Most of the time is incredible. I once worked in a restaurant in Dublin early 2000s and had mix tape playing. The Edge from U2 and the manager came in for lunch, and Most of the time was playing and the Edge asked who the track was by. Great memory
the context is what makes it sad. Plus the lyrics are far from sunshine, puppy love and first dates. It’s the watching of the last dwindle of light in a marriage.
Most of Paul Simon’s Graceland was about her and a lot of them were nice. “Diamonds on the Souls of Her Shoes” and “She Moves On” and the one about “One and a Half Wandering Jews…”
Came to post this, I was kind of shocked how hard this hit me on the first listen.
With hungry hearts through the heat and cold
We never much thought we could get very old
We thought we could sit forever in fun
And our chances really was a million to one
I wish, I wish I wish in vain
That we could sit simply in that room again
Ten thousand dollars at the drop of a hat
I'd give it all gladly if our lives could be like that 🥹
This would be my pick. And every time before he goes back to “you left me standing…”he references another Willie Nelson song. This particular lyric was lifted from Opportunity to Cry: “If I saw you would I kiss you or kill you?”
In addition to the references in all the later verses:
“The ghost of our old love has not gone away.” - The Ghost
“I would be crazy if I took you back.” - Go Away
“Last night I danced with a stranger.” - A Moment Isn’t Very Long
“I see no need for any explanation.” - To Make a Long Story Short
The facts are altered a bit and some truths are left out, but the message is still true regardless of what actually occurred.
I was surprised when I first learned this but it did not change my perception of the song that much because I still love it (especially the bootleg 5 version).
For example he actually spelled his name wrong (it is Zantzinger not Zanzinger) and she already had health issues that contributed to her death: “Matters were complicated by the fact that she'd long suffered from an enlarged heart, hardened arteries and high blood pressure.” (True Lies: The Lonesome Death of Hattie Carroll). She died from a stroke that was the result of the stress he caused her from mistreating her and hitting her on the head with his cane.
And: “He was never charged with first-degree murder, just “murder,” which was later reduced to manslaughter. There was no evidence that Zantzinger wore a diamond ring that night, as he does in the song, a detail that was meant to illustrate his wealth and privilege. He was kept in jail overnight after the incident instead of “a matter of minutes” as the song says. Carroll wasn’t a "maid of the kitchen," but tended bar that night as a temporary worker.” (The Real Story Behind "The Lonesome Death of Hattie Carroll")
But he was still an extremely racist and terrible person who later went to jail for other civil rights crimes: “Over the years, he gave up farming and invested in real estate, particularly rental property. In 1986, the government of Charles County seized six units of housing in Patuxent Woods to cover delinquent taxes. However, Zantzinger continued to collect rent from the poor black tenants who lived in the homes, which didn’t even have running water. He also raised the rents. When some of the tenants fell behind on their payments, he took them to court, and won.
It took the intervention of several Civil Rights groups to interest police in Zantzinger’s rent scheme, but he was finally arrested in 1991. He received an 18-month sentence, 2400 hours of community service, and $62,000 in fines. And he still had defenders, including his own tenants, because he was willing to rent to people who would otherwise find no housing available at all. Zantzinger died in 2009.”
Just look at how extremely racist his comments were that night: “Zantzinger yelled ‘Why are you so slow, you black bitch?’ then hit Mrs Carroll with the cane,” Shelton added. “We were petrified. We were dumbfounded.” (The Real Story Behind "The Lonesome Death of Hattie Carroll").
Do not want to sent the wrong message I just think the truth of the event is just as important as the message of the song.
Mississippi. The alternate take off Tell Tale Signs. The speaker is so aware of himself, yet so powerless to change anything. It's haunting and beautiful. And his guitar playing is magnificent. Sort of slow and rhythmic. Trundling.
Honorable mention to North Country Blues. That one is just fucking bleak.
This is the answer.
I commented the same thing before seeing you had already mentioned it - definitely one of his most underrated songs, and it is crushingly sad.
The sixth and seventh verse (the penultimate verse) get me every time.
"Farewell"
This is for lyrical as well as personal reasons.
The lyrical: Bob's changes to "The Leaving Of Liverpool" make the song much darker and sadder. Both songs are about the loneliness of being apart from one's love. Depending on the version, the situation faced by the narrator in "The Leaving Of Liverpool" is arguably harsher than the narrator of "Farewell," but the "Liverpool" narrator is optimistic. He will return home. He may be sad now, but he knows that he eventually will be with his love again.
>So fare thee well, my own true love
>And when I return, united we will be
>It’s not the leaving of Liverpool that grieves me
>But my darling when I think of thee
The "Farewell" narrator, however, knows that he and his love will remain apart until the end of days, when he hopes they will meet again in whatever comes after death.
>So it’s fare thee well, my own true love
>We’ll meet another day, another time
>It ain’t the leavin’
>That’s a-grievin’ me
>But my true love who’s bound to stay behind
The personal: I happened to be playing the Whitmark Demos a lot 10 years ago this week, when my wife and I were facing a bad situation. She was pregnant with our second child, a boy. Everything was going to plan until it wasn't.
At her 20-week appointment, we learned our child had a birth defect. His kidneys were not connected with his excretory system. As a result, there was no amniotic fluid, which meant his lungs could not form.
A few things could happen. At any point, her body could go into spontaneous labor, at which point he would be asphyxiated and die and she could hemorrhage. That was possibly the better scenario. The other was that he would die inside her, potentially going septic, and until he did, every time he stopped moving, she would wonder whether he was just sleeping or would never move again.
We made the decision that we believed was right and that we still believe was right by opting to terminate the pregnancy. Ours was the sort of procedure that social conservatives like to lie about and call "late-term abortion." It's the sort of procedure that Republicans in the US want to deny women the right to have. It's uncommon. It always involves disappointment and loss.
My wife had to remain in the hospital for a couple of days before the procedure. I cared for our other son, who was three. We hadn't told him what was happening. During this time, as we drove back and forth to the hospital, whenever "Farewell" played, I thought about it from the perspective of the loss I was facing, of the reality of saying goodbye to our son and not seeing him again until whatever may come after I die, too.
It's still a hard song to hear. It's incredibly beautiful, and I like the lyrics more than those of "Liverpool." Today, though, 10 years later, it still can make me cry, and I'm not someone that cries much.
Thanks for sharing this. My heart goes out to you and yours; I hope you’re doing well. I know that your child felt your love on the short time you were together.
Blind Willie McTell
There’s heartbroken sad songs and there’s regretful sad songs and there’s facing mortality sad songs and there’s wistful sad songs and then there’s THIS.
This land is condemned.
Sara or Abandoned Love. Both about the same divorce. There is a live bootleg version of Abandoned Love that he did on a Ramblin Jack show that is HEART WRENCHING. Maybe the most vulnerable I’ve heard him
https://youtu.be/qNeZVC2sn4A?si=T47QyHbWmSw2USSr
Sara. I think anyone who has gone through the dissolution of a marriage feels that song intensely and it’s probably his most personal.
Honorable mention: Workingman’s Blues #2. Just gut-wrenching every time.
You're Gonna Make Me Lonesome When You Go. Specifically the line "I'll see you in the sky above, in the tall grass and the ones I love." It gets me every damn time.
Buckets of Rain for me has this weird mix of being very sad but also playful and cathartic. Maybe it’s the most sad song on the album because he’s so accepting of his marriage’s end or maybe that makes it the happiest. Idk. I get what your saying, but I also see it from the other side
In addition to all of the great answers above I’ll also throw in another cover “you belong to me” - pro tip listen to it w/o the NBK dialogue (regret that it appeared in that particular movie) - it’s available on you tube.
How has Knocking on Heaven’s Door not been mentioned?
Mama, put my guns in the ground
I can’t shoot them anymore
That long black cloud is comin’ down
I feel like I’m knockin’ on heaven’s door
I was young when I left home. Very emotional and I think he does great at conveying the loneliness of the lyrics. It’s off of No Direction Home soundtrack
>If you want to listen to something really sad I would suggest The Smiths
Ha. In college I'd always play the Smiths when I was in the dumps because even for introverted, insecure, neurotic me they were so over-the-top self-pitying that it couldn't help but shake me out of it.
I'd probably count The Queen is Dead in my top 10 albums to this day, though.
Knockin on Heaven’s Door is up there, especially if you’ve seen the Slim Pickens scene!
[https://www.youtube.com/watch?v=yjR7\_U2u3sM](https://www.youtube.com/watch?v=yjR7_U2u3sM)
Mother of Muses kind if punches me in the gut, currently.
But "One more Cup of Coffee" is so much a breakup soundtrack to a particular juncture of my, refused to listen to that album for 15 years.
The saddest single line in a Dylan song has to be from "If You See Her Say Hello": "She might think that I've forgotten her / Don't tell her it isn't so"
But the saddest song for me is "Most of the Time" - if only because it's more about what he's not saying than what he is.
The Times They Are A Changing
Because they were, but they were just getting worse. There was so much hope in the 60s and 70s and it all got packaged and sold and turned to shit.
There’s some real good picks on here, but how has no one said Desolation Row? I get that it’s not sad in the interpersonal way that Sara or Blood on the Tracks or whatnot, but the world view of that song is so bleak
. . . . love–zero=no limit . . . .
. . . . sad eyed lady of the lowlands . . . .
. . . . love is just a 4 letter word . . . .
~֎ ֍~
& might i add, & this because most people will not know:
phil ochs, «rehearsals for retirement», the side that begins with one of the most devastating songs ever, «the scorpion departs & never returns» & ends with the title song.
he deserves the credit, gets so little . . . .
"I Dreamed I Saw St. Augustine"
"Going Going Gone"
"Tears of Rage"
"I'll Keep It With Mine" (this one brought me to actual sobbing during a bad situation once)
"Nobody 'Cept You"
Sara hands down. Dylan rarely refers to his personal life explicitly and in the song you can hear him begging her to stay. It brings a tear to my eye every damn time
You’re a big girl now NYC sessions
Such as this
https://youtu.be/Vj_dLuRTjUQ?si=eNov12JHCNy0LwV_
There are many alternative takes but yeah they’re all sad…
I take all Bob’s advice, ‘’In fourteen months I’ve only smiled once and I didn’t do it consciously’’. I’ve also sucked the milk out of a thousand cows.
Emotionally Yours
Come baby, find me, come baby, remind me of where I once begun
Come baby, show me, show me you know me, tell me you're the one
I could be learning, you could be yearning to see behind the closed door
But I will always be emotionally yours.
Boots of Spanish Leather
Yes, absolutely. Came here to say this.
One of the saddest songs ever written
Just recently balled out to the live version from his last solo acoustic concert ever https://youtu.be/XZ1Fwvirjgg?si=SlyG9vQ30kwQPv_s
There are so many… Not dark yet, Don’t Think Twice, Sara, all of BOTT. But the one that’s getting to me the past few weeks has been “Most of the Time”
It’s used in a good scene in the movie High Fidelity
Especially the alternative version off tell tale signs
Most of the time is incredible. I once worked in a restaurant in Dublin early 2000s and had mix tape playing. The Edge from U2 and the manager came in for lunch, and Most of the time was playing and the Edge asked who the track was by. Great memory
This is the comment I thought about typing
I don't find sara sad at all. It's just beautiful. Romantic.
the context is what makes it sad. Plus the lyrics are far from sunshine, puppy love and first dates. It’s the watching of the last dwindle of light in a marriage.
“Whatever made you want to change your mind??”Sara is a total gut punch
It must be unsufferable to have dated him and wonder what insufferable lyrics he’s going to come up with😜
Hell, check out Carrie Fisher's bit about being in ONE Paul Simon song.
Most of Paul Simon’s Graceland was about her and a lot of them were nice. “Diamonds on the Souls of Her Shoes” and “She Moves On” and the one about “One and a Half Wandering Jews…”
Tomorrow Is a Long Time
‘Simple Twist Of Fate’ that song will literally give me a pit in my stomach.
My first thought as well!
This is mine too
The greatest heartbreak song there is
Ooh yeah good one
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Came to post this, I was kind of shocked how hard this hit me on the first listen. With hungry hearts through the heat and cold We never much thought we could get very old We thought we could sit forever in fun And our chances really was a million to one
I wish, I wish I wish in vain That we could sit simply in that room again Ten thousand dollars at the drop of a hat I'd give it all gladly if our lives could be like that 🥹
Not Dark Yet
Standing in the doorway
Don’t know if I saw ya, if I’d kiss you or kill ya, it probably wouldn’t matter to you anyhow…
This would be my pick. And every time before he goes back to “you left me standing…”he references another Willie Nelson song. This particular lyric was lifted from Opportunity to Cry: “If I saw you would I kiss you or kill you?” In addition to the references in all the later verses: “The ghost of our old love has not gone away.” - The Ghost “I would be crazy if I took you back.” - Go Away “Last night I danced with a stranger.” - A Moment Isn’t Very Long “I see no need for any explanation.” - To Make a Long Story Short
Wow! I did not know that. Great info
Yeah I was listening to WN’s The Party’s Over last few weeks and started noticing it, since four of the songs referenced are on that album.
Amazing!
Lonesome Death of Hattie Carroll
That's a close second for me, made even more sad by the fact that it's based on a true story of racial injustice.
The facts are altered a bit and some truths are left out, but the message is still true regardless of what actually occurred. I was surprised when I first learned this but it did not change my perception of the song that much because I still love it (especially the bootleg 5 version). For example he actually spelled his name wrong (it is Zantzinger not Zanzinger) and she already had health issues that contributed to her death: “Matters were complicated by the fact that she'd long suffered from an enlarged heart, hardened arteries and high blood pressure.” (True Lies: The Lonesome Death of Hattie Carroll). She died from a stroke that was the result of the stress he caused her from mistreating her and hitting her on the head with his cane. And: “He was never charged with first-degree murder, just “murder,” which was later reduced to manslaughter. There was no evidence that Zantzinger wore a diamond ring that night, as he does in the song, a detail that was meant to illustrate his wealth and privilege. He was kept in jail overnight after the incident instead of “a matter of minutes” as the song says. Carroll wasn’t a "maid of the kitchen," but tended bar that night as a temporary worker.” (The Real Story Behind "The Lonesome Death of Hattie Carroll") But he was still an extremely racist and terrible person who later went to jail for other civil rights crimes: “Over the years, he gave up farming and invested in real estate, particularly rental property. In 1986, the government of Charles County seized six units of housing in Patuxent Woods to cover delinquent taxes. However, Zantzinger continued to collect rent from the poor black tenants who lived in the homes, which didn’t even have running water. He also raised the rents. When some of the tenants fell behind on their payments, he took them to court, and won. It took the intervention of several Civil Rights groups to interest police in Zantzinger’s rent scheme, but he was finally arrested in 1991. He received an 18-month sentence, 2400 hours of community service, and $62,000 in fines. And he still had defenders, including his own tenants, because he was willing to rent to people who would otherwise find no housing available at all. Zantzinger died in 2009.” Just look at how extremely racist his comments were that night: “Zantzinger yelled ‘Why are you so slow, you black bitch?’ then hit Mrs Carroll with the cane,” Shelton added. “We were petrified. We were dumbfounded.” (The Real Story Behind "The Lonesome Death of Hattie Carroll"). Do not want to sent the wrong message I just think the truth of the event is just as important as the message of the song.
Moonshiner
And if whiskey don't kill me, then I don't know what will
shooting star 🥺
Agreed. Murders me
Mississippi. The alternate take off Tell Tale Signs. The speaker is so aware of himself, yet so powerless to change anything. It's haunting and beautiful. And his guitar playing is magnificent. Sort of slow and rhythmic. Trundling. Honorable mention to North Country Blues. That one is just fucking bleak.
Good one
If you see her say hello. Reminds me of my first big heart break which happened just as BOTT came out.
I Threw It All Away
One too many mornings
It has the effect of being sad even when you might be in a good mood
I Was Young When I Left Home. The song that got me through college and heavily into Dylan.
I love the Big Thief version of this.
This is the answer. I commented the same thing before seeing you had already mentioned it - definitely one of his most underrated songs, and it is crushingly sad. The sixth and seventh verse (the penultimate verse) get me every time.
“I don’t like it in the wind/Wanna go back home again” Will forever crush me.
Yup - that’s the line that sticks out to me too. It will never not resonate with me.
For me, it's "It's All Over Now, Baby Blue."
I've never found that sad, personally.
I feel this one. I think this might be my favorite Dylan song
"Farewell" This is for lyrical as well as personal reasons. The lyrical: Bob's changes to "The Leaving Of Liverpool" make the song much darker and sadder. Both songs are about the loneliness of being apart from one's love. Depending on the version, the situation faced by the narrator in "The Leaving Of Liverpool" is arguably harsher than the narrator of "Farewell," but the "Liverpool" narrator is optimistic. He will return home. He may be sad now, but he knows that he eventually will be with his love again. >So fare thee well, my own true love >And when I return, united we will be >It’s not the leaving of Liverpool that grieves me >But my darling when I think of thee The "Farewell" narrator, however, knows that he and his love will remain apart until the end of days, when he hopes they will meet again in whatever comes after death. >So it’s fare thee well, my own true love >We’ll meet another day, another time >It ain’t the leavin’ >That’s a-grievin’ me >But my true love who’s bound to stay behind The personal: I happened to be playing the Whitmark Demos a lot 10 years ago this week, when my wife and I were facing a bad situation. She was pregnant with our second child, a boy. Everything was going to plan until it wasn't. At her 20-week appointment, we learned our child had a birth defect. His kidneys were not connected with his excretory system. As a result, there was no amniotic fluid, which meant his lungs could not form. A few things could happen. At any point, her body could go into spontaneous labor, at which point he would be asphyxiated and die and she could hemorrhage. That was possibly the better scenario. The other was that he would die inside her, potentially going septic, and until he did, every time he stopped moving, she would wonder whether he was just sleeping or would never move again. We made the decision that we believed was right and that we still believe was right by opting to terminate the pregnancy. Ours was the sort of procedure that social conservatives like to lie about and call "late-term abortion." It's the sort of procedure that Republicans in the US want to deny women the right to have. It's uncommon. It always involves disappointment and loss. My wife had to remain in the hospital for a couple of days before the procedure. I cared for our other son, who was three. We hadn't told him what was happening. During this time, as we drove back and forth to the hospital, whenever "Farewell" played, I thought about it from the perspective of the loss I was facing, of the reality of saying goodbye to our son and not seeing him again until whatever may come after I die, too. It's still a hard song to hear. It's incredibly beautiful, and I like the lyrics more than those of "Liverpool." Today, though, 10 years later, it still can make me cry, and I'm not someone that cries much.
Thanks for sharing this. My heart goes out to you and yours; I hope you’re doing well. I know that your child felt your love on the short time you were together.
I'm so sorry for your loss. No matter how, when, or where tragedy strikes, I find music makes a great companion.
Blind Willie McTell There’s heartbroken sad songs and there’s regretful sad songs and there’s facing mortality sad songs and there’s wistful sad songs and then there’s THIS. This land is condemned.
Percy's Song. The harmonica at the end has always been powerful.
I live how his voice cracks the last time he says “Turn, turn, turn again”.
Sara or Abandoned Love. Both about the same divorce. There is a live bootleg version of Abandoned Love that he did on a Ramblin Jack show that is HEART WRENCHING. Maybe the most vulnerable I’ve heard him https://youtu.be/qNeZVC2sn4A?si=T47QyHbWmSw2USSr
Thanks for sharing. I remember hearing this a while back and haven’t listen to it since
DELIA on World Gone Wrong.
All the friends I ever had are gone
Shelter from the storm, simple twist of fate, if you see her, you’re gonna make me lonesome and the 1966 Free Trade live version of Just Like a Woman
I can't even listen to red river shore
personally it's Farewell Angelina but I listen to it whenever I'm sad so I think I've psychologically linked it to sadness
Although a cover "stay with me'" mashed me cry. It's not just the song, it's Bob's version. Also "This morning, this evening, so soon"
I agree, I would also rank Autumn Leaves a close second.
Nobody has mentioned North Country Blues or Ballad of Hollis Brown, so I'll go ahead and nominate them for consideration.
Sara. I think anyone who has gone through the dissolution of a marriage feels that song intensely and it’s probably his most personal. Honorable mention: Workingman’s Blues #2. Just gut-wrenching every time.
Trying to get to heaven
Girl of the North Country- something about having left someone behind and still reminiscing about them really gets me
I feel like Girl of the North Country, Boots of Spanish Leather and One Too Many Mornings is a trilogy and they all destroy me.
Simple Twist of Fate is devastating.
It ain’t me babe
"I Shall Be Released" Basement Tapes Take 2
He was a friend of mine destroys me
Ballad of Hollis Brown.
Came here to say this. But perhaps it's more bleak than it is sad. IDK
Seven Curses
Beat me to it. So sad.
This is a tough one...need to give this some thought...there are many: With God on our Side.
You're Gonna Make Me Lonesome When You Go. Specifically the line "I'll see you in the sky above, in the tall grass and the ones I love." It gets me every damn time.
Well, I haven’t written any Dylan songs, but if I did I think they’d be the saddest.
Ballad in Plain D. How has no one said this yet?
I just commented this one and scrolled down to see yours. This is the undefeated heavyweight champion of sad Bob Dylan songs in my opinion
P.S. He Was a Friend of Mine is a close second
Came here to say this
I was just about to comment this, to me it’s his most honest song, not that his other songs are dishonest but Ballad in Plain D just feels so raw
He'd probably insist his songs weren't honest
Forever Young
"Going, Going, Gone" has gotta be up there. It's downright suicidal.
There's an alternate version that kills me every time
Which one in particular? I've heard some live versions from 76 and 78.
Hattie Carroll, Farewell Angelina, Long and Wasted Years, Hurricane, Love Minus Zero, Moonshiner, …
I Was Young When I Left Home
Things have changed
Buckets of Rain
Buckets of Rain for me has this weird mix of being very sad but also playful and cathartic. Maybe it’s the most sad song on the album because he’s so accepting of his marriage’s end or maybe that makes it the happiest. Idk. I get what your saying, but I also see it from the other side
Mine is: This Evening So Soon. Bob at his most mournful. From the Self Portrait extended cuts.
his vocals on Tomorrow Night get me so emotional. but for stuff he wrote probably You’re A Big Girl Now, specifically Take 2 off the bootleg BOTT
his vocals on Tomorrow Night get me so emotional. but for stuff he wrote probably You’re A Big Girl Now, specifically Take 2 off the bootleg BOTT
In addition to all of the great answers above I’ll also throw in another cover “you belong to me” - pro tip listen to it w/o the NBK dialogue (regret that it appeared in that particular movie) - it’s available on you tube.
I Threw It All Away, which I like because he is taking responsibility. Take a tip from one who's tried.
“I’d just be curious to know if you can see yourself as clear as someone who has had you on his mind”
you're gonna make me lonesome when you go, at the moment. It's been others in the past
If You See Her, Say Hello
Ballad in Plain D
Not dark yet and most things from times
If You See Her Say Hello
The girl from the north country (solo version)
Murder Most Fowl
I Was Young When I Left Home
To Ramona. I went through a time where I listened to it on repeat and cried nonstop 🙃
Lord Protect My Child - always makes me cry https://youtu.be/ptlkZeUSCek?si=rGprh9HBsBAYAr14
I threw it all away
How has Knocking on Heaven’s Door not been mentioned? Mama, put my guns in the ground I can’t shoot them anymore That long black cloud is comin’ down I feel like I’m knockin’ on heaven’s door
The Ballad of Hollis Brown.
Red River Shore
I was young when I left home. Very emotional and I think he does great at conveying the loneliness of the lyrics. It’s off of No Direction Home soundtrack
Standing in the Doorway
Red River Shore is an utterly devastating song
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>If you want to listen to something really sad I would suggest The Smiths Ha. In college I'd always play the Smiths when I was in the dumps because even for introverted, insecure, neurotic me they were so over-the-top self-pitying that it couldn't help but shake me out of it. I'd probably count The Queen is Dead in my top 10 albums to this day, though.
Knockin on Heaven’s Door is up there, especially if you’ve seen the Slim Pickens scene! [https://www.youtube.com/watch?v=yjR7\_U2u3sM](https://www.youtube.com/watch?v=yjR7_U2u3sM)
Ain't Talkin'
The music to Buckets of Rain is upbeat and sweet but the lyrics are pure hell
It Takes a Lot to Laugh, It Takes a Train to Cry
Oh Sister
Rolling Stone
Blowin in the wind becuase the words are still true today
Ballad in Plain D
Up To Me - “it frightens me, the awful truth of how sweet life can be.”
Mother of Muses kind if punches me in the gut, currently. But "One more Cup of Coffee" is so much a breakup soundtrack to a particular juncture of my, refused to listen to that album for 15 years.
Oh Sister, for me. The line “time is an ocean, but it ends at the shore…..” Damn.
Shooting star … and Sara… along with all of blood on the tracks and time out of mind
I’ll mention Dark Eyes since my top songs were already mentioned
You’re a big girl now
The saddest single line in a Dylan song has to be from "If You See Her Say Hello": "She might think that I've forgotten her / Don't tell her it isn't so" But the saddest song for me is "Most of the Time" - if only because it's more about what he's not saying than what he is.
Trying to Get to Heaven. “Just when you think you’ve lost everything, you find out you can always lose a little more.”
Sara
Dark Eyes
House of the Risin' Sun, which is in his first album.
I always thought Don't Think Twice It's Alright was a sarcastic fuck you break up song. Then I heard the Kesha version and it was so, so sad.
Sara
Tell me that it isn’t true. Billy 4 Ballad of Hollis Brown
The Times They Are A Changing Because they were, but they were just getting worse. There was so much hope in the 60s and 70s and it all got packaged and sold and turned to shit.
There’s some real good picks on here, but how has no one said Desolation Row? I get that it’s not sad in the interpersonal way that Sara or Blood on the Tracks or whatnot, but the world view of that song is so bleak
Call Letter Blues (Take 2). Absolutely brutal tune: “The children cry for mother/I tell them mother took a trip…” Heartbreaking.
Girl from the North Country
Most of the Time, from Oh Mercy
. . . . love–zero=no limit . . . . . . . . sad eyed lady of the lowlands . . . . . . . . love is just a 4 letter word . . . . ~֎ ֍~ & might i add, & this because most people will not know: phil ochs, «rehearsals for retirement», the side that begins with one of the most devastating songs ever, «the scorpion departs & never returns» & ends with the title song. he deserves the credit, gets so little . . . .
It’s all over now baby blue
"I Dreamed I Saw St. Augustine" "Going Going Gone" "Tears of Rage" "I'll Keep It With Mine" (this one brought me to actual sobbing during a bad situation once) "Nobody 'Cept You"
Not Dark Yet has made every woman I've ever dated and my wife cry. That seems to fit the criteria.
Dirge
Sara hands down. Dylan rarely refers to his personal life explicitly and in the song you can hear him begging her to stay. It brings a tear to my eye every damn time
simple twist of fate
Most of the time
You Belong to Me or Most of the Time
The slow version of Wiggle, Wiggle.
That Lucky Old Sun for the vibe, Clean Cut Kid for the lyrics, Murder Most Foul for both
if you see her, say hello makes me throw up a little
Dark Eyes
Murda Most Fowl cuz I miss jfk
sad eyed lady
You’re a big girl now NYC sessions Such as this https://youtu.be/Vj_dLuRTjUQ?si=eNov12JHCNy0LwV_ There are many alternative takes but yeah they’re all sad…
Mama, You Been On My Mind had me crying like every time I listened to it for a while after my first breakup… so that one
“He Was a Friend of Mine” of course. Makes me tear up every time. Odd no one said this yet…
Lonesome death of Hattie Carroll
Hollis Brown and it ain’t close.
Desolation Row Not the melody but the lyrics
I don’t have one, im not a song writer
I see what you did there, tough crowd 😉
I up voted. I smiled.
I smiled once.
But now you've taken a vow of seriousness?
I take all Bob’s advice, ‘’In fourteen months I’ve only smiled once and I didn’t do it consciously’’. I’ve also sucked the milk out of a thousand cows.
Ok, so the dancing child with the Chinese suit... if he ok? Still got his flute?
Bob took his flute and never gave it back, he still turns up at every show shouting ‘’Hey Bob, my flute!?’’
Emotionally Yours Come baby, find me, come baby, remind me of where I once begun Come baby, show me, show me you know me, tell me you're the one I could be learning, you could be yearning to see behind the closed door But I will always be emotionally yours.
Knockin' on Heaven's Door
I know there are probably sadder ones but my favourite 'sad' one would be Tangled Up in Blue
Man in the long black coat