The support band that nearly made Bob Dylan quit music entirely: “It would be my last”

“I asked Bob Dylan why he does so many gigs,“ Pete Townshend once recalled. “He told me, ‘I’m a folk singer. A folk singer is only as good as his memory, and my memory is going.’ He’s doing it to keep his memory alive.” 

The so-called original vagabond is a wandering artist, born from the pages of On The Road and destined to keep his wayfaring story alive in the same way that it began. Like his hero, Woody Guthrie before him, songs are treasures you pop in a knapsack and march along the highways of this world, inspiring a sense of liberation with your wares. He knows no other way, and he wouldn’t have it any other way, either.

So, he has sauntered around the globe on his Never Ending Tour, establishing himself as the definitive modern folk singer. He doesn’t need to do it. He’d already go down as one of the greatest artists in human history without the expressionist shows he churns out, but he’s never done what he needs to do. He’s always done what he likes. But who said doing what you like all the time is easy?

Sometimes, there are potholes ahead, even on the roads you want to take, and Dylan has embraced a few on his memory lane.

Perhaps the sorest was when he hit the road with his younger pals. ”I’d been on an eighteen month tour with Tom Petty and The Heartbreakers. It would be my last,” he mournfully wrote in his 2004 memoir. ”I had no connection to any kind of inspiration. Whatever had been there to begin with had all vanished and shrunk. Tom was at the top of his game, and I was at the bottom of mine.”

BOB DYLAN , TOM PETTY, PERFORMING AT RICH STADIUM BUFFALO,
Credit: Alamy

Our hero was crushed. Young blood had swept him off of his tracks, and he was having to be bludgeoned by this reality night after night as The Heartbreakers seemingly soared to new heights with each passing show and Dylan sank ever lower. His albums weren’t doing much better in the charts, and it simply seemed like the world had moved on from the maestro.

The 1986 to 1987 True Confessions and Temples in Flames tour started Down Under in Wellington, New Zealand, and Dylan figured he never found his way back Up Top, so to speak. It was 90 shows of bloody hell.

Away from the stage, his latest studio album, Empire Burlesque, had been rightfully derided, even the gaudy cover showed a man out of step and out of sorts. As hard as it is to believe now, his reverence was waning. Touring with the most blossoming band of the moment turned out to be a bad move. ”I couldn’t overcome the odds,” he continues. ”Everything was smashed. My own songs had become strangers to me.” 

His fall from grace was hitting hard, and he was hating it. He might have been on friendly terms with Petty and his pals, but he felt, in no uncertain terms, that the tour was a disaster. ”It wasn’t my moment of history anymore,” he wrote. 

Adding, “There was a hollowing singing in my heart, and I couldn’t wait to retire and fold the tent. One more big payday with Petty and that would be it for me.” Given what he told Townshend, the gravitas of his heartbreak in this trying time really comes to the fore.

”I was what they called over the hill.… The mirror had swung around and I could see the future – an old actor fumbling in garbage cans outside the theatre of past triumphs,” he poetically concludes. This was as low as he had felt in his musical career. Petty might not have felt that his band were touring over him, but he noticed that his buddy was a little disheartened, telling Paul Zollo, ”It revealed he has insecurities like everyone else has.”

He continued, ”Because the thing is, when you’re that famous, people don’t often give you that benefit of the doubt, they kind of just assume that you understand how great you’re supposed to be. But the truth is, you’re only a human, and you’re still going to grow through everything that humans go through.”

Dylan was going through the wringer, and whether he knew it then or not, if you keep wandering long enough, you’ll find pleasant pastures once again – especially when you’re Bob Dylan, the most pivotal artist of the 20th century, and reinvention has always been your thing. Since this low ebb, Dylan has played thousands of shows, brandishing the depths of inspiration to present his wares in thrilling new ways each night. He’s a folk singer, after all.

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