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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). In November 1494, when the Medici were banished, he supported them. Soon afterwards he was rewarded with the protection of Julius II and many honours at the Roman court. In 1513 his arduous efforts on behalf of his lifelong patron secured the election of Giovanni dei Medici to the pontifical throne. Leo X repaid such services by presenting him with a purple robe, appointing him 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). Later on, the cardinal's strong sympathies for France lost him Leo's confidence. 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. Raphael painted a number of works for him, including fairly erotic frescoes for his bathroom in the Vatican.
His literary fame is mainly connected with the first comedy of note written in Italian prose, La Calandra (also, known as Il Calandro and La Calandria), was probably given for the first time at Urbino, about 1507. It was performed elaborately at Rome, seven years later, in the presence of Leo X and Isabella Gonzaga d'Este, Marchioness of Mantua. 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.
The main character, Calandro or Calandrino, was borrowed from Giovanni Boccaccio's Decameron in which he appears as a character in four stories. The author of the comedy sympathizes with Fulvia, and her lover Lidio, mocking the foolish husband of Calandro, who falls in love with Lidio, who changes into women's dress. The speeches of Fesenio, the servant of Calandro, shine with Italian sparkling jokes.
A Paduan poet serving at the Dresden Court, Stefano Benedetto Pallavicini, wrote a libretto based on the same story for the comic opera Calandro by Giovanni Alberto Ristori. It was first staged in 1726 at the castle of Pilnitz near Dresden, and in 1731 in Moscow it was the first ever opera performed in Russia.
There were also the operas by:
- Antonio Sacchini, L'avaro deluso, o Don Calandrino (24 November 1778 London)
- Johann Georg Schürer, Calandro (20 January 1748 Dresden)
- Giuseppe Gazzaniga, Il Calandrino (1771 Venice)
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