The 25 Greatest Dylan Songs of The Past 20 Years

"You think I'm over the hill
You think I'm past my prime
Let me see what you got
We can have a whoppin' good time"

      - Bob Dylan, "Spirit On The Water"

Some might say that Bob Dylan is way past his prime and that all of his best work is well behind him, but anyone who would say such a thing clearly doesn't know much about good music. Either that or they've just been awoken from a 20-year-long coma.

"What I'm doing now, its a whole other thing. We're not playing rock music. It's not a hard sound. I don't know what it is." That's a quote from Dylan during the Highway 61 Revisited sessions back in 1965, but it just as easily could apply to the brilliant work of his Second Coming. That is, his resilient resurgence of the past 20 years, starting with the release of Oh Mercy in 1989 and continuing right on up until this fall and the release of Tell Tale Signs, the latest installment of the ongoing Bootleg Series.

During this remarkable late-career renaissance Bob has created a body of work that rivals just about any other in popular music over the past 50 years. There have been four classic albums of original material, two excellent albums of traditional folk blues covers, and some truly amazing soundtrack work.

And, as if that wasn't enough, many of the tracks that remained in the vaults until the release of Tell Tale Signs this year turned out to be as good as, or better than, any of the released material.

Furthermore, in all this time - two full decades - the man has only released one album that wasn't up to this new standard of near-perfection.

So, what then are the best songs of this glorious Second Coming of Bob?

At first I decided to make this a list of the best 20 songs of the past 20 years, but that was simply too difficult, so instead I ended up going with a Top 25. Deciding on just 25 tracks from this stunning body of work was not much easier, however, but I've given it my best shot.

And so, without any further ado, here they are, my Top 25 Bob Dylan Songs of The Past 20 Years:

#1. Mississippi
Although I do love 2001's Love & Theft, I simply don't find the individual songs anywhere near as appealing as those on the albums that both preceded and followed it, Time Out Of Mind (1997) and Modern Times (2006). That is, except for this absolute classic (and one other - see below). It's not only my favorite track on the album, it's also my favorite Dylan song of the past two, if not three, decades. In the fourth verse, Bob himself inadvertently sums up just what he's put into this mesmerizing masterpiece of a song:

"All my powers of expression and thoughts so sublime".

I was tempted to list the Love & Theft full-band version of this classic and the beautiful, quiet, solo version from the Time Out Of Mind sessions (which kicks off disc one of the Tell Tale Signs album) as my #1 and #2 songs on this list, as they are pretty well two completely different - and equally magnificent - songs. But, in order to make room for one more modern-era Bob classic, I've combined both versions into my number one pick. But both must be heard.

Listen here (solo) and here (full band)

#2. Red River Shore
An incredibly beautiful song from the Time Out Of Mind sessions that Bob incomprehensibly decided to leave off the album (and unreleased for the next 11 years), despite the fact that it's one of his greatest songs ever.

And here's the thing: Time Out Of Mind is an absolute classic BUT, unbelievably, the two greatest songs from those sessions were both rejected by Bob in all his infuriating, mindboggling, enigmatic genius. He made us wait a mere 5 years to finally hear "Mississippi", but a ridiculous 11 years for this masterpiece.

Listen here

#3. Tryin' To Get To Heaven
A beautiful melancholy classic from an album full of beautiful melancholy classics. "Highlands" may be the most spellbinding track on Time Out Of Mind, but this one is my favorite.

Listen here

#4. 'Cross The Green Mountain
Lyrically one of Bob's greatest songs ever... and we're talking about the guy who wrote "Desolation Row", "Visions Of Johanna" and "Idiot Wind". A magnificent song off of the Gods and Generals Soundtrack... which attempts to sum up the horror and tragedy of the Civil War in just eight glorious, mournful minutes.

Listen here

#5. Workingman's Blues #2
Simply majestic! Perhaps some would say that "Ain't Talkin'" is the centerpiece of Modern Times, but to my mind this is the outstanding track on that outstanding album.

Listen here

#6. Highlands
Sixteen and a half minutes of bliss. And one of the funniest songs in late-period Bob's repertoire, particularly noticeable on an album as melancholy as Time Out Of Mind. Actually, to be more precise, part of the song is quite funny, the rest is, well, rather melancholy.

Interestingly, a few years after this was released Bob bought an estate in the Scottish highlands where his heart, as he makes quite clear here, already was back in 1997.

Listen here

#7. Born In Time
My favorite song on my least favorite Bob Dylan album of the past two decades, Under The Red Sky (1990). The original version, recorded at the Oh Mercy (1989) sessions a year earlier and finally released on Tell Tale Signs, is even better.

Listen to the second unreleased version from Tell Tale Signs here

#8. Standing In The Doorway
Another sad, melancholy song from Time Out of Mind, this time about lost love. Bob at his world-weary best. Not since Nick Drake - and Bob's own Blood On The Tracks - has such mournful sadness sounded so incredibly beautiful.


Listen here

#9. Dignity
Another Oh Mercy outtake, finally released in 1994. And, again, better than most of the songs that actually made it onto that album. Lyrically one of Bob's greatest triumphs. The bouncy upbeat version as well as the solo piano version that appear on Tell Tale Times are both particularly great. Too bad the solo piano version ends abruptly mid-song. The live version that appears on 1995's MTV Unplugged is pretty damn great as well. Only Dylan - or perhaps Cohen - could have written this poetic masterwork.

Listen to the solo piano version here

#10. Not Dark Yet
Another track from 1997's Time Out Of Mind and the most glaring example of Bob seemingly coming to grips with his own mortality. Though he denied it was about that, of course.

As the song says: "Behind every beautiful thing there's been some kind of pain".

On hearing this track upon its release - with the knowledge of Bob's near-brush with death soon after the album's completion - it sure had an eerie feeling of premonition (he had a heart infection called pericarditis, which was brought on by something called histoplasmosis - thankfully he made a full recovery).

Listen here

#11. Most of The Time
I always liked this song on Oh Mercy, but the stripped-down version that was just released on Tell Tale Signs is a revelation. Another bizarre track selection choice: The unreleased version is so clearly superior to the one he chose for the album. Is it intentional? Perhaps Bob just keeps the best songs and versions for his friends and family to enjoy for the first few years after they've been recorded. I'm thinking it's some sort of revenge against the insane fans who went through his garbage and staked out his home all those years ago. But why do the rest of us have to pay so dearly?

Listen to the Tell Tale Signs version here

#12. Make You Feel My Love
A love song - yes, a love song - on Time Out Of Mind. Thematically it may seem a bit out of place on an album of songs about impending mortality and past heartbreak, but, in fact, it fits in perfectly.

Listen here

#13. Huck's Tune
A beautiful song hidden away on the soundtrack to the largely-unseen Drew Barrymore-Eric Bana film, Lucky You. Luckily now available to all on Tell Tale Signs.

Listen here

#14. Ain't Talkin'
Never before has such an epic tale of vengeance - or maybe I should say quest for vengeance - sounded so beautiful. Many would say that this is the centerpiece of 2006's Modern Times, though some, like myself, would say that honor lies with "Workingman's Blues #2". Either way, a classic track. Musically, I prefer the version on Tell Tale Signs.

Listen to the Modern Times version here

#15. Everything Is Broken
Again, the version on Tell Tale Signs trumps the one released on Oh Mercy. Always great to hear different versions, for the different lyrics alone, which in this case are almost completely transformed.

Listen to the Tell Tale Signs version here

#16. Can't Escape From You
Another gem - this one from 2005 - left unreleased until late-2008, when it finally appeared on Tell Tale Signs.

Listen here

#17. Nettie Moore
A blues song if ever one was written. Not chord-wise perhaps, but sentiment-wise, absolutely. Another great track from Modern Times.

Listen here

#18. Spirit On The Water
A jazz-infused upbeat number from Modern Times.

Listen here

#19. Summer Days
Good old-time music. Like most of the songs on his last couple of studio albums (Love & Theft and Modern Times), this song from Love & Theft sounds like it could have been recorded back in 1952. But, unlike so many of the songs on Time Out Of Mind, the album that preceded it, Bob is at his most upbeat and humorous here. Melancholy is nowhere to be found in this number.

Listen here

#20. Things Have Changed
Bob's Oscar-winning track from the Michael Douglas-Tobey Maguire film Wonder Boys, in which Bob famously sings "I used to care, but things have changed". Nothing, of course, could be further from the truth, at least when you compare 1987 Bob to modern-day Bob.

Listen here

#21. Someday Baby

A great tune, both the more upbeat version on Modern Times and the slower, quieter one that appears on Tell Tale Signs.

Listen to the Tell Tale Signs version here and the Modern Times version here

#22. Marchin' To The City
Yet another terrific tune from those amazing Daniel Lanois-produced Time Out Of Mind sessions. The slow bluesy version on disc one of Tell Tale Signs is the definitive version.

Listen here

#23. When the Deal Goes Down

Another gorgeous track from Modern Times.

Listen here

#24. Series of Dreams
Another Oh Mercy outtake. And another poetic masterpiece. I prefer the more sparse version on Tell Tale Signs to the version released The Bootleg Series Vol 1-3 back in 1991.

Listen and watch the great music video for the song here

#25. Heartland
Bob's duet with Willie Nelson (co-written together as well) from Willie's 1993 album Across The Borderline. Originally written about the plight of American family-farmers in the age of the corporate farm, the song remains quite topical today, and not just when it comes to farmers:

"There's a home place under fire tonight in the Heartland
And the bankers are takin' my home and my land from me

My American dream
Fell apart at the seams.
You tell me what it means,
You tell me what it means"

Listen here

Special Mention:

Although I haven't placed them in the above list due to the fact that they're both covers of old traditional tunes, two of my favorite Bob songs of the past 20 years are the two upbeat and incredibly-spontaneous-feeling tunes from the 2003 soundtrack to Masked & Anonymous: "Diamond Joe" (not to be confused with the completely different song of the exact same name that appears on Good As I Been To You) and "Dixie". Rarely has Dylan sounded this upbeat and joyful in recent years, particularly on "Diamond Joe". I love these two tracks!

Don't get me wrong, I love Bob's two collections of traditional folk and blues songs, Good As I Been To You (1992) and World Gone Wrong (1993), and his interpretations of songs like "Hard Times", "Froggie Went A-Courtin'", "You're Gonna Quit Me", "Arthur McBride", "World Gone Wrong" and "Delia" are all unquestionably revelatory and sublime. It's just that "Diamond Joe" and "Dixie" feel especially spontaneous, exuberant and joyful.

Listen to "Diamond Joe" here and "Dixie" here

And just in case you're interested in which song just barely missed the cut, the last song I removed from my short-list was "Til I Fell In Love With You". Listen here

Missing Tunes

So there you have it, my picks for the 25 greatest late-era Dylan tracks. All classics. Heavily drawn from the 1997 sessions for Time Out Of Mind, but covering the entire stunning two-decade period since 1989. Of particular note is the fact that 13 of these 25 songs came out of sessions produced by the great Daniel Lanois.

Aside from highlighting the greatness of those sessions, however, this list also makes one other thing quite glaringly apparent and that's just how essential the new album, Tell Tale Signs, really is. If you haven't already got it, go buy it now.

Finally, I should say that it's obvious that many great tunes, including, I'm sure, some people's favorites, are missing from this list, but, hey, I only got to pick 25... and I'm sticking with them.

Mike Cowie (Oredakedo)
Saturday, November 29th, 2008


Postscript posted on November 30th, 2008: If we were to extend the period under consideration back a few more months to include late-1988, I'd most definitely have Bob's great Traveling Wilburys song, "Tweeter and the Monkey Man" - that hilarious Bruce Springsteen parody/homage - on this list as well.  Listen here


Postscript posted on January 22nd, 2009: After further reflection - and two more full months of listening to Tell Tale Signs - I've now got to agree with some of those who left comments below that both "Ring Them Bells" and "Can't Wait" probably do, in fact, belong on this list. The versions of these two songs that appear on Tell Tale Signs are indeed revelations.



To read my previous piece about Bob click here: You Got A Lotta Nerve: Dylan Named One of The Greatest Singers of All Time


And to read my two - yes two - recent rave reviews of Bob's new album, Tell Tale Signs, click here: Bob's Back: Tell Tale Signs of Joy... and A Complete Lack of Judgement


And here: Tell Tale Signs of Genius: Dylan's Best Album of The Past 20 Years? (Rave #2)


Or check out this piece about another musical icon: The Neil Young Rave: A Film, Two Albums and Incarnations For Everyone


And to read my piece on Bob, Neil and Joni click here: Talkin' Prairie Triangle of Inspiration (A.K.A. Bob Dylan, Neil Young and Joni Mitchell Make Their Great Escape)


And for much more on all things Dylan click here: The Bob (as in Dylan)


Or for more on other artists and albums click here: Music Homepage


Or here: Music: Album and Concert Raves


MikesAndDislikes Home


Top 25

I think "If You Belonged to Me" (Wilburys) is a great song. It would be on my list. Few other quibbles, though, good list. I'd put "Standing in the Doorway" even higher than you do.

I agree "Cold Irons Bound"

I agree "Cold Irons Bound" should be here, particularly because of how well it comes off live. And "I Feel A Change Comin' On" is a classic.

"I Feel A Change Comin' On"

I agree that "I Feel A Change Comin' On" is an awesome tune, but this list was compiled back in 2008, before the album "Together Through Life" was released. Mike Cowie

Everything is Broken?

Good list, and I'd agree with most of the choices (though probably not the order). Can't understand how you could choose Everything Is Broken over either Ring Them Bells, Shooting Star or Man In The Long Black Coat, though. It will be interesting to see if any of the songs from the new album displace any of the ones on your list.

No Way

my list would replace: Born in Time Make You Feel My Love Everything is Broken Can't Escape From You Someday Baby Heartland with the obviously superior: Ring Them Bells High Water Cold Irons Bound Can't Wait Tell Ol' Bill Man in the Long Black Coat


erm... Where is Masters of War ?

Wrong Era

"Masters of War" is from 1963. This list covers the years 1989-2008.



Your list is almost perfect... But IMO Cold Irons Bound deserves a place in that! Particularly two live versions: on Masked and Anonymous and on Tell Tale signs live. Brunocat

Missed a couple

High Water is the best song on Love & Theft, followed by Po' Boy. Sorry you didn't include them on your list. (BTW, I agree with Mississippi at or near the top of the list. However, having heard the version(s) on Tell Tale Signs, particularly the first one, it's clear that the L&T version, while great, doesn't hold a candle) Ring Them Bells should also be in the top 25.

25 Greatest Dylan Songs of The Past 20 Years

My Top 25: 1 Mississippi ("Love & Theft") 2 Not Dark Yet 3 Workingman Blues # 2 4 Red River Shore (Tell Tale Signs 1) 5 Most Of The Time (Tell Tale Signs 3) 6 Floater 7 Cross The Green Mountain 8 Man In The Long Black Coat 9 Standing In The Doorway 10 Nettie Moore 11 Ain't Talking 12 Born In Time (Tell Tale Signs 3) 13 Tryin' To Get To Heaven 14 Can't Wait (Tell Tale Signs 3) 15 Dignity 16 Marchin' To The City 17 Handy Dandy 18 Series Of Dreams (Tell Tale Signs 2) 19 Things Have Changed (Tell Tale Signs 3) 20 Spirit On The Water 21 Huck's Tune 22 Tell Ol' Bill (North Country version) 23 High Water 24 Cat's In The Well 25 Someday Baby (Tell Tale Signs 1)

Top 25

Handy Dandy should be in!

The 25 Greatest Dylan Songs of The Past 20 Years

Nice list but I do not agree. Everything Is Broken, Heartland, When The Deal Goes Down, Can't Escape From You and Make You Feel My Love are all minor works (i.m.o.). I miss Man In The Long Black Coat, High Water, Floater, Po' Boy and Sugar Babe.

Nice! Best "Not Dark Yet," . . .

. . . however, would have to be, no dissent, no argument, no animadversion or quibbling or quizzling, that from the summer of 1999 "club tour," specifically, St. Andrews Hall in Detroit. Just breathtaking.

Um, you forgot a few

No "High Water" "Po' Boy" or Lonesome Day Blues"? Listen to "Love and Theft" until you repent.

Just one song missing

Ring Them Bells

and one more

Million Miles!


Hey Mike, Back when we used to hang out briefly in the late 80s, I was fully immersed in Dylan and had no idea you were a fan. I've enjoyed reading your musings of late (via Expecting Rain) and feel compelled to comment on your choices. Firstly, I completely agree about "Cross the Green Mountain" - one of my top 10 dylan songs ever. Brilliant lyrics aside, the vocals are so evocative they carry you away. I've learned it on guitar; now I just need another 30 years of hard living to rough up my voice. A bit surprised that you chose "Make You feel My Love" which I've always thought was a bit of a throwaway. I give you a pass on not picking more from "Good as I Been" and "WGW" since they were covers, but both "Jim Jones" and "Canadee-i-o" feature very strong vocals and guitar playing. I've had the Lanois-produced "Born in Time" for about 15 years, but it was on a bootleg cassette and it's SO nice to have a good digital version. It's too bad Don Was crapped all over the material from "Under the Red Sky" because there are some gems buried under the mix, including "Cat's in the Well" and "God Knows." Finally, I want to say how refreshing it is to read someone with the same amount of respect I have for the recent material. There are still so many people - even some who should know better - who think Dylan's 60s work is where it starts and ends. I caught him at Save-On last month, and was lucky enough to have front-row center seats. I hadn't seen him as buoyant on stage in about 20 years - he was practically dancing. BTW were you at the Rage show in 98? He did a version of Lightfoot's "I'm Not Supposed to Care" that I'd love to hear again, if you ever come across it. Jim Martell (Greg Bryan's buddy)

Bob's top 25

Agree with all, except Everything is Broken instead of the new version of Can't Wait? For me, the biggest revelation on Tell Tale Signs.


I like your choices. Mississippi is such a great song, interesting to see more people join our view. The live versions are often revealing as he tries to get to the heart of the song. Doing a music news site at - visit if you'd like. Cheers.

Your Top 20

Pretty much agree with all of those choices there.

Agree with the top 2

Agree with the top 2, agree with Highlands and Dignity being in the top 10. Agree with the acoustic Most Of The Time. Don't agree with Cross The Green Mountain or anything off Modern Times. God Knows, Cats In The Well, Shooting Star, Love Sick and Cold Irons Bound I think should be in there.