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Stobgopper’s ‘I Made a Playlist:’ Late Career Dylan, Vol. 3

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Photo credit: David Gahr

What’s your feeling about Johnny Cash’s American Recordings sessions?

I know they’re universally lauded and gave Cash’s career a boost that had people returning to his earlier work…

…A good thing.

That said, I can’t get past the feeling that the later stuff simply took advantage of The Man in Black’s aged bark and worn visage and hitched it to unhappy or apocalyptic contemporary lyrics: Poof! Easy bake atmospherics.

I’m sure you have alternative takes.

My point being that Dylan could also have gone this route, and probably would have been successful.

I’m glad he didn’t, for the most part. He would take less successful tangents, but not in the Aughts.


Time Out of Mind,
1997

Dylan’s discography other than his official releases is a tangle of vines, underbrush, and old tree roots, otherwise known as, respectively, official bootlegs, live recordings, and greatest hits albums. 

Between 1993’s Good as I Been to You (previously and mistakenly attributed to 1992) and this one, we had an MTV Unplugged performance and a couple of Best Ofs. No bootlegs, even if he’s up to 18 of those as of now, one of which contains outtakes of TOOM. I invite you to listen to them all; I’m going out to shovel out the stables.

Time Out of Mind is regarded by many as the high point of Dylan’s post-peak career.

His take on aging in ‘Not Dark Yet’ resounds with both regret and a determination to keep dotage at bay; ‘Make You Feel My Love,’ while perhaps not one to add to your late-nite seduction playlist, finds Bob in a courting mood, even if ‘make you’ has uncomfortable connotations and ‘feel my love’ a distinctive ick factor.

Then there’s ‘Highlands.’ A return to the expansive scope of ‘Sad Eyed Lady of Lowlands’ and ‘Brownsville Girl,’ it’s another meandering journey that touches on Scotland, ordering breakfast in Boston, and avoiding feral dogs. He not only gets away with this kind of thing; it’s one of his touchstones, an aspect that makes Dylan ‘Dylan.’ We should treasure the man’s willingness and nerve to go full widescreen VistaVision on occasion.

*Note: five points deducted from Gryffindor’s total for not covering Steely Dan’s ‘Time Out of Mind.’ It was right there!

Gon’ walk down that dirt road
’Til my eyes start to bleed
Til there’s nothin’ left to see
’Til the chains have been shattered
And I been freed


Love and Theft
2001

Zimmerman in the 21st century.

Who among the avatars of ‘60s were still making vital music in the age of Staind and Nelly? Not the Lovin’ Spoonful, Donovan, or, unfortunately, the Four Tops. And yet, here we are, a soundtrack of the artist at 60, and it’s good, verging on great. It was also released on September 11, 2001, which was less good.

Dylan manages to shunt a lot of dichotomy into 12 tunes.

‘Tweedle Dee & Tweedle Dum’ is an energetic, quick-stepping shuffle. It’s also a screed aimed at a couple of ne’er-do-wells whose actions might be minor sins or ghastly crimes. It’s hard to tell which, and maybe Dylan doesn’t care: his view might be that all malfeasance is tragedy, no matter the scope or intent.

‘Summer Days’ sounds like a perfect beachy stomper, all upbeat rockabilly, but the last line of most verses undo the positivity of the first while the good times are bid adieu in the midst of enjoying said times.

Notably, the cover of Love and Theft introduces the world to Dylan’s pencil-thin mustache, one he’d sport for some time onward.

Combined with his hawk-like visage and a pile of hair that just stepped inside from a howling scirocco a few feet before the rest of him, he looks properly dissolute, a veteran survivor of the rock and roll wars.

Thing is, he also looks like he’s ready to get out there and do it again.

Samantha Brown
Lived in my house
For ‘bout four or five months

Don’t know how it looked
To other people
I never slept with her even once


Modern Times
2006

Ten tracks coming in at a not-so-tidy 63+ minutes.

So, yeah, a lot of ground to cover, a lot of rough-hewn vocals to let burr your eardrums, much content, many styles. The album’s single, ‘Someday Baby,’ is the shortest of the collection at 296 seconds or so, enough for Dylan to tell his recently departed lover how he’s going to get over her by verbally strafing her from various angles over the course of nine verses. That familiar vituperativeness is alive and well. As are his verbosity and high-toned doggerel tendencies. 

‘Spirit on the Water’ presages an upcoming left turn (into a ditch, from this perspective) from our Minnesota boy. It’s a minor key twinkler (is it in a minor key? IDK…), a love song whose architecture is borrowed from any number of Tin Pan Alley stalwarts, although neither ‘Honeysuckle Rose’ nor ‘Peg o’ My Heart’ contain lyrics like ‘I can’t go to paradise no more / I killed a man back there.’ 

As for the other masks Dylan tries on, he could do worse than the one he dons for ‘When the Deal Goes Down,’ a wordier George Jones weeper but just as effective.

‘Nettie Moore’ marches to a funereal beat as he explains to his titular woman how much trouble he’s gone through to keep her in his heart in a broken world, playing the love-worn traveling jongleur playing to a hushed crowd. And you can almost dance to ‘Thunder on the Mountain.’

He continues to flex his creative muscles while still recognizably the artist from his salad days. In others words, still interesting.

Well, I picked up a rose
And it poked through my clothes
I followed the winding stream
I heard the deafening noise
I felt transient joys
I know they’re not what they seem


Together Through Life
2009

Honeyed by David Hidalgo’s swinging accordion, his regular ‘Never-Ending Tour’ band bolstered by the Heartbreaker’s Mike Campbell, Dylan extends his critically-acclaimed geezer heater with this release.

It’s no Beggars/Bleed/Fingers/Exile run:

(What is?)

But at roughly the same age (mid- to late-60s and beyond), Keith and Mick were deep into their 18-year original content hiatus between A Bigger Bang and Hackney Diamonds. You can grade the Stones on a curve if you wish due to the disorganization and idiosyncrasies of group dynamics as well as founding members shedding their chains of mortality, but this is still a clear A-/B+ compared to a C situation.

Bobby kicks things off with ‘Beyond Here Lies Nothin’,’ which sounds bleaker than bleak but actually celebrates a love so transcendent, anything after it pales to the point of oblivion. You know he’s got it bad when he calls her ‘pretty baby.’

‘It’s All Good’ mines the fruitful seam of revealing the chasm between what is and what ‘they’ say, with the singer gleefully pointing out all the holes in ‘their’ false logic. ‘Jolene’ (not that ‘Jolene’) is a start-and-stop rocker about another woman our protagonist pines for.

All in all, TTL finishes up the last ‘era’ (baronial? noble?) of one of our most consequential artists, and does so uncompromisingly.

In the parlance of Townsend, it turns out that Dylan didn’t want to die before he got old, but to remain a consistent artistic force when he got old. This is where he gets off that particular trolley, though. I for one enjoyed the ride.

Well, there’s reasons for that
And reasons for this
I can’t think of any now
But I know they exist


I’m sittin’ in the sun
Til my skin turns brown
I just want to say
That hell’s my wife’s home town


The Playlist, part. 3

Time Out Of Mind

  • Dirt Road Blues
  • Highlands
  • Cold Irons Bound

Love and Theft

  • Tweedle Dee & Tweedle Dum
  • Honest With Me

Modern Times

  • Thunder on the Mountain

Together Through Life

  • If You Ever Go to Houston
  • It’s All Good

Up next: Final successes, but not before missteps.


Logo of TNOCS with the tagline "Looking Back. Living Forward." featuring a sun illustration.

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Virgindog
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Virgindog
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December 18, 2025 8:23 am

I’m not a consistent Dylan listener but I remember liking Modern Times. I’ll have to revisit it. Thanks, stob!

mt58
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mt58
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December 18, 2025 10:10 am

Nice new chapter in your Dylan playlist series, Stob.

Other than McCartney, I’m trying to think of an artist who would come under the category of “prolific artist who was an A+ lister, but soldiered on, albeit with diminished chart success,” as much as Dylan.

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