The flowering of Italian musical composition in the age of Petrarch and Giotto was led by the three northern composers: Maestro Piero, Giovanni da Cascia, and Jacopo da Bologna. Jacopo, like the others, seems to have taken native vernacular traditions—in his case preeminently the madrigal—and codified a strong musical tradition about them. Jacopo's 34 surviving works comprise twenty-five madrigals for two voices, seven madrigals and cacce for three voices, a single lauda (the incomplete Nel mio parler di questa donn' eterna), and a Latin motet (Lux purpurata raddiis) in praise of his Milanese patron Luchino Visconti.

Some eclecticism of practice in his works may be due to his interest in music theory; Jacopo was one of the few composers of his time to leave theoretical writings in prose. It may also stem from his exposure to the music of the French Ars nova, as seen in his unique tritextual madrigal Aquil' altera, or in his fetching use of the technique of hocket to represent the cooing of a turtledove in Fenice fu'e vissi. Jacopo, Piero, and Giovanni da Cascia apparently participated in musical contests among themselves when residing together at the Veronese court, composing a madrigal cycle together, and setting a group of texts with similar hidden references to local figures in Milan and Verona. Throughout his life, he seems to have sought a suavity of melodic writing (which would stylistically help to pave the way for Francesco Landini and Bartolino da Padova).

In Jacopo's hands, the Italian Trecento madrigal evolved its classic form. Two or more tercets—the lines containing either seven or eleven syllables—are followed by a "Ritornello" in a contrasting meter; both voices carry this text. The most common procedure sets each line of text to a phrase consisting of a held consonance, followed by a flowering of long and rapid melismatic writing, a burst of syllabic declamation, and a final melismatic approach to the cadence. Examples of the balance between syllabic and melismatic music may be seen in Jacopo's In su bei fiori and Un bel sparver. In other madrigals, he experimented with closer motivic relationships between the two voices; this is the case in his famous contemporaneous setting of Petrarch's Non al suo amante, and more clearly in the similarly well-known Fenice fu'e vissi. Another frequent stylistic trait of Jacopo's (which would also resurface in the music of Landini) is a transition melody in a single voice which links two phrases, as seen in O cieco mondo.

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