Bob Dylan turns 85 this spring, just before Memorial Day. I went to see him Monday night in Waukegan, at the Genesee Theatre, itself approaching 100 years next winter. Nobody’s getting younger. Everyone’s retracing their steps. Dylan, being Dylan, is just doing it in a Dylan-y fashion. He’s playing a few large cities but mainly sticking to small towns, out-of-the-way haunts. Of course, he’s done this for years, on and off: His so-called Never-Ending Tour — a name coined by fans that he himself doesn’t use — started in 1988 in a 12,000-seat pavilion near San Francisco, and after 38 years, it’d be hard not to retrace.
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But the man is trying.
Muncie, Rockford, La Crosse, Dothan, Tyler, Iowa City, Troutdale, Woodinville. That’s where he’s playing this spring. Doesn’t matter the states. You know the places even if you’ve never visited. Old movie houses and such, a couple of thousand seats, surrounded by town squares and empty storefronts, the kind that thrived before Dylan was Dylan, when his only stages in Illinois were brief appearances, at the Bear Folk Club off Michigan Avenue and Studs Terkel’s radio show in 1963.
A year later, he played his first full show here, at Ravinia Festival in Highland Park. The four-page program for the night begins: “There are few healthier signs of our times than that many of our young people heed and respect the grim pessimism of Bob Dylan.”
Could you imagine that in 2026?
A respectable Midwest institution applauding gloom?
Things have changed. The man himself now looks of a piece with small-town America, weathered, standing. He walked out Monday night wearing a white windbreaker with the hood pulled upward over his head, and remained that way all night, like Lawrence of Lands’ End. The closest the Genesee came to pessimism was a Dylan T-shirt or two in the lobby with a skeleton wearing a top hat. And yet, there is an undeniable winding down to Dylan’s performances these days, not genuine decline — he’s made some of his most interesting music in the past 30 years — but more like an ongoing reckoning with legacy and age. He sang in that famous defiant whine: “I’ll keep the path open / The path in my mind / I’ll see to it that there’s no love left behind.”
And this: “I ain’t no false prophet / I just know what I know.” As always, he doesn’t give you what you want, though by now I suspect his audience knows. He’s been right-sizing for decades, never parading hits or celebrating the anniversary of this or that, just turning his songs in his hands, rethinking.
Which means, there’s no reverence for classics. Nothing’s sacred. “When I Paint My Masterpiece” was remade as a mambo, “All Along the Watchtower” opened with a pulsing beat that seemed to draw on those intense opening chords from “Psycho Killer” by Talking Heads. Dylan’s become a Flying Wallenda, pulling arrangements out of shape, not looking down to see just how precarious all of this sounds, as his excellent four-piece band turns towards him, carefully watching his footing.
It’s also just a weirdly cozy image for a famously caustic legend.
Only a few stray bulbs lit the stage. Electric guitars were replaced with acoustics and the occasional upright bass. Tempos shuffled and strolled. Dylan sat behind a keyboard, a pair of microphones set too far from his face, so his voice broke in and out of focus. It was borderline maddening at first — then kind of worked. The effect grew dream-like, almost David Lynchian, like an AM radio playing faintly at two in the morning, tuning in nothing but forgotten early rock ‘n’ roll singles and rockabilly and a little country. A pair of late-‘50s-early-‘60s covers, Bo Diddley’s “I Can Tell,” and Eddie Cochran’s “Nervous Breakdown” (really a rewriting of “Summertime Blues”), completed the image.
The centerpiece of the show, though, as it has been on most of Dylan’s recent tours, was on his last 30 years, the shadow catalog he’s assembled to his ‘60s-‘70s classics; in particular, he leans into a late-career masterpiece, 2020’s “Rough and Rowdy Ways.” And those songs trudge, Tom Waits-like, only to unwind, long and dense, full of allusions to history and Greek myth and film noir and pop culture and mentors and friends, plus death and apocalypse. According to Robert Polito, author and former president of the Poetry Foundation, Dylan’s late-career songs are a “ghost language,” a collage of memories. His new book, “After the Flood: Inside Bob Dylan’s Memory Palace,” the best Dylan book in ages (and a must-read after any strange late-career Dylan show), makes a compelling case for why the last decades of Dylan’s works, however less known, are as meaningful as the early years that made him a superstar.
He imagines Dylan today reinvented as a sort of Simonides of Ceos, the Greek poet who escaped the collapse of a banquet hall, but was so observant and tuned in to his time and place he reconstructed the hall and identified the very spots where his dead friends were crushed, so that family and history would know where they fell. As a metaphor for Dylan, it’s spot on. The songs he played in Waukegan were heavy with reapers and wars and men in black coats, but what came across most was gratitude and borrowed time. He closed with his usual, “Every Grain of Sand,” but it’s a touching end, as vulnerable as Dylan’s ever allowed himself: “I hear the ancient footsteps like the motion of the sea / Sometimes I turn, there’s someone there, other times it’s only me.”
Presumably Bob Dylan will tour until he’s dead.
The day that happens, I hope I’m out of town. It’ll be worse than the outpouring of grief for Bowie, only uglier, because unlike Bowie, there’s little that is naturally likable about Dylan. He never played king of the goblins in a Jim Henson film. Just imagine all the hot takes and the half-felt appreciations, all those hosannas and the cliches about a guy who couldn’t stomach them, alongside the I-never-liked-him-anyway Facebook posts, the you-know-I-never-got-Dylan confessions, and the worst-concert-I-ever-saw op-eds. How could we remember a legend who never really stayed away for long, who kept making provocative work past the sell-by date, a mysterious figure forever out of reach?
I imagine he wouldn’t want the reverence, but wouldn’t mind it, either.
Here is, after all, a guy who put himself in the tradition of Homer in his Nobel Prize speech (which he didn’t deliver himself, because he didn’t attend). Except he did it with humor and casualness, as if to say we are all one road trip away from an Odyssey: “In a lot of ways, some of these same things have happened to you. You too have had drugs dropped into your wine. You too have shared a bed with the wrong woman. … You have angered people you should not have. And you have rambled this country all around. And you’ve felt that ill wind, the one that blows you no good, and that’s still not all of it.”
Next stop, Grand Rapids.