Each in his own way, Angelo Roncalli and Karol Wojtyla brought this joyful outlook to the demanding role of “servant of the servants of God.” Both men were outstanding spiritual leaders and major players on the world stage—the only two popes ever to be chosen “Man of the Year” by TIME magazine. Yet they made their gift of self with humor, wit, and even playfulness. (“I see that in the past you have given this honor . . . also to Stalin and Hitler,” John Paul teased TIME.)

Seeing the Funny Side. Both popes liked a good laugh. In fact, John XXIII will likely become the patron saint of stand-up comedians. Some of his one-liners are legendary. “How many people work at the Vatican?” a reporter asked him. “Oh, no more than half of them,” John replied with a wink.

On another occasion, a Curia official told Pope John that it would be “absolutely impossible” to open the Second Vatican Council by 1963. “Fine, we’ll open it in 1962,” John answered. And they did.

Then there was the time Pope John visited the Hospital of the Holy Spirit. All in a flutter, the religious sister in charge introduced herself, “Most Holy Father, I am the superior of the Holy Spirit!” To which John replied, “Well, I must say you’re lucky. I’m only the Vicar of Christ!”

With perhaps less hilarity but just as much quick wit, John Paul II also showed a talent for humorous remarks. To keep fit amid the demands and stresses of the papacy, he had a small swimming pool put in at the papal summer residence. When some people questioned the expense, he answered, “A conclave would cost a lot more.”

An American bishop, recalling John Paul’s amazing memory for names and faces, told of returning to Rome after having put on weight since his previous visit. “Is your diocese growing?” the pope inquired. The hefty prelate assured him that it was indeed expanding. “So is the bishop,” said John Paul with a twinkle in his eye.

Free to Be Themselves. These popes defied pious stereotypes simply by being themselves in public. People saw John Paul II pray and teach, as popes are expected to do. But they also saw him bantering with crowds, belting out Polish songs and carols, and playing hide-and-seek with the children of workers at the papal villa. With his acting background, this pope was a master of visual humor. He twirled his cane like Charlie Chaplin, modeled U2 lead singer Bono’s trademark sunglasses, and impishly peered out at a crowd through invisible binoculars.

John Paul also broke with precedent in the way he related to people. One example was Vittoria Ianni, a Roman street cleaner’s daughter. Overhearing two nuns talk about the pope’s early years of poverty in Poland, she felt a sudden desire to have him perform her upcoming wedding. This is not something that popes generally do. But when John Paul visited the outdoor manger that the city street cleaners set up every Christmas, Vittoria stepped up and made her request. To everyone’s astonishment, the pope said yes.

She and Mario Maltese were married in the Vatican’s Pauline Chapel in February 1979. Twenty-five years later, the couple returned, with their three grown children, for a private audience with Pope John Paul. “Our whole marriage seemed to have received a special blessing,” Mario told a reporter.

John XXIII broke the mold in ways too numerous to count. Natural, outgoing, and spontaneous by nature, he loved inviting workmen, Swiss guards, and “ordinary people” to stop in for a glass of wine. Saverio Petrillo, who oversaw the residence at Castel Gandolfo, remembers how Pope John “disappeared every now and then.” He would slip off the grounds “without telling anyone and without an escort, walking around among the people.” He wasn’t above a prank, either. Many a prelate, strolling with John through the Vatican Gardens, found out the hard way that the pope had had the irrigation system rigged to shoot jets of water on the unsuspecting!

And surely it was mischief that inspired the following exchange, which took place at a banquet when Roncalli was apostolic nuncio to France. In the course of the meal, he offered an apple to his neighbor, a woman in a dramatically low-cut gown.

“Do take it, Madame, please do,” he urged in his typically genial way. “It was only after Eve ate the apple that she became aware of how little she had on.”

Humor and Humility. More often than not, though, Angelo Roncalli was the target of his own humor. He often laughed about his appearance—big ears, large nose, and round figure. One day after a session with a photographer, he told the stately archbishop Fulton Sheen: “From all eternity, God knew that I was going to be pope. He had eighty years to work on me. Why did he make me so ugly?”

Another time, he greeted an ascetic-looking visitor with a sigh and the comment: “We will both have to say a prayer to God, beseeching him to remove half my excess fat to give it to you!”

Besides serving as an aid to humility, the self-deprecating humor was John’s way of putting others at ease. Similarly, Pope John Paul joked about the physical difficulties he encountered as his health declined.

At the October 1994 synod, six months after his hip surgery, all eyes were on him as he slowly hobbled to his place. Looking up at the bishops, the pope dispelled the awkwardness with a quip: “Eppur’ si muove.” The quote was from Galileo, and it referred to the earth’s rotation around the sun. But John Paul was smiling at his own creeping pace: “And yet, it moves.”

The humility was authentic. It wasn’t just for show. These men thought neither too little nor too much of themselves. They walked in the knowledge of who they were before God: beloved, treasured children but also frail creatures in constant need of grace.

We All Need Mercy. In one of his talks, Scott Hahn tells about an American priest who was in Rome for a conference and group meeting with John Paul II. Shortly before the audience, the priest noticed a man begging on the steps of a church. He looked familiar. It turns out that the two men had gone to seminary in Rome years before and had been ordained priests together.

Deeply shaken by the encounter, the priest blurted out the story to the pope when he met him later that day. John Paul promised to pray for the beggar. Then he invited the two men to join him for his evening meal.

Near the end of supper, John Paul asked for a few minutes alone with the beggar. After it was all over, the beggar revealed what happened.

“As soon as you left, the pope clasped my hands and said, ‘Father, would you hear my confession?’”

“‘I’m a beggar,’ I said.”

“‘So am I. We are all beggars.’”

So the beggar-priest heard the pope’s confession. And then, dropping to his knees, he tearfully asked John Paul to hear his.

Pope John XXIII struck the same note on Christmas Day 1959, when he visited Rome’s Regina Coeli prison. He told inmates that he came as their brother—and confided that one of his relatives had served a sentence for poaching. John radiated so much goodness and sincerity that there was not a dry eye in the place by the time he finished speaking.

On another occasion, though, one prisoner refused to see him. Learning that the man had murdered his wife, John persuaded the guard to let him inside the inmate’s cell. Then he opened with these words: “You know, I’ve never been married. But if I had married, I might have killed my wife, too.”

As Pope John wrote in his journal, “I live by the mercy of Jesus, to whom I owe everything and from whom I expect everything.”

And both he and John Paul II might have added, “Because of this, I can smile!”

Louise Perrotta is a Word Among Us editor. Anecdotes not attributed in the story are from materials by Henri Fesquet, Marco Nese, Archbishop Fulton Sheen, Tad Szulc, Greg Tobin, and George Weigel.