Wilbye such a myriad of contrapuntal repetition that the name of Flaminia is even lost in the texture. Both opening couplets contrast strongly, however, to the lady's answer in the second half. First, the composer sets her cry "Ay me, ah cruel fortune!" to a surprisingly clear, yet jarring homophonic texture (as Wilbye might have seen in the madrigals of Marenzio). Yet the piece's conclusion looks to a better future for the lovers as they might love again in the hereafter. For this bucolic vision, Wilbye turns to a simpler, lute-like texture, yet intensifies it in turn with two musical sequences; these particular repetitive phrases both evoke the music of Ferrabosco and suggest the never-ending joys the lovers foresee.

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