What are the most harmonically complex songs of Bob Dylan?, I asked in BobDylan SubReddit. I got many interesting answers…

To Fall in Love With You, which was never really finished, has an extended progression which takes a long long time to get to the key chord.
I’ve always found On a Rainy Afternoon to have a very elegant chord progression, though it wasn’t ever completed. Very simple in the beginning, but the resolution of the progression gets much more involved.
Lay Lady Lay actually has kind of a weird chord progression, which I just realized yesterday.
Nashville Skyline has soooo many amazing changes. Among my top 5 faves
I threw it all away has some funky changes as well now that I think of it
I’m very partial to Tell Me it Isn’t True
I was going to say Oh Sister but I just remembered I thought the other day that it sounded like Knockin on Heavens Door … not Lay Lady Lay … so I am not helpful lol but I want to see if someone knows!
I think it’s similar to All Along the Watchtower, but not exactly the same if I’m remembering correctly
Frankie Lee And Judas Priest – FLJP is G with a capo on the 7th fret (so effectively C), but it’s G, Bm, Am, G (I iii ii) whereas LLL is A, C#m, G, Bm (I iii bVII ii). The G (bVII) in LLL gives it a unique characteristic not present in FLJP. It also gives it a chromatically descending bassline – A – G# – G – F#. I can’t recall any other BD songs with a chromatically descending bassline like that (though I suspect there are some bridges which do it.
House of the resizing sun and death of emmit till have a C/G D/F# F bassline which gets close and simple twist of fate has E, EMaj7, E7, A which gets close but it’s not the bassline so much.
The rolling thunder review SToF were G, Bm, G7, C which is the closest song, in spirit, to LLL I can think of offhand.
Make You feel My Love also has a rather nice chromatically descending bassline.
There is an interesting ascending bassline in the pre-chorus of Too Much of Nothing.
Ballad of a Thin Man has another chromatic descending bassline in the start of the verse.
There it is! I really need to listen to JWH more I’m pretty unfamiliar with it compared to the rest of 60s/70s work
I will say that Dylan and folk music in general though is not where you go for harmonic complexity. If you compare Dylan and, say, Steely Dan or queen by that metric, he’s pretty primitive. But he does have some deceptively great melodies and chord progressions, as evidenced by the number of artists who want to cover his work. And as for that one-of-a-kind voice and those lyrics, well, we all know about that.
One of the first ones that comes to mind is Forever Young Fast Version
Dear Landlord and In the Garden have some interesting stuff going on. A lot of the gospel songs have chord progressions that vary from the “standard” folk patterns.
Black Rider, In the Garden, Dear Landlord.
Just listening to In the Garden, wow, these constant stairs-like modulations (transpositions?) are amazing!
Moonlight.
I Contain Multitudes has some pretty complex chords
In search of little Sadie (or whichever of the two plays first on self portrait) has a strange chromatic chord progression that’s very unusual, and it’s literally Dylan reharmonizing an old folk song so that in itself is pretty interesting to me
Dear Landlord. And if I hear it right, blind willie mctell has an interesting chord progression too
Tears of Rage comes to mind, its sooo pretty and a really unique structure. Richard Manuel composed the music to Bob’s words on that one though.
On A Night Like This uses an Am/F# (F# half-diminished)
“In the Garden” is probably the answer, as it modulates four or five times in the space of a verse while the melody employs a couple scales.
“Dear Landlord” modulates all over the place as well
“Black Rider” is a truly novel progression and the final contender for most harmonically advanced song with its chromaticism and modulations.
“Covenant Woman”, “Moonlight”, “I Contain Multitudes”, “Make You Feel My Love”, “Too Much of Nothing”, “Ring Them Bells” all deserve honorable mention but are not as complex as the three listed at the top.
‘Tonight I’ll Be Staying Here With You’ has some pretty interesting stuff going on. The verses are a pretty straight forward G-C thing, but then in the B-section the C swaps to a minor chord, and all of a sudden there’s an A-flat major thrown in there which transitions back to C-maj and then A-min.
Mama, You Been On My Mind – I believe it is in the key of C and uses an E7, D7, and G#dim7.
Gates of eden really stands out, because most of his early stuff is very simple chord wise. But here he modulated between g major and c major all the time. And then that Bb major comes out of nowhere and it sounds just great. That Bb to C to G is actually kind of an early punk chord progression.
This Wheel’s on Fire has more chords than most Dylan tunes and a diminished chord in there as well, which he doesn’t use a lot. Rick Danko is credited for composing the music with Dylans lyrics.
Baby let me follow you down
“It’s all over now baby blue” which is in C, uses an E major on the transition, which is and sounds interesting
In thE Garden, Dear Landlord, Moonlight, and Black Rider are the ones I see most commonly mentioned here
I’ve seen people post before that In the Garden is probably his most complex song harmonically which I would have to agree with.