The stormy-tempered Tromboncino was among the most gifted early composers of the frottola. More than 170 of such pieces are ascribed to him. As a teacher, his influence was great enough that 20 years after his death his students in Venice were still used as a measure of quality in singing. By the account of his own letters, he grew up in Verona. His first music teacher was probably his father, Bernardino Piffaro, who was a player in the municipal wind ensemble. By the age of 20, he was already working as a trombonist for Francesco Il Gonzaga in Mantua, where he played at various feasts and events as part of the Mantuan wind ensemble.
His fortunes thereafter rose about as rapidly as they could. Throughout the late '90s, especially, his name is frequently mentioned in Mantuan documents in contexts alluding in one way or another to his musical talents or the singularity of his character. These include many requests for music from him, praise of him between different parties, and several gifts of money. The latter came from Isabella d'Este who, by 1590, had made him part of her personal retinue, where he served as lutenist, composer, and tutor.
Although he seems to have been the favorite of d'Este and her husband, there is great evidence that he was of a stormy, combative disposition. Besides having to flee to Venice in 1595 over some kind of violent offense, in 1599 (a Gesualdo copycat?) he murdered his wife when he found her in illicit congress with a lover; he apparently suffered only the most minor consequence, if any, for his actions. Despite yet another flight in disgrace from Mantua in 1501, he didn't permanently leave the service of d'Este until 1505. He must have been an outstanding musician indeed to have been treated so leniently. In 1505, he is found working for Lucrezia Borgia in Ferrara, whom he probably served through 1510, when much of musical retinue was laid off due to the expenses incurred in the war the against Venice. He was then taken under the wing of Cardinal Ippolito I d'Este in Ferrara in 1511. Until 1518, his movements are uncertain, but in that year he rented a house in Venice where he established a music school for gentlewomen. Business was brisk enough to pull him out of debt and pay to have his second wife and children come join him there.
Around this time, just when things looked good, he made what was perhaps his greatest career mistake when he requested a binding patent on the printing of his music. It's not known if this was granted, but it seems it was, for the publication of his music ceases at this date. While it protected his immediate financial interests, it prevented the work from receiving wider circulation (many manuscripts in circulation were pirated) so that his innovative frottolas, the acknowledged best being composed at the time, dropped out of the musical conscience of Italy before he was even dead.