He received a substantial literary training, and became a preceptor and boon companion of Giovanni dei Medici, the future Pope Leo X (from 1513 to his death in 1521).

Leo continued to show his favor by appointing Bibbiena his treasurer and entrusting him with many important missions, among them the command of the Papal army in the War of Urbino (1517) and a legation to France (1518).

As cardinal he steadily extended his generous patronage of the arts - he was a close friend of Raphael, whom he had known since his youth, and arranged his engagement to his niece.

Though containing glaringly immoral scenes, using the plot of Plautus's Menaechmi, it possessed the features of modern comedy and won plaudits for its sparkling wit and fine characterization.

A Paduan poet serving at the Dresden Court, Stefano Benedetto Pallavicino, wrote a libretto based on the same story for the comic opera Calandro by Giovanni Alberto Ristori.