Though he spent most of his professional career as a church musician, from his beginnings as a singer in Antwerp to his forty-year tenure with the French Royal Chapel and as treasurer for St-Martin in Tours, Johannes Ockeghem also lived the life of a courtier. His chansons in the high Courtly tradition were well-respected by his contemporaries, and were often the subject of emulation, rearranging, and adaptation. One of his earliest chansons, at least in terms of datable manuscript copies, is the Bergerette Ma maistresse et ma plus grant amye. This piece was singled out for praise by one of the greatest fifteenth-century music theorists, Johannes Tinctoris, in the eighth chapter of his Liber der Arte Contrapuncti (1477). Strangely enough, it was only in the 1980s that musicologist David Fallows found and published a fragmentary new source, which had been used as a scrap of book-binding paper, containing an excerpt of the song confirming the attribution.

The text and music of the song are in the fixed refrain form known as Bergerette; the refrain which both begins and ends the poem contains five lines, and one stanza of 3+3+5 lines stands in between. The text, as common in the waning Medieval tradition, speaks of a woman perfect in all her qualities, but who causes the speaker—who is unable to enjoy her presence—to weep endlessly, and desire death. The form of the music follows the form of the text, with a triple-time refrain section (the music of which also serves the third part of the stanza) and a shift to a languorous duple-time after the first refrain. Its style, also in an archaic mode, is treble-dominated, with a clear melody voice above two angular supporting voices; the lower voices are without text. Several different versions of the song survive, in different transpositions, and even with some apparent recomposition. This song provided the basis for Ockeghem himself to compose the incomplete Missa Ma maistresse; the music of the Mass even provides another slightly emended version of the chanson.

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