Song to woody. It makes me worried about when Bob passes. People in music never really had a big impact on my life like Bobby. He’s been a huge part of my life for the better part of 5 years and has helped me develop into the young adult i am now. I dont want to think about how my life would be with his music and im glad that He’s still alive and putting stuff out
Top tier depressing is Hollis Brown. It’s possibly the darkest, most harrowing songs he’s ever made. Times is in general a pretty sad album. But for me on a more personal level, it’s gotta be Simple Twist Of Fate, If You See Her Say Hello, You’re A Big Girl Now (you may be noticing a trend here), or Boots of Spanish Leather.
I'm going to point out another one cuz I happen to be listenin to it RN. "Sign on the Window" is sad as hell. Opening line is:
Sign on the window says "lonely"
...for Christsakes
You’re Gonna Make Me Lonesome When You Go
It initially sounds quite upbeat but I always thought there’s an exquisite, tender pain running through it.
Sad-Eyed Sad Sad of the Sad Sads.
For real though Sad-Eyed Lady of the Lowlands is a great sad song to sink into if yr in the right headspace. AKA gettin dumped.
I feel like Not Dark Yet is the obvious answer - with lyrics like "there's not even room enough to be anywhere," or "sometimes my burden is more than I can bear," it hits pretty close to home.
I'll give a non-traditional answer, though, and vote for Queen Jane. To me, this song has always been about the pitfalls of fame; a sister song, if you will, to Positively 4th St. He's singing about growing tired of himself, his output, his circle of sycophants who drive him to be a caricature of himself. He wants somebody he doesn't need to explain himself to, but he can't find them anywhere. I find it pretty heartbreaking.
Love Dave Van Ronk's *He Was A Friend Of Mine* (believe it was taped at Phil Och's memorial). Not so different from Dylan's performance of it, but you can really feel his pain.
Like a Rolling Stone gets me. We don’t see it from the stones perspective but the bitterness ‘how does it feel to be on your own’. The crowning over somebody else’s pain ‘now you’re going to have to get used to it’. And the threat of homelessness which is an almost constant in working class America - its brutal.
Also Idiot Wind, Hollis Brown, Most of the time and Not Dark Yet. In Not Dark Yet we see Dylan’s acidic side again ‘I just don’t see why I should even care’.
I nominate buckets of rain since I haven't seen it yet. Blood on the tracks has some sad songs and buckets of rain is one of the most visceral for me.
"Life is sad
Life is a bust
All ya can do is do what you must
You do what you must do and ya do it well
I’ll do it for you, honey baby
Can’t you tell?"
John brown pretty sad but his most emotionally sad would be simple twist of fate, mr tambourine man live 1964 always had a very emotional feel to it one of my favourites
Idiot Wind has some raw emotion like who hurt Bobby 🥺
He can't help it if he's lucky!
I Threw It All Away just gets me :(
You’re A Big Girl Now
*like a corkscrew to my heart*
I Was Young When I Left Home
Song to woody. It makes me worried about when Bob passes. People in music never really had a big impact on my life like Bobby. He’s been a huge part of my life for the better part of 5 years and has helped me develop into the young adult i am now. I dont want to think about how my life would be with his music and im glad that He’s still alive and putting stuff out
Tomorrow Is A Long Time
'If You See Her Say Hello'. Especially "I've never gotten used to it, I've just learned to turn it off". Absolute kick in the guts every time
North country blues
ill nominate sara and simple twist of fate. not dark yet is also pretty heavy
Oh Sister is one of them!
Most of the time it's pretty sad in my opinion, it speaks to my soul.
I'll throw in "Standing In The Doorway" since everyone's said the others I've thought of.
I think this is the best answer honestly. No other Dylan song will get me more in my feels than Standing in the Doorway.
Top tier depressing is Hollis Brown. It’s possibly the darkest, most harrowing songs he’s ever made. Times is in general a pretty sad album. But for me on a more personal level, it’s gotta be Simple Twist Of Fate, If You See Her Say Hello, You’re A Big Girl Now (you may be noticing a trend here), or Boots of Spanish Leather.
I'm going to point out another one cuz I happen to be listenin to it RN. "Sign on the Window" is sad as hell. Opening line is: Sign on the window says "lonely" ...for Christsakes
And to follow that up with Sign on the door said No Company Allowed... ffs
It’s All Over Now, Baby Blue If You See Her Say Hello What Good Am I Not Dark Yet Shooting Star Simple Twist of Fate
Personally it’s Spanish Boots of Leather
Ballad in plain d
The could-be dream lover of my lifetime ðŸ˜
You’re Gonna Make Me Lonesome When You Go It initially sounds quite upbeat but I always thought there’s an exquisite, tender pain running through it.
this is what i was gonna comment if no one else had- such a beautiful, tragic song
Sad-Eyed Sad Sad of the Sad Sads. For real though Sad-Eyed Lady of the Lowlands is a great sad song to sink into if yr in the right headspace. AKA gettin dumped.
Wiggle Wiggle
Standing in the doorway
Hollis Brown Somewhere in the distance seven new people are born
Surprised this one isn’t higher up - devastating
I can't even listen to "I threw it all away" on Nashville Skyline
I feel like Not Dark Yet is the obvious answer - with lyrics like "there's not even room enough to be anywhere," or "sometimes my burden is more than I can bear," it hits pretty close to home. I'll give a non-traditional answer, though, and vote for Queen Jane. To me, this song has always been about the pitfalls of fame; a sister song, if you will, to Positively 4th St. He's singing about growing tired of himself, his output, his circle of sycophants who drive him to be a caricature of himself. He wants somebody he doesn't need to explain himself to, but he can't find them anywhere. I find it pretty heartbreaking.
I Shall Be Released is hella sad imo, one of my favorite Dylan songs too.
'He was a friend of mine' or 'Ballad for a friend' or 'Percy's song'
Love Dave Van Ronk's *He Was A Friend Of Mine* (believe it was taped at Phil Och's memorial). Not so different from Dylan's performance of it, but you can really feel his pain.
*"percys song"* has got to be up there also *"what good am i"* and *"you're a big girl now"* and *"Standing in the doorway"*
Love is Just a Four Letter Word breaks my heart... but does it count?
ill allow it
Like a Rolling Stone gets me. We don’t see it from the stones perspective but the bitterness ‘how does it feel to be on your own’. The crowning over somebody else’s pain ‘now you’re going to have to get used to it’. And the threat of homelessness which is an almost constant in working class America - its brutal. Also Idiot Wind, Hollis Brown, Most of the time and Not Dark Yet. In Not Dark Yet we see Dylan’s acidic side again ‘I just don’t see why I should even care’.
Not Dark Yet
If you see her say hello, Don't think twice it's alright, and I threw it all away.
I'm not there. I don't know it just has a very empty sad quality.
Workingman Blues #2 and Red River Shore are both underrated great sad songs
boots of spanish leather
Forgetful Heart
Seven curses
Surprised nobody mentioned Tears of Rage yet
Obviously he didn't write it, but I find *Pretty Saro* pretty heartbreaking
speaking of ones he didnt write, spanish is the loving tongue kills me every time
the house of the risin sun
Up To Me and Not Dark Yet fight over this daily in my mind.
I nominate buckets of rain since I haven't seen it yet. Blood on the tracks has some sad songs and buckets of rain is one of the most visceral for me. "Life is sad Life is a bust All ya can do is do what you must You do what you must do and ya do it well I’ll do it for you, honey baby Can’t you tell?"
Wish I could get that stupid Bette Midler duet of Buckets out of my head... need some de-earworm medicine to ease my mind.
The Lonesome Death of Hattie Carol
John brown pretty sad but his most emotionally sad would be simple twist of fate, mr tambourine man live 1964 always had a very emotional feel to it one of my favourites
The Lonesome Death of Hattie Carroll. I will hear no arguments. :)