My friend Tessa, who helped found the Institute, was recently looking for some stock photos of monks that we could use on our web sites. All she could find were scary images of dour fanatics. So, fifty years after my friend’s complaint, popular culture may still imagine monks and religious in general as scrupulous, prudish, priggish, superstitious, humorless.

Early in my monastic life I encountered St. Philip Neri through a biography written by Theodore Maynard. I also read some sermons about Neri written by the English priest (and detective fiction writer!) Ronald Knox. Philip sounded like a real “fool for Christ” (1Cor. 4:10) who managed to take most things, especially serious, pious and powerful people, with a grain of salt. As a convert to Catholicism, I was looking for role models. This seemed like a good place to start.

Laughter strikes me as a sign of faith, of trusting that, as Julian of Norwich believed, “all shall be well.” St. Teresa of Avila said, “Lord, deliver me from sour-faced saints!” You have probably met someone who has suffered a lot, witnessed horrors, and somehow manages to walk in beauty and contagious joy. It’s a wonder to me. It shows up in the 1997 World War II movie “Life is Beautiful,” starring Roberto Benigni as Guido, who tries to protect his son from the truth-lie of their death camp existence. I like to imagine the disciples and Jesus laughing after Easter as it starts to soak in that he really is alive. The last laugh.

For those of us who celebrate Halloween as the eve of the Feast of All Saints, it makes sense to laugh in the face of death. We can pretend that at least someday, death will lose its sting for us. So here in the Southwest, we see skeletons dressed to the nines, strumming guitars and dancing for joy, as in the movie Coco. That’s a long-winded way to introduce a pretty weird and funny saint.

Philip Neri was born in Florence in 1515, the same year as St. Teresa of Avila. In fact, Philip, Teresa, and Ignatius, the Basque founder of the Society of Jesus (Jesuits), were all canonized on the same day in 1622. In Philip’s patriotic Rome, the locals allegedly proclaimed that “today the Pope canonized two Spaniards and a Saint.”

At an early age Philip knew what he didn’t want to be: a businessman. But he knew he loved God, and as a young man he drifted to Rome, where he lived as a “street hermit.” He prayed in various churches, occasionally preached, visited the sick and helped nurse them. He had a knack for finding food for the destitute. He found a little room and tutored the landlord’s son in exchange for rent.

He was affable, but also solitary. His confessor basically pressured Philip to be ordained since the church was keen on centralizing its power at that time. It did not nurture freelance ministers. Not only did he agree to priesthood, but clerics told him to found a community and Philip caved. He was totally unambitious when it came to the institutional church. Several powerful men in the Vatican had become priests because Philip inspired them. So they kept trying to make him a cardinal to show their appreciation. The Pope sent Philip a special red hat, a biretta, worn only by cardinals. Philip, the story goes, enjoyed using it as a soccer ball.

Philip strikes me as a free man. He despised no person but hated pride and greed. He was happily solitary and happily engaged with friends. He didn’t mind if a friend interrupted his prayer. He said he was simply going from God to God.

Christianity has tended to depict saints as “supernatural,” which often strikes me as un-natural. But Philip seems so natural. And a little screwy, in a good way. He could relate to anyone. One of his best friends was an illiterate monk, and another was a stern aristocrat and bishop: St. Charles Borromeo. He had no qualms about writing the pope, whom he knew when the pope was a baby, to complain that His Holiness never came to visit. He stood up against officials who sentenced the unemployed poor and Romanis to enslavement in the galleys.

“He prayed and trembled and wept,” Maynard writes, “he read comic books and went into ecstasies.” He even read comics sometimes during mass in order to prevent going into ecstasy, which he considered tacky. When young friends were sad, “he boxed their ears to make them cheerful; he made jokes and told men their sins before they confessed them; but there were few who could resist the charm of Philip’s personality and the vehemence of his prayers combined.”

He could walk up to you and ask, “When are we going to start loving God?” and you would probably not feel embarrassed. I think it felt like someone suggesting we take off together for the swimming pool or a pub. Now? Sure! Sounds delightful.

Philip fought pride with humor. Traditionally, asceticism was prescribed to combat pride. For example, you do difficult tasks such as fasting or making reparation for harm done or giving alms to break the power of selfishness. You mortify your appetites and are humbled by the power they have. But of course, then you get proud of your self-control and charity. One old form of asceticism involved wearing a “hair shirt,” often a goat skin undershirt, to cause discomfort and combat lust. When a penitent asked Philip for permission to wear one, Philip gave it, with one condition: “Wear it outside your fashionable coat.”

Whereas his contemporary St. Ignatius of Loyola, founder of the Jesuits, developed a clear method of prayer, the revered Spiritual Exercises, Philip simply seemed to follow the promptings of the Holy Spirit, who blows where she will. He had what today we may call a more internal, intuitive, feminine sensibility. Human nature is universal, but no two souls are the same, and Philip emphasized that.

I read somewhere that the word “silly” comes from a root meaning “happy” or “blessed.” Another word for blessed is saintly, and I wonder if, through cynicism and disillusionment, and maybe because of some really bad spiritual formation, being “saintly” came to seem plain “silly.” But kooky as Philip may have been in some ways, he had a prophetic, counter-cultural savvy that made him a presence to be reckoned with, not a simpleton to be pitied or patronized.

In an age when the Catholic Church was steeped in imperialism and imposed external structures on all facets of the faith, Philip worked from another, more intimate and mystical vantage. With a zany twist. While prelates fought heretics, threatened hell and struck fear into the hearts of lay people, Philip encouraged music and festivity. He gave bizarre penances.

One evening as his community gathered for supper in the community dining room, Philip had a penitent-friend make a grand entry with a monkey on his shoulder. The monkey wore a cardinal’s hat—the soccer ball biretta?—and carried a toy gun. Who knows what his sin was. This kind of theater was not a common practice. Philip sensed who could embrace and benefit from such a bizarre penance. He surely gained the penitent’s permission. He was careful and tender. He may have been a trickster, but never at a hurting person’s expense. His tricks sound like treats to me.