One of the most interesting Popes in Catholic history was Pope Benedict IX who headed the Roman Catholic church between 1032 and 1048. Benedict IX was born in Rome as Theophylactus of Tusculum and had the rather unique opportunity to serve as Pope three times in the years between 1032 and 1048. Keeping in mind the philosophy of papal infallibility, this man has the distinction of being the only man to have sold the papacy, being the youngest pope, being the only man to have served as pope three times, being the first homosexual pope and being the first verifiable resigning pope.
Benedict IX was the nephew of his two immediate predecessors, John XIX and Benedict VIII. According to the Original Catholic Encyclopedia, Benedict had the papacy placed on him (i.e. given to him) by his father Alberic III when he was twenty years of age, in October 1032. He took the position with very few qualifications other than that he had connections with one of Rome's most powerful families. Apparently, little is known of most of his pontifical acts during his tenure, however, his "dissolute life" caused one faction of Rome to drive him out of his position as Pope in 1044. He was replaced by the antipope Sylvester III in 1045 who was, in turn, expelled by Benedict IX in the same year. Benedict IX resigned his office after it was suggested that he might marry and sold the papacy to Archpriest John Gratian (Pope Gregory VI) in May 1045, Benedict's godfather. Apparently, the bribe that John Gratian paid for the privilege completely bankrupted the church treasury, leaving it unable to pay its bills for months afterwards. Having second thoughts about selling the papacy, Benedict attempted to depose Gregory VI, causing King Henry the Third to intervene, largely because it was felt that the Italians could not been trusted to appoint a new pope that was free of corruption. In 1046, all three Popes, Benedict, Sylvester and Gregory, were booted from office (actually, Gregory stepped down, being the second pope to resign, Sylvester was dismissed and Benedict was coerced into resigning) and were replaced by a German Bishop Suidger who became Pope Clement II. In his first act as Pope, Clement II crowned King Henry III as the Holy Roman Emperor, a title sought after by Henry III and why he agreed to name Clement II as pope in the first place. In November 1047, Benedict IX again seized the papal office but was driven out in July 1048 to make way for another German pope, Damascus II, in November 1048.
Here's how some of his fellow Catholics described him:
A cardinal, Saint Peter Damian, described Benedict IX as "feasting on immorality" and "a demon from hell in the disguise of a priest".
Bishop Benno of Piacenza accused him of "many vile adulteries and murders".
Pope Victor III (1086 to 1087) referred to Benedict's "rapes, murders and other unspeakable acts. His life as a pope was so vile, so foul, so execrable, that I shudder to think of it." in his Third Book of Dialogues.
He is said to have been the first gay pope, holding orgies in the Lateran Palace. He also reportedly sodomized animals, hosted frequent bisexual orgies and went so far as to curse God and toast the Devil at every meal.
It is believed that Benedict IX died in Italy between December 1055 and January 1056 at the age of 43. Apparently, he repented and turned from his sins as pontiff prior to his early demise.