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Stobgopper’s ‘I Made a Playlist:’Late Career Dylan, Vol. 2

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Which performers would I have loved to make a late career playlist for – but can’t?

The Police:

Unless you consider Sting’s solo career a viable path into irrelevancy. 

Dream of the Blue Turtles, anyone?

The Beatles and Led Zeppelin:

Giants whose existences as bands were prematurely cut off. Although, looking back:

They perfectly inhabited and encapsulated their respective decades before the end.

Dire Straits:

Had one ‘late career’ album, the less-than-well-regarded On Every Street 

(TBH, every DS record is considered at least an 8 out of 10 from this end. Fight me!).

I doubt you want to read my exegesis on ‘The Bug.’

Also: Marvin. Fine Young Cannibals. The Doors.

Velvet Revolver… 


Oh, Mercy
1989

I read Chronicles: Volume 1, published in 2004 and written by the great man hisself. The promised Volumes 2 and 3 remain in the gestatory stage, I guess, dwelling in the same accursed dimension as The Winds of Winter and the second part of Lewisohn’s All These Years.

It’s an evocative text made even more so if you read it in Dylan’s gravelly hoot. A large part of the book describes recording this album, hailed as his seventh or twelfth artistic rebirth and produced by noted Quebecois and U2 dial twiddler Daniel Lanois. ‘The Man in the Long Black Coat’ overflows with apocalyptic imagery so thick Dylan must have been reading The Stand while composing it.

Joan Osborne covered the song in ’95. Her clear, yearning vocal twists the narrative into a possible confessional: Is the ‘she’ who leaves with the titular character the singer herself? Dylan croaks the thing out in a martial beat, as if declaiming iambic pentameter from the roiling heavens, lightning bolt at the ready.

We live in a political world
Under the microscope
You can travel anywhere and hang yourself there
You always got more than enough rope


Under the Red Sky
1990

Here’s a unique take: this one’s critically controversial. No! Not a ‘90s Dylan album! Slash appears on one track; he didn’t enjoy the experience. So does George, mid-Wilburys, so he was most likely having a better time.

You can make a case reading the album’s track list it was actually the soundtrack to a proposed Fraggle Rock movie. Bob may have been writing all this for his four year-old daughter, which is fine, but why the desolate title and even more desolate album cover? It’s no Goodnight Moon. 

However:

That might be an answer. You got me. ‘God Knows,’ however, circles around its central conceit of knowing what God knows, even if God knows that you don’t really know, and what you don’t know is so vast, it doesn’t fit into a three-minute pop song, so we’re just gonna fade out here before you embarrass yourself further. And, God says, that’s all I’ve got to say to you.

Three by three, they danced on the sea
Four by four, they danced on the shore
Five by five, they tried to survive
Six by six, they were playing with tricks


Good as I Been to You
1992

A full-on acoustic folkie covers album, featuring everything from Stephen Foster to one of the most popular bops of the mid-16th century. There’s a feel of Dylan’s debut all over GAIBTY, even if after all these years he can’t conjure up the effortless cool and interpretive genius laid down in ’62, baby-faced and warbling through ‘You’re No Good.’

Instead and not surprisingly, it’s the wizened elder statesmen and his weary rasp teasing at the fabric of standards like ‘Blackjack Davey’ and ‘You’re Gonna Quit Me.’ This was far from a commercial vehicle at the time; if he’d waited 10 years and caught the O Brother Where Art Thou wave, it might have been bigger seller.

If that’s even what he was chasing at this point. Still, the album’s well thought of, both contemporarily and currently.


World Gone Wrong
1993

Good as I Been to You’s sequel or reflection or step-sibling. Another collection of traditional ballads, this one goes darker as Dylan, eyes glowing a demonic white, stirs balefully at a steaming cauldron of Mississippi blues, trying to suss out a curse or three for the Thane of Glamis and Cawdor. Blood and death and loneliness are the coin of this black realm. Let the artist give you a little taste of his thought process, directly from the album’s explanatory epistle:

BLOOD IN MY EYES is one of two songs done by the Mississippi Sheiks, a little known de facto group whom in their former glory must’ve been something to behold. rebellion against routine seems to be their strong theme. all their songs are raw to the bone & are faultlessly made for these modern times (the New Dark Ages) nothing effete about the Mississippi Sheiks.

You had me at ‘BLOOD IN MY EYES.’

The Playlist, part 2:

Oh Mercy

  • ‘The Man in the Long Black Coat’
  • ‘Political World’

Under the Red Sky

  • ‘2×2’
  • ‘God Knows’

Good as I Been to You

  • Froggy Went A-Courtin’

World Gone Wrong

  • ‘Stack a Lee’

Up next time:

As good a run as you might expect from the old jester.


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Virgindog
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October 29, 2025 11:23 am

I really like “Political World.” I was never a big fan so the others don’t float my boat but it’s good to see he’s remained creative for so long. 40 albums! That’s amazing.

rollerboogie
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October 29, 2025 11:24 am
Reply to  Virgindog

Your comment posted right as I was posting mine. We have similar thoughts on that song.

rollerboogie
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October 29, 2025 11:23 am

I was initially not highly motivated to check out this era of Dylan, but “Political World” had me intrigued so I listened to it, and read all the lyrics on line (Dylan’s annunciation can be hard to understand). It’s a one-chord song with lyrics that are both uniquely timeless and prescient. Could have been written today and totally would apply to the state of our world. It is very gloomy, and yet I take comfort in it, as I don’t feel so alone about how I feel these days. Is there anyone else that could have written anything like this? I say no.

I loved your references to artists with no late-stage catalogs. Seeing The Police and Sting’s post-band solo work mentioned in the same sentence was very triggering, as someone who made and kept a vow to never purchase any of Sting’s solo output after the demise of The Police. I do not consider those two worlds to intersect in any way and they need to be kept separate and seen as two completely different entities at all times.

The Beatles really do reflect the trajectory of rock/pop music throughout the whole of the 60s, looking at what music sounded like before the British Invasion, and then seeing how it progressed throughout the decade. Since they were pretty much at the forefront of those changes, it makes total sense. Lennon already saw them as becoming irrelevant toward the end of the decade. If they hadn’t broken up at that point, I don’t believe he would have lasted much longer. We would never have to watch them steadily decline into complete irrelevancy. The closest thing we have to get a glimpse of what it would be like is Paul’s Wings and solo discography. That’s just my opinion. Thank God mt doesn’t have a dislike button here. That did me in with my McCartney thoughts at the Gum back when you could down vote.

Last edited 22 days ago by rollerboogie
rollerboogie
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October 29, 2025 6:01 pm
Reply to  stobgopper

It’s fine. I can busy myself with rearranging my sock drawer that day.

mt58
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October 29, 2025 12:27 pm

Part one and two of Bob Dylan were more fun than just reading a Wikipedia page. Great insights and I feel like I’m caught up.

This is by no means delivered as an erstwhile assignment editor, but as a curious reader:
Any odds of late stage Paul McCartney making an appearance? The output may have been a little uneven, for the most part, it’s pretty astounding that he has been able to maintain as well as he has.
Just curious.

rollerboogie
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October 29, 2025 6:04 pm
Reply to  stobgopper

Flaming Lips would be an excellent candidate

JJ Live At Leeds
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October 29, 2025 2:13 pm
Reply to  mt58

For me Macca has got better with age. I find his 70s output patchy, varying from all time classic to all time low. The 80s was mostly the same except the highs were less frequent. Until 1989s Flowers In The Dirt. Since then the hits far outweigh the misses.

I was just thinking last week that its almost 5 years since McCartney III. Will we get anymore or is he done? It’d be a shame if that’s it but with everything he’s given us, I shouldn’t begrudge him taking it easier.

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