Martyrdom is typically a real downer, but Saint Lawrence proved to have the last laugh when Pope Sixtus II sentenced him to death by way of roasting; while being burned on the rotisserie Lawrence turned to the executioners, and said, I'm cooked on that side, turn me over, and eat.
While it certainly helps to have a clean record if you want to become the moral and spiritual leader of the Roman Church, its not a requirement. Pope Boniface VI was elected pope even though he had twice been defrocked because of immoral activity.
Mass media have brought recent priest sex scandals into the limelight, but its actually been a problem in the church for hundreds of years. These Popes have all allegedly died while engaging in sexual conduct: John VII (murdered by enraged husband of the woman he was in bed with), John XIII (murdered by a jealous husband), Pope Paul II (heart attack while sodomizing a page boy).
While most popes have gone with safe choices when choosing their new pontiff name, there is only one set rule: they cannot choose Peter. Hypothetically, a pope can become Pope Jesus Christ, Pope God, or even Pope Innocent II (but not Pope Innocent I that name was already used).
Many people know that the reason priest cannot marry has more to do with property, and less to do with purity and devotion to God; what most people do not realize is there is a loophole around this clause. If a man becomes a Lutheran priest, marries, and later converts to Catholicism, he is eligible to become a Catholic priest and keep his wife.
The youngest person to ever lead the Catholic Church was only a teen. Pope John XII was 18 when he became pope.
The term devils advocate has Catholic origins. The term was coined by the church to describe the person appointed to give the opposing viewpoint when deciding if a person should be sainted.
Some popes have all the luck; they get several years of good health to leave a legacy. Others not so lucky. Pope Urban VII was elected pope September 15, 1590, and died September 27, 1590. He is most remembered for dying.