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In Search of the Best Bob Dylan

America's musical alchemist has been a fixture since the '60s. Yet his greatest work might surprise you.
Bob Dylan

One of the most cherished pastimes of diehard Bob Dylan fans is arguing over your “favorite Dylan.” The top contenders are obvious: the mid-Sixties Dylan, gaunt with eyes hidden behind the ever-present black shades, antagonizing audiences with ear-splitting renditions of “Ballad of a Thin Man” and “Like a Rolling Stone” while dragging America into the decade kicking and screaming. Then there was the mid-Seventies Dylan of “Tangled Up in Blue” and “One More Cup of Coffee,” the Dylan who during the long process of separation and divorce from his wife Sara seemed more grounded and more vulnerable than he’d ever been. And of course, there’s the early Sixties folk singer, the court jester of Greenwich Village, appearing nearly fully formed out of the city steam like an heir of Woody Guthrie, writing songs like “Blowin’ in the Wind” on napkins in all-night coffee shops.

The problem with picking a favorite Dylan is that there are so many strong contenders. You could even make a case for the New Morning Dylan of the late ’60s or the born-again Christian Dylan, a totally underrated phase of his career. Obviously, no answer is final and the game itself is kind of a moronic trap. But this is what fans do. We love coming up with hypotheticals and arbitrary rankings, anything that lets the analytical parts of our minds engage with the art that throws its colors on our soul. And so, in the spirit of playful analysis, I’d like to make a controversial claim: the best Dylan was the Dylan of 1997 to 2001.

I know. Pause. Breathe. Take it in. And let me explain myself.

Ever since Dylan’s long and by all accounts gut-wrenching divorce, he’d been meandering artistically. You might name the beginning of his long nadir as the disappointing “Night of the Hurricane II” fundraiser for the eponymous Rubin “Hurricane” Carter of Dylan’s hit song off of Desire. As Daniel Mark Epstein writes in The Ballad of Bob Dylan, the concert to raise legal funds for the boxer who was in all actuality probably guilty of murder “was not successful by any standard – financial, artistic, or moral.” Even with a lineup of stars like Stevie Wonder and Stephen Stills, the show failed to fill much more than half of the Houston Astrodome. Egos clashed, solos lasted too long, and a kind of sad moral dissipation, perhaps a reflection of the era itself, filled the air. It would be the last time Dylan performed the achingly beautiful tribute to his estranged wife “Sara” live.

After the final “Rolling Thunder” tour, a depressing and meandering affair in which shows frequently had to be cancelled due to poor ticket sales, Dylan entered his own long dark night of the soul. It would last for about a decade. During that time he struggled, searched, and drank. All through the late Seventies and most of the Eighties, he seemed lost. Which isn’t to say that he didn’t write some good songs. “Ring Them Bells,” “Changing of the Guard,” “Jokerman,” etc. But the magic seemed gone. And what’s worse, it seemed like he no longer enjoyed performing. He was a beaten down man whose performances felt perfunctory at best. In his memoir Chronicles, he talks about feeling like a “done for, an empty burned out wreck” during his dark decade. And his music certainly reflected that. Dylan, the amorphous mercurial alchemist who once had access to so many different selves, felt like he had a “missing person” inside of himself.

Finding that lost person didn’t come all at once but over a sort of series of watershed experiences in the late Eighties. Each centered on reconnecting with live performance, the most significant of which was his tour with the Grateful Dead. This shouldn’t be surprising. The Dead are the preeminent live rock band, in the Guinness Book of Records for most live performances, and in their shows channel a vast current of music that stretches from Tchaikovksy to Chuck Berry, from Johnny Cash to Miles Davis. Listening to a Dead show is like flipping through stations on some mid-century Art Deco Zenith shortwave radio, the warm glow of life coming out of the tubes while waves arc down from the atmosphere. It might have reminded Dylan of his own childhood in Hibbing, Minnesota, hugging the radio at night with far-off bluegrass and gospel stations whispering through the falling snow.

Regardless of how the shows actually sounded (the consensus is usually “not great”), the experience wakened something in Dylan. He hadn’t quite rediscovered his muse, but he was on the path again. And most importantly, he was comfortable playing live again. More than comfortable even, he craved it. In the summer of 1988, Dylan began his Never Ending Tour, in which he was (until COVID) constantly touring, playing upwards of 100 shows a year. Dylan himself has been dismissive of the categorization, saying in a 2009 Rolling Stone interview:

Critics should know there is no such thing as forever. Does anybody call Henry Ford a Never Ending Car Builder? Anybody ever say that Duke Ellington was on a Never Ending Bandstand Tour? These days, people are lucky to have a job. Any job. So critics might be uncomfortable with my working so much. Anybody with a trade can work as long as they want. A carpenter, an electrician. They don’t necessarily need to retire.

Regardless, he’s played over 3,000 shows since 1988 alongside a backing band that has changed a bit here and there but has remained masterful through each of its subtle incarnations.

So Dylan was reborn through the Dead. Then he sort of created a Dylan-esque version of their constant touring. In the studio, besides a middling Oh, Mercy and some interesting but not necessarily inspired albums of acoustic folk covers, Dylan’s rediscovered self hadn’t made an appearance in the studio. The first real indication that Dylan had returned to form was 1997’s Time Out Of Mind. Recorded in what was by most accounts an emotionally tense atmosphere (he and producer Daniel Lanois didn’t speak to each other directly throughout much of the recording process), the album is a deep dive into the brokenness of human connection. It’s raw, with a pained energy that courses through each track like a third rail.

The mood of the songs is smoky and distant, even if the lyrics are direct. We feel like we’re sitting at a bar with someone who has seen it all and lived to tell the tale. And in a way, that’s exactly what it is. It’s Dylan taking account of everything in his life up to that moment. The language, a mishmash of high poetry, slang, cliché, and bawdy humor, holds sadness and gratitude together in a shared syntax. In other words, it’s pure wisdom. A personal favorite of mine is the song “Not Dark Yet,” a slow, sad lament about the mystery of change and death. The following is from the final verse:

I was born here, and I’ll die here
Against my will
I know it looks like I’m moving
But I’m standing still
Every nerve in my body
Is so vacant and numb
I can’t even remember what it was
I came here to get away from
Don’t even hear a murmur of a prayer

It’s not dark yet

But it’s getting there.

This isn’t the idealist folk Dylan. It’s not the surreal poet pumped up on speed. It’s not even the sad divorce Dylan of the Seventies. It’s a Dylan who had experienced what Simone Weil calls “affliction”. He was a man who, having lost so much, had learned to be grateful through the tears. What do we call this Dylan? Let’s call him the Ghost Dylan. Able to in turns inhabit each incarnation of himself, shifting from phrase to phrase, Ghost Dylan has in a sense died to his own ego in order to become the superior craftsman.

Time Out Of Mind won a Grammy for best album, but his next album, 2001’s Love and Theft, is arguably even better. If his 1997 album was intense, raw, and almost emotionally claustrophobic, Love and Theft was broad, expansive, and outward facing. As Epstein again writes, “The character Dylan brought to the Love and Theft sessions is a magpie collector of old songs, jokes, and stories, a minstrel show interlocutor, the sort of gaffer Yeats says may come ‘proud, open-eyed and laughing to the tomb’.” There’s a real Basement Tapes feel to Love and Theft, with a broad musical palette that includes Delta Blues, swing, rockabilly, and even show tunes. This album belongs in any discussion of Dylan’s best, simply by virtue of its skillfully holding such a wide swath of humanity in its words and sound. The standout track must be “Mississippi,” a song written years prior that never really found a proper home until the Love and Theft sessions. From the final verses:

My clothes are wet, tight on my skin
Not as tight as the corner that I painted myself in
I know that fortune is waiting’ to be kind
So give me your hand and say you’ll be mine

Well, the emptiness is endless, cold as the clay
You can always come back, but you can’t come back all the way
Only one thing I did wrong
Stayed in Mississippi a day too long

These albums don’t feel like the work of a man long in decline, who peaked decades prior. They feel like the culmination not just of a career, but of a fascinating life full of pain and pleasure, twists and turns. Incorporating scraps of myth and folk legend, mixing it with original observations and a wry sense of humor, this a Dylan as deeply engaged with the mytho-poetic tradition as ever. As Eliot said of tradition, “you must obtain it with great labor.” The ’97-’01 Dylan had experienced that struggle, had labored hard to put himself back in touch with the tradition of the troubadour and poet after the connection had been all but severed. In Time Out of Mind you feel the pain of that severance. In Love and Theft you feel the joy of return.

I know not many will be convinced to rank my Dylan above theirs. Maybe that’s how it should be. Timing is everything in art. It has to hit us at the right moment. Most people heap praise on the Dylan they first fell in love with, and I was a senior in high school when Love and Theft was released. But anyone with even a passing interest in Dylan as an artist should take a second look at this phase of his career. A young talent like Dylan was rare, but to maintain it, lose it, and then rediscover it through agonizing labor and thousands of live shows is even rarer still. It seems appropriate to give the last words to Dylan himself, from the ending to his 16-minute epic “Highlands” off of Time Out Of Mind:

The sun is beginning to shine on me
But it’s not like the sun that used to be
The party’s over and there’s less and less to say
I got new eyes
Everything looks far away

Well, my heart’s in the Highlands at the break of day
Over the hills and far away
There’s a way to get there and I’ll figure it out somehow
But I’m already there in my mind
And that’s good enough for now