Bob meets Leo

Bob Dylan dropped in at the Vatican Nov. 4 for a private audience with Pope Leo XIV. According to the Vatican, the brief encounter featured "greetings and a few lighthearted exchanges."

The pope gave Dylan a rosary, and Dylan left Leo with a copy of his autobiographical book, Chronicles: Volume One. Dylan, 85, showed up for the meeting dressed in the black hoodie he's been wearing consistently on his 2026 tour dates (he's playing in Rome Nov. 5.)

It's not the first time Dylan has met a pope. The singer performed at a church-sponsored youth festival in Bologna, Italy, in 1997, with Pope John Paul II in attendance just off the main stage. Afterward, Dylan walked over and greeted the Polish pontiff.

It was an encounter that prompted some internal Vatican dissent, including from the man who would succeed JPII as pope, Cardinal Joseph Ratzinger.

I wrote about it in my book The Vatican Diaries, in a chapter profiling Pope Benedict XVI:

The first thing I noticed was the twitching leg. It was dark backstage, but I could make out the slight figure standing at the edge of the platform. He wore a black suit with a white stripe running down the side, and his right leg was jerking up and down involuntarily. It had to be Dylan. And he must be nervous, I thought. Singing for the pope was not an everyday thing.

A few moments later Bob Dylan and his band took the stage, and ripped into “Knockin’ on Heaven’s Door.” A roar went up from the vast fairgrounds in Bologna where more than 350,000 young people got to their feet. They had come not only to hear Dylan and the assorted rock bands that performed that evening but to witness an encounter of two cultural icons. Pope John Paul II sat in an alcove on the right of the stage, hand in chin, listening as Dylan segued into “A Hard Rain’s A-Gonna Fall” and closed with “Forever Young.”

Then Dylan walked over to the pope, beige cowboy hat in hand, and—after nearly tripping over a step—bowed and shook the Polish pontiff’s hand. The pope spoke into Dylan’s ear and smiled.

In the press perch, I sat next to Phil Pullella of Reuters and watched all this in a state of awe. It was 1997, and both John Paul and Dylan seemed genuinely moved. The entire event sounded like something a PR agent might dream up but would never come to pass: Dylan, the born-again minstrel who was just recovering from a near fatal illness, performing at a Eucharistic Congress where a giant cross dominated the stage; the pope then offering a verbal riff on “Blowin’ in the Wind,” using the lyrics to evoke the action of the Holy Spirit.

The concert, broadcast live by Italian state television, was hailed by just about everyone. Church organizers were ecstatic. It had pushed the limits of John Paul II’s interaction with popular culture, but in the end it worked. What better way to connect with young people today? There was one strongly dissenting voice at the Vatican, though. Cardinal Joseph Ratzinger, the Vatican’s doctrinal watchdog, let it be known that he thought letting an increasingly frail and ailing pope share the stage with a group of rock and pop stars was a bad idea. Ratzinger argued that Dylan and his musical confreres had a completely different message than the pope. They were “false prophets,” and showcasing them at a Eucharistic congress was the ultimate folly.

When Cardinal Ratzinger was elected to succeed John Paul eight years later, I remembered this episode—minor in itself, but a clue to reading the mind-set of the new pope. For years I had figured that Ratzinger, a piano-playing Mozart aficionado, simply didn’t like modern music. But as I watched Pope Benedict operate, I realized that his views were more complicated than that. To Benedict, Dylan was the quintessential symbol of the 1960s protest movement, with an antiauthoritarian bent that made him dangerous. He represented an open challenge to the old order of things. And while some of Dylan’s songs may have been inspired by Christianity and the Bible, this type of music lacked the gravitas of a requiem or even a decent liturgical hymn. It was artistic, but it didn’t harmonize with tradition. Ergo, it wasn’t to be trusted.

As became increasingly apparent after his election, this perspective on popular culture was typical of Pope Benedict. He felt safe only within a very circumscribed ecclesial environment, the sheltered realm of faith and church. Outside those borders, there were no real answers, and nothing really to be learned. To Benedict, the outside world was full of impurities and illusions that, unfortunately, had seeped into some sectors of the Catholic Church. And although he would never have said it aloud, part of the reason had been Pope John Paul’s penchant for reaching out and making connections with people who had little to do with the faith—journalists and sports heroes, aboriginal dancers and rock stars. It bought the church publicity, but at what price? With Benedict, the era of slumming with the stars would come to an end.

The Vatican’s annual Christmas concert was one of those crossover events that, in Pope Benedict’s view, had brought the church more harm than good. For thirteen years pop and rock stars had been coming to the Vatican to perform in a benefit and share the limelight with Pope John Paul; past luminaries had included Whitney Houston, Dionne Warwick, Gloria Gaynor, John Denver, Tom Jones and Lionel Richie. B.B. King had even given the Polish pope one of his electric guitars. It was primarily a feel-good event, though there had been occasional controversies. In 2003 the American singer Lauryn Hill had stunned the concert audience when she asked church leaders to “repent” for the abuse of children by priests. (The Vatican dismissed her impromptu outburst as a “sour note.”) In late 2005, as Pope Benedict prepared to host his first Christmas concert, organizers received word that Brazilian singer Daniela Mercury might use her Vatican slot to promote the use of condoms against AIDS. She was immediately dropped from the program. When Benedict learned of the controversy, he decided not to meet with any of the concert performers that year. It just wasn’t worth the trouble. The following year the concert was discontinued altogether. It was a small step in Benedict’s great program for the church, a program that might be summed up in a single word: decontamination.