Most critics tend to use the word “abysmal” when writing about Bob Dylan's 1987 tour with the Grateful Dead. But despite the lackluster performances on the Dylan & the Dead live album released two years later, touring with the Dead provided Dylan with a sorely needed avenue of rediscovery. In fact, were it not for this pairing of major talent, Dylan might not even be touring today. Or so he says.
On tour with Tom Petty and the Heartbreakers in 1986-87, Dylan had reached the nadir of his worst artistic slump, and was even considering hanging up his harp rack. Every time he took the stage, Bob was reminded that the majority of fans came to see, not him, but Petty. As Dylan wrote in his 2004 autobiography, Chronicles, “I had no connection to any kind of inspiration.... Tom was at the top of his game and I was at the bottom of mine... My own songs had become strangers to me... It wasn't my moment of history anymore... Try as I might, the engines wouldn't start.”
To fill in a tour gap, Dylan signed on for a string of stadium shows with the Grateful Dead. But when he went to Marin County to rehearse, Dead front man Jerry Garcia insisted on running through obscure songs like “John Brown” and “The Wicked Messenger,” stuff Dylan had no interest in playing. “I found myself in a peculiar position and I could hear the brakes screech,” wrote Dylan. “I had no feelings for any of those songs.”
Dylan snuck out of the rehearsals with no intention of returning. Stopping at a nearby club and listening to an old jazz singer, Dylan had an epiphany, recalling a technique he once employed that gave his songs new meaning and range. “It was like the guy had an open window to my soul,” Dylan wrote. “I could feel how he worked at getting his power... This technique was so elemental, so simple and I'd forgotten.”
Dylan returned to the rehearsals, gave it a whirl, and voila! It worked. “I played those 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. I had that old jazz singer to thank.” This new ability to reconnect with and recast his old material was a pivotal breakthrough.
Dylan's Miracle Ticket
By the time Dylan embarked on tour with the Dead in 1987, he'd already lost a major chunk of his '60s and '70s fan base. Shortly after the release of Desire in 1976, Dylan converted to Christianity, cutting his gospel album trilogy, Slow Train Coming, Saved, and Shot of Love between 1978-81. Predictably, many longtime fans felt alienated by Dylan's new non-secular repertoire with its apocalyptic messages as Dylan, playing none of his older songs, used the stage as a stump to spread God's word. Even his 1983 release of Infidels (the album title indicating a return to the profane) couldn't win back Dylan's bedrock audience.
By 1987, the Grateful Dead, notorious for covering Dylan's songs in concert, was reaping the wind with their wildly popular “Touch of Grey” video. Seemingly overnight, the Bay Area vets went from playing half-empty arenas to filling entire football stadiums as the MTV generation bought the ticket and took the ride. For Dylan, a tour with the Dead would have obvious benefits, introducing a new bumper crop of budding cafe liberals and post-pubescent Reagan babies to the premier '60s musical icon. The harvest would be immense.
Another thing Dylan picked up from the Dead was the nonstop tour. Seasoned road warriors, after the 1960s the Dead simply never quit touring. And wisely so; throwing together a tour every couple of years in support of a new album requires amassing equipment rentals, arranging transportation, putting together a crew, rehearsals—an organizational nightmare. The logic is simple: once you have the wheels in motion, why shut the machine down? In February 1988, shortly after his stint with the Dead, Dylan's “Never Ending Tour” began and continues today.
Robert Hunter Collaborations
On almost parallel early '60s career paths, while Dylan was making inroads into the folk scene of Greenwich Village, Grateful Dead lyricist Robert Hunter was doing the same thing in the cafes of San Francisco. It was inevitable those paths would eventually collide. The two prolific craftsmen first conspired on Dylan's 1988 album Down in the Groove, penning “The Ugliest Girl in the World” and “Silvio." But it would be another three decades before the two would team up again, this time for Dylan's 2009 album Together Through Life.
Nothing piques Dylan's muse like a homework assignment, especially the movie soundtrack kind. Asked by French director Olivier Dahan to contribute a tune for his film My Own Love Song, Dylan whipped up “Life Is Hard.” Duly inspired, this one-song challenge morphed into an entire album project, with Hunter's signature on nine of the 10 tracks. As Dylan told Rolling Stone: “Hunter is an old buddy... He’s got a way with words and I do too. We both write a different type of song than what passes today for songwriting.”
In 1989, Dylan proposed joining the Grateful Dead, and the Dead politely declined. But regardless, Dylan toured with them one more time, as their opening act in 1995. Between June 15-25, Dylan did five shows, beginning in Highgate, Vermont and ending at RFK stadium, when Jerry Garcia joined Dylan on stage for rare duets of “It Takes a Lot to Laugh, It Takes a Train to Cry” and “Rainy Day Women #12 & 35” (it was the eighth to last show Garcia would ever perform). Playing mostly electric guitar, here's Dylan's set list for the Highgate show, where 30,000 ticketless fans showed up and infamously crashed the gate:
Crash On The Levee (Down In The Flood)
It Takes A Lot To Laugh, It Takes A Train To Cry
All Along The Watchtower
Tears Of Rage
Mr. Tambourine Man (acoustic)
Masters Of War (acoustic)
It's All Over Now, Baby Blue (acoustic)
Stuck Inside Of Mobile With The Memphis Blues Again
She Belongs To Me
Highway 61 Revisited
Encore: Like A Rolling Stone
After Garcia's death, Dylan would again tour with the newly incarnated band, The Dead (sans Jerry), and also with bass player Phil Lesh's Dead spinoff band, Phil Lesh and Friends.