In retrospect, Bob Dylan’s career was in a fascinating position during the 1980s. Unlike any other time in his career, Dylan’s confidence was in crisis and his image began to slip. Amid a flurry of stadium-sized tours for his contemporaries, it was clear that he needed to revitalise his live act, and who better to assist him than Tom Petty.
It was 1986, and Tom Petty & The Heartbreakers were one of the world’s premier live acts, but when Dylan came calling, they dropped everything to join him on the road. Dylan was considering retirement and felt like his career was aimlessly meandering. He’d fallen out of favour with the industry, performing and was no longer in it for the right reasons.
In his memoirs, Dylan admitted he viewed the tour as “one more big payday with Petty, and that would be it for me. I was what they called over the hill.” However, the singer-songwriter enjoyed the run so much that he never wanted it to end.
Petty later revealed that the tour came about after Dylan was unhappy with his acoustic performance at Live Aid and asked them to back him at Farm Aid. Initially, it was meant to be a one-off performance, but after the show, Dylan asked if they’d like to join him on his True Confessions tour, which was duly accepted.
“We’d all been huge Dylan fans, and we were very intrigued by the idea of playing with Bob,” Petty once recalled. “So off we went. And that went on for two years. We’d do part of it and then more would get added on, and then more would get added on. We really did the world with Bob Dylan.”
Together, they were a perfect match, and seemingly, there was no reason the partnership would end. However, tragedy brought them to a premature divorce after Petty’s house was burned down in an arson attack, and suddenly, his professional life seemed insignificant in comparison.
“The fire happened in the middle of the Bob Dylan tour,” Petty once recalled. “I remember telling Bob, when we were in England at the end of the tour, that we were going to have to stop, as far as backing him up. I had to go back and sort out my life and my family, and find a home, and we needed to get back to just being The Heartbreakers. And we had really enjoyed it, and now he needed to get his own band, because we needed to get back to our own thing.
“Bob said, ‘No, we don’t want to break this up, it’s too good. And I said, ‘It is really good, but we kind of had our own agenda before we got into this.’ And he thought we could do both.”
If it wasn’t for the tragedy, perhaps, Petty would have carried on performing with Dylan. However, he was utterly exhausted, which is no surprise considering, on top of touring with Dylan, the Heartbreakers also recorded an album in 1987 and a headline tour. It was too much to balance, and while it was fun, the schedule was simply unsustainable for Petty.