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100 Greatest Bob Dylan Songs- 1. Like a Rolling Stone 2. Tangled Up in Blue, Congratulations to Bonzai, winner of the contest (1 Viewer)

Of course I'm chimin' in. #1?

I also loved especially loved the last lyrics too. Very feminine, I thought. 

Did not like the Tedeschi version. Too plodding. 

 
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timschochet said:
6. “Idiot Wind” (1975, from Blood On the Tracks

https://youtu.be/Ex05XUddWMk

The meanest, nastiest  song ever written? For my money it’s only close competitor is Queen’s “Death on Two Legs” (which ironically was written the same year.) But on “Idiot Wind” Dylan doesn’t hold back: 

You hurt the ones that I love best and cover up the truth with lies, one day you’ll be in the ditch, Flies buzzin’ around your eyes, blood on your saddle 

Damn. Or how about 

You’ll never know the the hurt I suffered, nor the pain I rise above. 

And most of all the last line of the chorus: 

You’re an idiot babe, it’s a wonder that you still know how to breathe. 

This is Bob Dylan using his lyrics as a sharp knife, stabbing someone in the heart


my choice for #1 

(bolded completes the lyric chain, and is too vicious to leave off).

 
4. “Just Like a Woman” (1966, from Blonde on Blonde

https://youtu.be/dRLXZVojdhQ

The lyrics are so deceptively simple, and that’s what make them so brilliant: 

Nobody has to guess that baby can’t be blessed, till she finally sees that she’s like all the rest 

and 

Ain’t it clear that I just can’t fit 

Yes, I believe that it’s time for us to quit 

When we meet again, introduced as friends, please don’t let on that you knew me when I was hungry and it was your world 

As for the chorus, in terms of songwriting it was nothing short of revolutionary. Nobody wrote songs at the time about mature women and their needs, physical and emotional (actually nobody really wrote about women at all, at its still rare for a male artist to do so.) The line “she breaks like a little girl” has long been both praised and criticized by different sets of feminists. But I don’t think Dylan was out to make some larger statement here; he was trying to be poetic and introspective from personal experience. That’s true for a lot of his best songs and he rarely achieved success greater than in this one. 

Covers Of all the fine versions I’ve heard of this song, none is better than Richie Havens, first recorded in the same year (1966) as the original recording. I’ve not in love with the instrumentation but Haven’s raw vocals are so full of emotion that they make up for everything else: 

https://youtu.be/-9pgx3zSrDQ

 
3. "It's Alright, Ma (I'm Only Bleeding)" (1965, from Bringing It All Back Home)

https://www.youtube.com/watch?v=mYajHZ4QUVM

Greatest song lyrics ever? Consider:

Darkness at the break of noon
Shadows even the silver spoon
The handmade blade, the child's balloon
Eclipses both the sun and moon
To understand you know too soon
There is no sense in trying.
Pointed threats, they bluff with scorn
Suicide remarks are torn
From the fool's gold mouthpiece
The hollow horn plays wasted words
Proves to warn
That he not busy being born
Is busy dying.
Temptation's page flies out the door
You follow, find yourself at war
Watch waterfalls of pity roar
You feel to moan but unlike before
You discover
That you'd just be
One more person crying.
So don't fear if you hear
A foreign sound to your ear
It's alright, Ma, I'm only sighing.


And that's just the first verse. There's 3 more just as good. As good as any poetry you're ever going to read on the written page. So the only question is, why is this #3 and not the clear #1?

Melody is the only reason. Greatest lyrics ever but the melody is close to traditional folk, doesn't go anywhere. In terms of popular music it's not a complete song; it's certainly not something you're going to sing along to. I'm pretty certain it never appeared on the radio of it's own accord. I'm even more certain that nobody who is not a Bob Dylan fan has ever even heard it. (Though some years ago Dylan quoted some of the lines on Sixty Minutes with a marveled look on his face as if to say, "Can you believe I actually wrote this?")

The most famous line is in the 1st verse: "He not busy being born is busy dying." However, my personal favorite lines, in light of current events, is this:

While preachers preach of evil fates
Teachers teach that knowledge waits
Can lead to hundred-dollar plates
Goodness hides behind its gates
But even the president of the United States
Sometimes must have
To stand naked.


Covers Not really, no. This is a really hard song to sing and play. The Byrds tried to do it, its their worst Dylan cover and I won't link it here. Nobody else notable has even dared to give it a go.

 
2. “Tangled Up in Blue” (1975, from Blood On the Tracks

https://youtu.be/YwSZvHqf9qM

1. “Like a Rolling Stone” (1965, from Highway 61 Revisited

https://youtu.be/IwOfCgkyEj0

Time to wrap this up. The top 2 songs are pretty anticlimactic. Two of the greatest songs ever written and I don’t have much further to add to that. I also don’t have covers to present (even though there’s one I really like by the Indigo Girls of Tangled Up in Blue; the original songs are too good to consider them.) 

 
I'll take a stab:

Like a Rolling Stone 
Tangled Up in Blue 
Don’t Think Twice, it’s Alright 
It’s Alright Ma (I’m Only Bleeding) 
It's All Over Now, Baby Blue
A Hard Rain's A-Gonna Fall
The Times They Are a’ Changin’
Visions Of Johanna
Desolation Row 
Blowin' In The Wind
Congratulations to @Bonzai, winner of the contest with 6 songs in the top 10. You have great taste! Please pick your charity so that I can make a donation. Thanks to everyone who participated. 

And thanks to everyone who bothered to read this. I’m thinking about doing another one for Paul Simon. Should I? Let me know. 

 
2. “Tangled Up in Blue” (1975, from Blood On the Tracks

https://youtu.be/YwSZvHqf9qM

1. “Like a Rolling Stone” (1965, from Highway 61 Revisited

https://youtu.be/IwOfCgkyEj0

Time to wrap this up. The top 2 songs are pretty anticlimactic. Two of the greatest songs ever written and I don’t have much further to add to that. I also don’t have covers to present (even though there’s one I really like by the Indigo Girls of Tangled Up in Blue; the original songs are too good to consider them.) 
Thanks for a great thread, Tim.  Fwiw, I thought the Jerry Garcia Band did a respectable cover of Tangled Up in Blue.  

 
timschochet said:
And thanks to everyone who bothered to read this. I’m thinking about doing another one for Paul Simon. Should I? Let me know. 
Does it include Garfunkel? If not, I can't see a hundred Paul Simon solo songs, thought that may be just me. 

 
pretty compelling breakdown/endorsement of "Blue" here ... but i tend to agree with your take. 
Huh. Perhaps this, then. A great song for sure. Great clip. I'm through about nine minutes of it. The interesting part about the use of time and the verses and the subject matter is cool, especially the broad strokes of 3-6 and the minutiae of 4-5. I think pointing out its intent in repetitiveness is important to the song, one that I might have just taken as droning on along the same lines. What I had identified from the naked ear to soul as, "Will this ever finish?" takes on new meaning after watching that. 

 
Huh. Perhaps this, then. A great song for sure. Great clip. I'm through about nine minutes of it. The interesting part about the use of time and the verses and the subject matter is cool, especially the broad strokes of 3-6 and the minutiae of 4-5. I think pointing out its intent in repetitiveness is important to the song, one that I might have just taken as droning on along the same lines. What I had identified from the naked ear to soul as, "Will this ever finish?" takes on new meaning after watching that. 
i recall earlier in the thread when "Hurricane" was discussed ... i believe a lack of subtlety was referenced as to why it didn't place higher ... now, to me, the visceral chugging along of that song, and it's sledgehammer narrative, drops my jaw every time, still some 43 or so years after first hearing it ... it ####in' blisters and rocks and careens along at a breakneck pace.  

"Blue" is quite the opposite in structure and delivery, as we saw so painstakingly extrapolated in that clip ... and it all begins to win me over so much more when seen/heard thru that prism ... though i still prefer "Hurricane" and "Idiot" and "Changing of the Guards" more, as i find them to be a more biting Bob, which is the Dylan i most love and dedicate listening time to.  

 
Apple Jack said:
Au contraire

Love Jerry's backing vocals on a couple last lines of verses...they all play on the pennywhistle, you can hear them blow...

Einstein disguised as Robin Hood
With his memories in a trunk
Passed this way an hour ago
With his friend a jealous monk
And he looked so immaculately frightful
As he bummed a cigarette
And went off sniffing drainpipes
And reciting the alphabet
You wouldn't think to look at him
But he was famous long ago
For playing electric violin on Desolation Row
Was at that show. 

 
timschochet said:
Congratulations to @Bonzai, winner of the contest with 6 songs in the top 10. You have great taste! Please pick your charity so that I can make a donation. Thanks to everyone who participated. 

And thanks to everyone who bothered to read this. I’m thinking about doing another one for Paul Simon. Should I? Let me know. 
:bowtie:

Thanks for doing this. Great job! It was fun to follow along.

As for my charity, I'm going to go with The Jed Foundation.

The Jed Foundation

Every four seconds, someone loses their life to suicide. Suicide prevention is also the theme of this year’s World Mental Health Day. If you want to help tackling this issue, you can donate to The Jed Foundation, a non-profit organization working to prevent suicide for American teens and young adults. Founded in 2000 by Phil and Donna Satow, a couple who lost their youngest son to suicide, the organization has been rated 4-stars (the highest rating) by Charity Navigator for its financial health, accountability and transparency. 

 
:bowtie:

Thanks for doing this. Great job! It was fun to follow along.

As for my charity, I'm going to go with The Jed Foundation.

The Jed Foundation

Every four seconds, someone loses their life to suicide. Suicide prevention is also the theme of this year’s World Mental Health Day. If you want to help tackling this issue, you can donate to The Jed Foundation, a non-profit organization working to prevent suicide for American teens and young adults. Founded in 2000 by Phil and Donna Satow, a couple who lost their youngest son to suicide, the organization has been rated 4-stars (the highest rating) by Charity Navigator for its financial health, accountability and transparency. 
Done. Sounds like a great organization so I’m happy to do it. 

 
Can we get the top 100 put in the OP some high ranked songs I’m not familiar with that I’d like to come back and reference 

 
Maybe I overlooked it, but did neither Watching the River Flow nor Lay Down Your Weary Tune make your top 100???

 
100 countdown listed in the OP

This was fun to read through the last couple days. Completely missed it the first time around.

I know why....it was the darkest time in my life. I was in an deep abyss, and could barely function. I had neglected my mental health for decades - combat PTSD and severe depression. WRT the latter, my evaluation included several different tests, and I was on the extreme end of the spectrum for a good long while. Like barely get out of bed or function level of darkness.

I bring that up bc many months later - whilst in a 5 day, 30 hours per week outpatient program through the VA, which lasted two full years - at the encouragement of my music therapist, I embarked on a review of the entire discography. I analyzed and wrote about every composition Bob Dylan ever published. I would share my research (& a song of the day) with my fellow veterans. It was very cathartic.

(each day concluded with an hour of veterans sharing music with each other & what the song means to them)

Music therapy was one of a dozen classes I was attending, but along with mindfulness meditation to start off, the only one I did daily. I researched, wrote, and introduced a Dylan song every weekday for 104 weeks, less holidays. Might have skipped a few basement tapes dittys or a couple other obscure ones but basically covered everything he ever released.

Drove the other veterans bonkers but don't you understand, its not my problem?

Wouldn't say Dylan is especially effective as a directed therapeutic method, but it gave me some measure of joy each day. At the time, that was in short supply, so there is that.

***************

Same same for @Eephus and the epic Walks with Bosley & Bob thread. Didn't catch it the first time, but thoroughly enjoyed reading your wonderfully crafted review of all his albums recently. In particular, enjoyed the concluding paragraph of each post. In fact, so much that I had to go find the Sinatra thread bc I just had to know how the end was for the old boy. Not ashamed to say I cried for that black dog on more than one occasion.

You're a mensch. Thank you for taking us on that journey.
 
It's kinda silly that not only did I search and find a Bob Dylan thread, but we have a countdown. Love this site. Bob Dylan's prime was really before my time where I enjoyed music. I never listened to him. I mean at all. I jumped into him a few months ago and the rabbit hole has been wonderful. Not his later stuff though. As he got older it just got bad, but Dylan music from the 60s and 70s was just good stuff. His older stuff just grabs you.
 
I know this will seem sacrilegious, but I actually had the chance to see Dylan 30 years ago for free, went for awhile, and didn't stay for the whole show. The show was at Toad's Place in New Haven, and our college radio station (of which I was a DJ and production manager) always got tickets for shows at Toad's.

I am not a huge Dylan fan as something about his voice doesn't do it for me. Great song writer, but not a great singer IMO. IIRC, I stayed for the first two sets . . . but he ended up playing for 5 hours.

Set 1:
Walk a Mile in My Shoes (Joe South cover)
One More Cup of Coffee (Valley Below)
Rainy Day Women #12 & 35
Trouble No More (Muddy Waters cover) (live debut)
Been All Around This World (live debut)
Political World (live debut)
Where Teardrops Fall (live debut)
Tears of Rage (The Band cover)
I Dreamed I Saw St. Augustine
It Takes a Lot to Laugh, It Takes a Train to Cry
Everybody's Movin' (Glen Glenn cover)

Set 2:
Watching the River Flow
What Was It You Wanted (live debut)
Oh Babe, It Ain't No Lie (Elizabeth Cotten cover - live debut)
Lenny Bruce
I Believe in You
Man of Peace
Across the Borderline (Ry Cooder cover)
Leopard-Skin Pill-Box Hat
All Along the Watchtower

Set 3:
Tight Connection to My Heart (Has Anybody Seen My Love) (live debut)
Political World
What Good Am I?
Wiggle Wiggle (live debut)
Stuck Inside of Mobile With the Memphis Blues Again
Paid the Price (Moon Martin cover)
Help Me Make It Through the Night (Kris Kristofferson cover)
Man in the Long Black Coat
Congratulations (Traveling Wilburys cover)
Dancing in the Dark (Bruce Springsteen cover - live debut)
(I Heard That) Lonesome Whistle (Hank Williams cover)
Confidential (Sonny Knight cover)
In the Garden
Everything Is Broken

Set 4:
So Long, Good Luck and Goodbye (Weldon Rogers cover)
Where Teardrops Fall
Political World
Peggy-O
I'll Remember You
Key to the Highway (Charles Segar cover - live debut)
Joey
Lay Lady Lay
I Don't Believe You (She Acts Like We Never Have Met)
When Did You Leave Heaven? (Johnny “Guitar” Watson cover)
Maggie's Farm
Been All Around This World
In the Pines
Highway 61 Revisited
Precious Memories (John Wright cover)
Like a Rolling Stone
He did a show immediately after this one at a theater in Princeton that my father and stepmother went to. Both shows were warm-ups for what became The Never Ending Tour. They said his voice was horrible and at times unintelligible.
 
94. “Isis” (1976, from Desire)

https://youtu.be/INilAY6aJTc

Dylan’s magnum opus about marriage from the underrated Desire (I think this album suffers in some ratings because it followed Blood on the Tracks, and so it gets compared to perfection. Also because it’s connected to that dreadful film Renaldo and Clara. However, Rolling Stone magazine regards it as one of Dylan’s best.)

Covers This is one of those rare songs on this this for which there are no significant covers from other artists that I am aware of (if anyone is please let us know.) However Dylan himself has had live versions of “Isis” that are more upbeat than the original, the most famous of these is from his Rolling Thunder Review tour, also in 1976, and first released on one of his bootleg albums. It was actually this live version that first really attracted me to the song; I had sort of ignored it before.

https://youtu.be/Ojyk0g0bijM
Said live version is far superior to the studio version. It’s like they’re not even the same song.
 
92. “Outlaw Blues” (1965, from Bringing It All Back Home”)

I don’t have a good link for this since I’m not willing to pay extra for YouTube’s premium service. This is one of those songs, along with some others coming up a little later on this list, which so angered the folkie crowd that loved Bob on an acoustic guitar and hated rock and roll (there is a terrific book on this subject, Dylan Goes Electric- highly recommended. Dylan turns the amplifier way up here and any resemblance to Pete Seeger or the New Christy Minstrels is long gone.

Covers Outlaw Blues is a straight up hard rocking blues tune so it got covered a lot. My favorite is probably Dave Edmunds with Rockpile:

https://youtu.be/PxSrVa8FCkU
Timothee Chalomet performing this on SNL was not on my bingo card, but I did see it.
 
Every Grain of Sand is one of his best. Probably my favorite of the Christian songs.
It’s one I really debated. I like it far better than “Gotta Serve Somebody” which never impressed me at all. “Every Grain of Sand” and “Shooting Star” were the last two that I cut.

I really like those Christian albums and there are two songs (one from each of the first two) that I regard as masterpieces, and they are included coming up a little later.
Every Grain of Sand is one of Dylan's most compelling songs, regardless of whether you look at it from a Christian lens. It would be a lock for my top 100 Dylan.

Yes, I am hippling this thread. It was created when I wasn't coming to the FFA.
 
I’m surprise I’m saying this because I also prefer his initial peak period but there wasn’t enough later Dylan on the list imo.
 
81. "When I Paint My Masterpiece" (1971, Unreleased)

https://vimeo.com/75113136

The song was written for The Band, though the above is Dylan's own version which was later added to his second greatest hits collection. I always think of this song as a travelogue of Rome; last summer when I stood on the Spanish steps I couldn't help singing it.

Covers: It's been performed lots of times over the years but it would be derelict of me not to present here the guys who were supposed to perform it:

https://www.youtube.com/watch?v=wq2e7DPhyHg
It was actually a response to haters who were asking "when are you going to write good songs again?" New Morning and, especially, Self Portrait were not well received.
 
71. “All I Really Want to Do” (1964, from Another Side of Bob Dylan)

https://youtu.be/UIG3xgIZWZ8

Some of his most famous lyrics here and in his signature style:

Simplify you, classify you, deny, defy, or crucify you

Who else writes like that? You hear that cadence and you know it’s Dylan right away. The chorus employs a Jimmy Rodgers like yodel.

Covers Somewhat surprisingly there aren’t that many covers of this one; the most famous are by The Byrds and Cher. Since we’ve already heard Roger McGuinn and friends and will be encountering them a few more times before All is said and done, I figure I’d go with Cher here who actually does a fine job with a pop style somewhat similar to how Judy Collins handled “Both Sides Now”:

https://youtu.be/URsD357DyAw
This is one of Dylan's worst vocals and I think it was deliberate. His voice is totally out of control and it doesn't have to be.

My sophomore year of college, someone opened their window and was playing Dylan records at a loud volume so the whole courtyard could hear it. When it got to this song, someone from the dorm room next door opened their window and yelled out, "I HATE BOB DYLAAAAAAAAAAAAAAAAAAAAAN!!!!!!"

The Byrds' version is amazing, though.
 
46. “Hurricane” (1975, from Desire)

https://youtu.be/1FOlV1EYxmg

This is a straightforward narrative protest song in the style of “Only a Pawn In Their Game” and “The Lonesome Death of Hattie Carroll”, though written over a decade later at a time when Dylan was thought to have evolved from such efforts. It’s a bit controversial because some of the “facts” are still disputed to this day (the excellent Denzel Washington movie of the same name has only added to the mythology of Rubin Carter- I’m not saying he was guilty of the murder he was charged with, he probably wasn’t though nobody can say for sure- but he certainly wasn’t the heroic figure the song and movie claim, and he NEVER would have been champion of the world.)

That being said this is a great rock and roll song, well deserving of Dylan’s top 50. The only question is why I don’t have it ranked even higher: it’s one of his most famous songs and some critics have it in their top 10. The reason I don’t is because lyrically it lacks the poetic quality of the very best of Dylan’s music; it’s a little too basic, a little too unsubtle. Still a wonderful tune though.

Covers The only cover I’ve been able to find for this song by a (somewhat) noteworthy artist is by Ani DiFranco, and I’m not going to link it because I think it’s awful.
Top 5 for me. I don't get your criticism of the lyrics - obviously it's based on a true story but I think he does a masterful job creating imagery and while maybe it doesn't have the "poetry" it certainly has his biting scathing style that he'll unleash when warranted.
46. “Hurricane” (1975, from Desire)

The reason I don’t is because lyrically it lacks the poetic quality of the very best of Dylan’s music; it’s a little too basic, a little too unsubtle. Still a wonderful tune though.
This is excellent analysis and is why the song wouldn't dent my top 100. Unsubtle.
In a nutshell, this is emblematic of how no two Dylan lists will ever be alike. His material is so diverse and his appeal is so varied that hardcore fans can have impassioned debates over the quality of his songs.
 
43. “Day of the Locusts” (1970, from New Morning)

https://www.megalyrics.net/bob-dylan/day-of-the-locusts#play

Taking its title from a famous Nathaniel West novel about Hollywood, Dylan sings at the top of his lungs about chills, diplomas, and sweet memories while banging away at his piano.

Covers None that I know of by a significant artist.
He wrote this after receiving an honorary degree from Princeton University. He brought David Crosby, of all people, to the ceremony with him. 1970 was one of the years where the 17-year cicadas emerged on the East Coast. They make a ton of noise and were exceptionally loud at the ceremony.
 
28. “Positively 4th Street” (1965, released as a single)

https://youtu.be/aehwEu8SBSo

Probably the second most cutting of all Dylan songs (the clear #1 in this category is coming up later.) Bob is apparently bitter that this person didn’t support him when he abandoned folk for rock and roll (supposedly it’s all the folks in Greenwich Village) and so he lashes out. There’s no subtlety here; it’s a straight up attack.

Musically this song kind of reminds me of Neil Young’s “Harvest” in that there’s no bridge, chorus, or progression; it’s just the same couple of lines over and over. Yet somehow it works.

Covers Lots of faithful renditions of this, lots of unfaithful ones too, and some of these don’t work (the Violent Femmes, for example, a band I used to love, just destroy this song). I really like Lucinda Williams’ version. (Lucinda is an artist I think I would enjoy more except for how she tries to sound drunk all the time- or maybe she is?)

https://youtu.be/ea6R-sALVlA
You're not alone. Lucinda Williams' voice does not bother me as much as Tom Waits' does, but it's closer than I would like. Unfortunately it's even worse now because she had a stroke.

I really like what the Byrds did with this one as well.
 
19. “All Along the Watchtower” (1967, from John Wesley Harding)

https://youtu.be/bT7Hj-ea0VE

Per wiki, this is the song that Dylan has performed most often in his live shows. That surprises me. I’m not sure what I would have guessed if asked but I don’t think it would have been this one.

Its said that the Dylan version is about the lyrics and the Hendrix version is about the music. Lyrically this song could fit right in on any Led Zeppelin album.

Covers Obviously, Jimi:

https://youtu.be/TLV4_xaYynY
Soon after Hendrix' death, Dylan began performing this song Hendrix-style as a tribute to him. For obvious reasons, that version became a consistent highlight of his sets, so it does not surprise me at all that it has the most documented live performances. Keep in mind that setlist recordkeeping in the early years of an artist's career is usually pretty spotty.

He has played this every single time I have seen him, always as one of the last songs.
 
17. “My Back Pages” (1964, from Another Side of Bob Dylan)

https://youtu.be/92cF_KCH7TU

For some reason I know this entire song by heart, word for word, despite the indecipherable lyrics. Well actually I sort of get what he’s talking about. I used to think that the last line of each verse was just a smart play on words, but then it occurred to me that he really is making a point about the relativity of age. My favorite verse, from memory:

A self ordained professor’s tongue too serious to fool

shouted out that liberty is just equality in school

equality, I spoke the word as if a wedding vow

Ah but I was so much older then I’m younger than that now


Covers On the Byrds’ version (from their album Younger Than Yesterday) Roger McGuinn introduced a guitar lead on his 12 string Rickenbacker that came to define the song. Then in 1992 a group of very famous people performed the Byrds’ version (with the same guitar lead) for the Bob Dylan 30th Anniversary Concert, creating the best ever cover of this fine tune. The featured artists are:

Verse 1- Roger McGuinn

Verse 2- Tom Petty

Verse 3- Neil Young

Guitar solo interlude- Eric Clapton

Verse 4- Eric Clapton

Verse 5- Bob Dylan

Verse 6- George Harrison

Enjoy:

https://youtu.be/rGEIMCWob3U
You'd think Bob would take the first verse or the last. Seems typical of him to do the unexpected and take the next-to-last. Maybe it's his favorite verse. More likely, it's him being random.

The Hendrix AATW is the consensus pick of Dylan cover that is better than Dylan original. (I ranked it #1 in Krista's covers countdown.) I would argue that the Byrds' version of My Back Pages outperforms Dylan's original almost to the same degree.
 
8. “Make You Feel My Love” (1997, from Time Out of Mind)

https://youtu.be/fdWto-AUM3Q

It’s simply amazing that, nearly five decades after he started, Bob Dylan could still write a song this lovely, arguably the most beautiful love song of his long career.

The 90s didn’t begin well for Bob Dylan. He appeared on the Grammys and performed a disastrous, terrible version of “Masters of War”, probably the nadir of his life as an artist, worse than Self Portrait, worse than Live at Budokan. He was laughed at, mocked on late night TV. Critics demanded he retire as his voice was gone. Dylan then released two albums of folk and blues standards, sparsely recorded, which a few critics liked but nobody paid much attention to. He was no longer relevant, he appeared to be done.

And then...Time Out of Mind. Talk about redemption! Out of nowhere comes this album of new, great songs. It won the Grammys’ album of the year. And other artists began to record “Make You Feel My Love” beginning with Billy Joel, which started to make it known to the public even if most people weren’t aware of who wrote it. Then in the 2000s, it took off thanks to...

Covers ...Adele. She made the song famous, and made it her own. Millions of her fans, including my daughters, simply assumed that she wrote it. And indeed she does make it her own with that amazing voice- it’s one of the best recordings IMO of the 21st century.

https://youtu.be/0put0_a--Ng
My first spin through TOOM, I got to this song and said "this would be a massive hit if recorded by someone with a 'better voice'".

And it was. First in the country world for Garth Brooks, then in the pop world for Adele.
 
2. “Tangled Up in Blue” (1975, from Blood On the Tracks)

https://youtu.be/YwSZvHqf9qM

1. “Like a Rolling Stone” (1965, from Highway 61 Revisited)

https://youtu.be/IwOfCgkyEj0

Time to wrap this up. The top 2 songs are pretty anticlimactic. Two of the greatest songs ever written and I don’t have much further to add to that. I also don’t have covers to present (even though there’s one I really like by the Indigo Girls of Tangled Up in Blue; the original songs are too good to consider them.)
I did a Dylan song draft on another board. Had the first overall pick and took Like a Rolling Stone because, as divergent as Dylan's stuff gets, there really is no other choice for this distinction. Its musical and cultural impact was monumental and it has lost none of its luster all these years later.

I got It's Alright Ma, I'm Only Bleeding and Idiot Wind at the 2-3 turn, so I think I "won".
 
I’m surprise I’m saying this because I also prefer his initial peak period but there wasn’t enough later Dylan on the list imo.
I would strongly consider these songs from 1997 and later that weren't on Tim's list:

Love Sick
Cold Irons Bound
Highlands
Things Have Changed
High Water (for Charley Patton)
Honest With Me
Thunder on the Mountain
Ain't Talkin'
Beyond Here Lies Nothin'
Pay in Blood
Tempest
 
Thank you guys for revisiting this thread! It was really a lot of fun at the time,

In the years since I’ve done it the biggest change for me is I would have “Every Grain of Sand” in my top 50. I’ve come to love that tune.
 

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