John Dowland, though still exiled from England, was known by 1600 as a master of English secular song. His First Booke of Songes was being reprinted after only three years, concurrently with the Second Book's release. This second volume, dedicated to Lady Lucie Bedford in an acrostic poem, had a more troubled sales run; it again testified, however, to Dowland's unparalleled skill in setting English verse. The Second Book opens with songs of a simpler texture than those of the first, thinning to only a single voice and lute. Though composing thus on a smaller canvas, Dowland intensifies both the lyrical freedom and emotional intensity of his songs. Both freedom and intensity are immediately evident in the very first song, I saw my lady weep.

In the vocal melody of I saw my lady weep, Dowland's noted rhythmic freedom goes beyond any English composition to date. After the first two phrases, the melody virtually abandons the poem's formal structure in favor of its own supple, inner logic. The meter even dissolves temporarily in the final line of each stanza (with words such as mirth and love). Following the dominant textual image of tears whose grief ennobles the Beloved, the melody features frequent suspensions and downward motion; once (as the text mentions her perfect eyes) an affective B flat further intensifies the line. The accompanying harmonies, rich in suspensions and phrygian cadences, add further bite to the song's emotional content. The accompaniment's bass also contains numerous iterations of a descending melodic fourth, an unmistakeable sign to Dowland's audience of lamenting.

An extraordinary intertextuality deepens the composition's richness. I saw my lady weep was published immediately before Dowland's signature tune: Flow my tears. Musically, both songs inhabit the same key, both use the descending tetrachord; I saw my lady weep even concludes on a half-cadence that directly segues into Flow my tears. The link between the pieces becomes stronger later in Dowland's life, as he quotes from this very song in one of his instrumental Lachrymae, composed for the death of Queen Elizabeth. The song's text also carries close ties to several similar pieces: a madrigal of Alfonso Ferrabosco and a song of Thomas Morley (also from 1600) use similar texts, as does a well-known sonnet of Alessandro Lionardi. Finally, the printed song is dedicated to "the most famous, Antony Holborne"; the evocation of Holborne suggests that the weeping lady is, in fact, Dowland's own lovely art of music.

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