A prominent critic has compared the later music of Josquin Desprez to that of Igor Stravinsky—more austere, and more deeply concerned with rigorous structural devices. To the extent which Josquin's "later" music may be distinguished, the comparison seems apt. Much of his compositional output late in life (after retiring to his hometown of Condé) appears to be centered around the five- and six-voiced chansons, many of which derive their structure from strict canonic procedures, and their character from more transparent melodic constructions. Both features and more may be found in his five-voiced canonic chanson, Plaine de dueil.

The earliest surviving copy of Plaine de dueil is anonymous, though several later printed and manuscript collections call the chanson a work of Josquin, and the same early volume contains other music of his. It has been suggested (though without clear evidence) that its courtly French text could be a poem by Marguerite of Austria, the recipient of the lavish manuscript chansonnier that first transmits Josquin's musical setting. The rather gloomy text, spoken by a woman's voice, laments her bondage to the eternal pain of love. It follows the classic "fixed form" of the five-line Rondeau, which in a prior century implied a fixed musical form of refrains and repetition. Josquin's music, however, transcends the boundaries of the form.

Josquin's music opens with a desperate sparseness, as four voices imitate one another on but two notes, a rising minor third. The fifth and highest (female) voice, literally chained to follow the (male) tenor in a strict canon, begins to open up the harmonic language by introducing new pitches, and a richly sonorous texture unfolds across a wide harmonic field. The second phrase expands the palette further, as it transposes the main canonic melodies (with their minor third) up an aspirant fifth. Yet the upper vocal reaches cannot hold, and the composer writes a third phrase that compensates with a sharp melodic downturn, returning to the "home" pitches for a strong medial cadence. What would have been the refrain of the Rondeau ("I am constrained...") takes on greater melodic weight, with two more active phrases both built upon descending motives, a melodic fourth and a plangent half-step. Josquin nonetheless uses a remarkable economy of melodic material: many musicians have noticed how these apparently more active phrases also recapitulate the simpler melodies from the opening. Not only the canonic voices, but each note responds to the bondage of the text.

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