Bob Dylan made a career out of disappointing his fans by doing whatever he wanted. In 1997 he got the opportunity to disappoint the pope.

On September 27, 1997, three days before the release of Time Out of Mind, Dylan and his band performed three songs at the 23rd World Eucharistic Congress in Bologna, Italy in the presence of Pope John Paul II, who sat on a dais off to the side of the stage. It was a strange scene, with the pope and his entourage watching Dylan in his cowboy hat and western wear, and his touring band on stage (Bucky Baxter, still rocking that slide guitar!). This wasn’t part of a major Dylan tour – he had played the US that summer – rather it was a papal invitation. Dylan, being Dylan, tacked on a few shows in the UK on the way home.

The scene was more than a little bizarre. 300,000 young Catholics gathered to listen to the pope, who based at least part of his sermon on Dylan’s lyrics. Dylan performed two songs – “Knockin’ on Heaven’s Door” (the title is apt, though probably not the lyrics generally) and “A Hard Rain’s a-Gonna Fall” before the pope spoke. You can see both of those songs here (the whole event aired on RAI UNO in Italy):

After Dylan met him, John Paul spoke to the crowd, basing at least  part of his sermon on Dylan’s lyrics:

A representative of yours has just said on your behalf that the answer to the questions of your life “is blowing in the wind”. It is true! But not in the wind which blows everything away in empty whirls, but the wind which is the breath and voice of the Spirit, a voice that calls and says: “come!” (cf. Jn 3:8; Rv 22:17).

You asked me: How many roads must a man walk down before you call him a man? I answer you: one! There is only one road for man and it is Christ, who said: “I am the way” (Jn 14:6). He is the road of truth, the way of life.
And, of course, speaking after the pope himself (tough act to follow), Dylan didn’t actually sing the requested and referenced song, instead closing the whole event with “Forever Young”. Sure, it’s got “May God bless and keep you always…” but Dylan certainly has written a lot of songs that would have been more appropriate. If you’re going to turn the request of the pope at a command performance, I mean that’s marching to your own drummer!

(According to Bjorner’s site, he didn’t even rehearse “Blowin’” at the soundcheck – though he did do “Maggie’s Farm” and “With God On Our Side”. What I wouldn’t give for a video of Bob Dylan singing “With God On Our Side” while the pope watched!)

Pope Benedict, then Cardinal Ratzinger, must have been at the sound check, because in his memoir of his predecessor he wrote that he didn’t want Dylan there. About the event:

The pope appeared tired, exhausted. At that very moment the stars arrived, Bob Dylan and others whose names I do not remember. They had a completely different message from the one which the pope had. There was reason to be skeptical I was, and in some ways I still am over whether it was really right to allow this type of ‘prophet’ to appear.

Wow. You probably have to live a pretty special life to play for one pope while another calls you a “prophet” with full-on scare quotes.

Here’s the video of Dylan actually meeting John Paul II (it isn’t included in the video up top). I wonder who was more impressed with the other? Actually, if you check at 5:34 of the video up top, you can tell that John Paul lacked enthusiasm for the whole thing.