Late career is an amorphous idea.
For the purposes of this exercise, I draw the line in chalk:

Somewhere past where I think the peak occurred, but not deep enough into the post-Imperial phase to lose the thread.
By this criteria, I’ll mark Dylan’s late career as coming right after the holy trinity of Slow Train Coming, Saved, and Shot of Love:
Because of all the people you know, I’m the least prepared to discuss Scripture.
This puts us in the early ’80s, almost a decade out from Blood on the Tracks, with Bob navigating his 40s and more than 20 albums in. Still out there, far to the horizon, the odd bits, lullabies, traditional folk covers, the American Songbook, Christmas in the Heart.
Note: Included at the end of each blurb is a couplet from one of the respective album’s cuts, to remind us the man is a Nobel Laureate.

Infidels
1983
I thought—and probably wasn’t the only one—Knopfler was a good fit for producing this one, being ‘Dylanesque’ himself.
It didn’t work out.
‘Neighborhood Bully,’ while satisfyingly spry, espouses a Zionist viewpoint that lands even less comfortably today. OTOH, ‘Sweetheart Like You’ is a top-5 moment for me, and ‘Don’t Fall Apart on Me Again’ treads that pleasantly familiar ground of a forlorn man pleading with a woman to stay and save him as only Dylan and his writerly toolbox can.
No more mud cake creatures lying’ in your arms
What about that millionaire with the drumsticks in his pants?

Empire Burlesque
1985
The album cover makes Dylan look like a member of the band at the pool party in La La Land, giving the whole thing the unmistakable sheen of existing in its own era and nowhere else.
‘Tight Connection to My Heart’ has a Morrison knock-off vibe (albeit a good one). I like the idea of ‘When the Night Comes Falling From the Sky,’ but the album’s version is performed and produced as if a cover by a-ha. Better to seek out the one he cut with Roy Bittan and Steve Van Zandt. At least that sounds like a Springsteen cover (albeit a good one).
He bought the American dream but it put him in debt
Only game he could play was Russian roulette

Knocked Out Loaded
1986
A couple of things: was the title of this album a description of the circumstances of its making?
And then, much like the Beach Boys and Endless Summer, Biograph hit the market between the previous release and this one. Comparisons were made, mostly dire.
Luckily, oh so luckily, Dylan and Sam Shepard also birthed the magnificent ‘Brownsville Girl’ and it immediately entered the pantheon. In an alternative timeline, I’m making a playlist of Bob’s late career through the lens of his long-form epics. Otherwise, Little Junior Parker’s ‘You Wanna Ramble’ shakes with energy.
The only thing we knew for sure about Henry Porter
Is that his name wasn’t Henry Porter

Down in the Groove
1988
The title suggests we finally get a taste of reggae Dylan, as much as Street-Legal should have been a Lou Reed collab and Planet Waves his utopian manifesto.
But no.
Critical evaluation of this album is all over the place, if the place is ten feet underground: it’s been compared, unfavorably (!), to Self Portrait. Overly harsh, methinks.
We do get an interesting collection of side players. ‘Silvio,’ the lone single, rolls by on a silky (ahem) groove spiced with mandolin and Grateful Dead harmonies. ‘Death Is Not the End’ dirges along with hip hoppers Full Force providing angelic background vocals. A curio that’s slapdashed by an artist who slapdashes with the best of them.
The woman I love, she got two flat feet
Her knees knock together walking down the street
The Playlist (part 1):
Infidels
- Neighborhood Bully
- Union Sundown

Empire Burlesque
- Clean Cut Kid
- When the Night Comes Falling From the Sky

Knocked Out Loaded
- You Wanna Ramble
- Maybe Someday

Down in the Groove
- Death is Not the End
- Ugliest Girl in the World
- Silvio

Up next: throwbacks and curveballs and the ‘90s.


The only 80s Dylan I know even the slightest is the part you skipped, which to be fair, most people do. His 3 albums during his born-again phase tend to be dismissed. I don’t know many songs from them, just a few, but there is one that I’ve seen ranked pretty high more than once on ” Greatest Dylan songs of all-time” lists, and that would be “Every Grain of Sand”. It’s stunning.
I am right there with you on all parts of this comment. EGOS is all-time for me.
Like rollerboogie, I don’t know much about 80s Dylan, so thanks for curating it down to the good stuff. I don’t I’d bother sorting through his full albums, so this makes it easier. Rocking “Neighborhood Bully” now….
I knew Dylan was on some kind of pilgrimage during these years, trying on different costumes as musical styles came and went. His idiosyncratic responses to these changes weren’t always successful, but they were interesting. Or ‘interesting.’
I missed 80s Dylan. I knew who he was but that was as some old irrelevant guy long past his best.
There was The Travelling Wilburys but the irreverence of Smash Hits treated them as further proof that he was past it and needed the company of some other old guys to make something half decent.
It wasn’t til the mid 90s that I got a handle on him. Everything I read said stay away from 80s Dylan, at least until Oh Mercy. Advice that I’ve continued to follow.
I do like the line;
The only thing we knew for sure about Henry Porter is that his name wasn’t Henry Porter.
Sounds like the start of an intriguing pot boiler about a man who turns up in town and isn’t what he seems.
This is the first time I’ve ever heard anything that cynical said about The Travelling Wilburys. Here, it was mostly seen as just a bunch of the biggest rock stars just having a good time together as friends and some great music came out of it.
At least that’s how I remember it.
It wasn’t cynicism. Smash Hits in its 1980s glory years was all about treating pop stars with a healthy dose of irreverence and all the funnier for it It was cheeky without being rude.
‘Brownsville Girl’ is epic Dylan. And with epic Dylan, you get a lot of scratching-one’s-head moments, half of them profound, the others too obscure or ridiculous (or both!) to think about.
I like the music video for “Tight Connection to my Heart”. It’s like his “Dancing in the Dark”, a song he hoped would connect with the MTV generation. Dylan’s agent must’ve got down on his hands and knees, begging him to do it. His facial expressions throughout the song’s entire running time tells me so.
Dylan’s facial expressions span the range from pissed to disinterest, it seems. Though I do enjoy ‘Tight Connection…’ It’s on my more prosaic ‘Best of Dylan’ playlist.