An unassuming little three-voiced piece entitled Fortuna Desperata began appearing in music manuscripts towards the end of the fifteenth century; its simple yet jaunty counterpoint quickly became tremendously popular, being rearranged at least six times with up to three added voices, serving as the foundation for a number of keyboard and lute intabulations, and donating its second voice for the cantus firmus of several masses. The tune's origin remains unknown. Although an early source credits Antoine Busnois with the composition, Busnois is not known to have ever set an Italian text directly. It appears to be part of the (loose) vernacular genre of the frottola; its half-serious text has been roughly translated as "Desperate Fortune, unfair and cursed, who has denigrated the good name, of that chosen woman." At any rate, it proved fertile ground for adaptation to the cyclic mass, including settings by the eminent Josquin Desprez, and the "Orphic" Jacob Obrecht. Obrecht's mass on "Fortuna" seems to have been the first, with Josquin later paying homage to (and competing with) the Flemish master's. Its composition may even date from Obrecht's first Italian visit, to Ferrara, in 1487-1488.

For Obrecht, "Fortuna" offered both a cantus firmus melody useful for the structural planning of his mass on the large scale and also a tune with clear potential for local harmonic organization. The Mass thus neatly embodies the two central musical concerns of his mature style. Taking the tenor voice of the frottola as his structural voice, Obrecht apportions it to each of the five movements of the Mass Ordinary. All four voices get the cantus firmus at least once (tenor in Kyrie I; alto in Kyrie II; superius in Sanctus; bassus in Osanna, etc.). But the most fascinating manipulation comes in the Gloria and Credo, the cantus firmus of both being marked with the a canon stating, "In medio consistit virtus" ("Virtue lies in moderation," or more literally, "Virtue stands in the middle"). The resolution of this canon requires the singer to begin with the single pitch F, which "stands in the middle" of the line, and then read the music from the middle backwards to the beginning; after this, the lonely note in the middle is repeated, and the second half sung to the end. The Credo, a movement of exactly equal length, reverses the process: lonely note, second half end to middle, lonely note, first half beginning to middle. This convoluted plan wittily suggests the unpredictable movement of Fortune's Wheel. (Note that in Josquin's mass, the rhetorical coup comes in the Agnus Dei, when the bass sings Fortune's melody in inversion, literally upside down.) Obrecht also demonstrates in this Mass palpable control over local harmonic direction and cadences, one of the hallmarks of his mature style. One need listen no further than the opening of Kyrie I to see the well-paced progression of cadences, which build momentum until the final voice enters, culminating the snatches of the "Fortuna" melody in the cantus firmus statement. As early as the Mass might be, it already shows the composer's full compositional assurance.

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