It was the bizarre photo that somehow managed to cut through all the dissection and celebration surrounding the Blue-nami Democratic wave wins in the midterm elections on Wednesday (Nov. 4). Bob Dylan, dressed in his by-now-familiar dark hoodie, hood up, meeting with the first American-born pontiff, Pope Leo XIV, at the Vatican.
Minnesota native Dylan — who performed for and met Pope John Paul II in 1997 — had a private audience with Chicago-bred Pope Leo during which he wore his hoodie, along with a black jacket, black zip-up, loosely tied polka dot black tie and black pants. According to the Vatican, the pope gave the Nobel Prize-winning folk icon a rosary and Dylan in turn gave the leader of the Catholic Church a copy of his Chronicles: Volume One memoir.
Though the sight of the two men launched hundreds of memes and quips about their big mismatched crime-solving duo energy, it was not the first time the American Pope has met with a popular musician or hosted them at the Vatican for a special event. In fact, the 71-year-old religious leader whose papacy began on May 8, 2025 has met with a number and hosted special events with a number of rock, pop, opera and Latin artists since ascending to the papacy last year.
From meeting with punk legend Patti Smith, Bad Bunny and Italian singer Laura Pausini, to attending concerts by crooner Michael Bublé and Italian conductor Riccardo Muti, Pope Leo has enjoyed audiences with a number of bold-faced names, in addition to overseeing (but not attending) last September’s Grace for the World show in St. Peter’s Square that featured Bocelli, Karol G, Pharrell Williams, John Legend and Jennifer Hudson.
Check out a list of six of Pope Leo’s top musical encounter moments below.
