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When Bob Dylan almost walked out on the Grateful Dead

Sat 25 March 2023 23:00, UK

It was one of the most legendary convergences in rock history: Bob Dylan would be touring with the Grateful Dead in 1987. Dylan had gotten in the habit of hiring famous bands to be his backing group, with Tom Petty & the Heartbreakers serving as Dylan’s band in 1986. The Heartbreakers were streamlined and powerful, but the Dead were something completely different – loose, jammy, and wanting to work with a much bigger setlist of songs than Petty.

“I needed to go rehearse with the band for these shows, so I went to San Rafael to meet with The Dead,” Dylan wrote in his book Chronicles. “I thought it would be as easy as jumping rope. After an hour or so, it became clear to me that the band wanted to rehearse more and different songs than I had been used to doing with [Tom] Petty. They wanted to run over all the songs, the ones they liked, the seldom-seen ones. I found myself in a peculiar position, and I could hear the brakes screeching. If I had known this to begin with, I might not have taken the dates.”

“I had no feelings for any of those songs and didn’t know how I could sing them with any intent,” Dylan admits. “A lot of them might have been only sung once anyway, the time that they’d been recorded. There were so many that I couldn’t tell which was which — I might even get the words to some mixed up with others. I needed sets of lyrics to understand what they were talking about, and when I saw the lyrics, especially to the older, more obscure songs, I couldn’t see how I could get this stuff off emotionally.”

“I felt like a goon and didn’t want to stick around. The whole thing might have been a mistake,” Dylan added. “I’d have to go someplace for the mentally ill and think about it. After saying that I’d left something at the hotel, I stepped back outside onto Front Street and started walking, put my head down against the drizzling rain. I wasn’t planning on going back. If you have to lie, you should do it quickly and as well as you can.”

Dylan was set to abandon the tour when he heard some inspiration. “I started up the street — maybe four or five or six blocks went by, and then I heard the sounds of a jazz combo playing up ahead. Walking past the door of a tiny bar, I looked in and saw that the musicians were playing at the opposite end of the room. It was raining, and there were few people inside. One of them was laughing at something. It looked like the last stop on the train to nowhere, and the air was filled with cigarette smoke. Something was calling to me to come in, and I entered, walked along the long, narrow bar to where the jazz cats were playing in the back on a raised platform in front of a brick wall.”

“I got within four feet of the stage and just stood there against the bar, ordered a gin and tonic and faced the singer. An older man, he wore a mohair suit, flat cap with a little brim and shiny necktie. The drummer had a rancher’s Stetson on, and the bassist and pianist were neatly dressed,” Dylan observed. “They played jazz ballads, stuff like ‘Time on My Hands’ and ‘Gloomy Sunday.’ The singer reminded me of Billy Eckstine. He wasn’t very forceful, but he didn’t have to be; he was relaxed but sang with natural power. Suddenly and without warning, it was like the guy had an open window to my soul. It was like he was saying, ‘You should do it this way.'”

“All of a sudden, I understood something faster than I ever did before. I could feel how he worked at getting his power, what he was doing to get at it. I knew where the power was coming from, and it wasn’t his voice, though the voice brought me sharply back to myself. ‘I used to do this thing,’ I’m thinking. It was a long time ago, and it had been automatic. No one had ever taught me. This technique was so elemental, so simple, and I’d forgotten it,” Dylan remembered. “It was like I’d forgotten how to button my own pants. I wondered if I could still do it. I wanted at least a chance to try. If I could in any way get close to handling this technique, I could get off this marathon stunt ride.”

Rejuvenated, Dylan began walking back to Front Street. “Returning to The Dead’s rehearsal hall as if nothing had happened, I picked it up where we had left off, couldn’t wait to get started — taking one of the songs that they wanted to do, seeing if I could sing it using the same method that the old singer used. I had a premonition something would happen. At first, it was hard going, like drilling through a brick wall. All I did was taste the dust. But then miraculously something internal came unhinged.”

“In the beginning, all I could get out was a blood-choked coughing grunt, and it blasted up from the bottom of my lower self, but it bypassed my brain. That had never happened before,” Dylan claimed. “It burned, but I was awake. The scheme wasn’t sewed up too tight, would need a lot of stitches, but I grasped the idea. I had to concentrate like mad because I was having to manoeuvre more than one stratagem at the same time, but now I knew I could perform any of these songs without them having to be restricted to the world of words. This was revelatory.”

From that point on, Dylan was game for any and all songs that the Dead were going to throw at him. “I played these shows with The Dead and never had to think twice about it. Maybe they just dropped something in my drink, I can’t say, but anything they wanted to do was fine with me,” Dylan concluded. “I had that old jazz singer to thank.”

Check out Dylan playing with the Dead in 1987 down below.