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Dude-WhatIfZombies

Sam Stone, by John Prine But only if you want the very saddest.


mdibah

See also "Hello in There," "Souvenirs," "Summer's End," ...


iambobanderson

+1 for hello in there šŸ’”


XP_3

Sad doesn't do it justice, heart wrenching.


mcluhanism

A different type of sadness maybe, but a great "sad sounding" song also by John Prine is ...Ā  The Lonesome Friends of Science.Ā  He has a bunch that would fit this thread actually.


ELH13

Angel From Montgomery and Summers End too


tire_swing

Also 6 O'clock news by John Prine. Gives sam stone a run for its money.


Pepperonimustardtime

Also Clay Pigeons - John Prine. Love his version of it.


hvacmac7

Wow manšŸ˜“


Idlers_Dream

Gillian Welch - Tennessee


nobodyspecial9412

Playing this one now. ā€œNow Iā€™ve tried drinking rye and gambling / dancing with damnation is a ball / but of all the little ways Iā€™ve found to hurt myself / well, you might be my favorite one of allā€ hits fucking hard. Perfect recommendation for what I was looking for, thank you!


KrasnyRed5

Just pick anything by Gillian Welch. It's all good.


Totekk03

Seconded. The Way That it Goes or Hard Times would be great next listens.


KrasnyRed5

Tear my Stillhouse Down is a special favorite of mine.


nobodyspecial9412

Definitely want to listen to her more. I love ā€œWrecking Ballā€ and definitely liked ā€œTennesseeā€ so canā€™t wait to hear others!


KrasnyRed5

Her cover of Scarlet Town and Tear my Stillhouse Down are a couple of my favorites.


TheJamMeister

"Orphan Girl"


MisterBiscuitz

ā€œOur Townā€ by Iris Dement


payasopeludo

I love this song


nobodyspecial9412

This one slaps, thank you.


[deleted]

"The Blower's Daughter" by Damien Rice "Naked As We Came" by Iron & Wine "To Be Alone With You" by Sufjan Stevens


TerminatorAuschwitz

Naked as we came in actually one of their less sad ones imo. The trapeze swinger always makes me cry tho.


Pepperonimustardtime

Man I was really hoping to see all three of these artists here. And amazing choices for all three. I would also add Cannonball andĀ  The Professor La Fille Dans by Damien Rice. Both so keeningly sad and regretful.


Think_Smarter

Folk ish? Americana? If we were Vampires by Jason Isbell. The Curse by Josh Ritter. Cranes of Potter by Charles Wesley Godwin


Bosgarage57

Elephant by Jason Isbell is heartbreak as well.


brettjv

Damn near all of the Southeastern record fits the bill.


brettjv

Also: Josh Ritter - Kathleen


FreiyaFox

Nick Drake - Pink Moon Neil Diamond - If I dont see you again Joan Baez - Diamonds and Rust Leonard Cohen - Avalanche


jsalfi1

ā€œFruit Treeā€ is another sad one I enjoy by Nick Drake


Chiperoni

And *Parasite*


8805

Vincent Black Lightning 1952 by Richard Thompson https://youtu.be/j0kJdrfzjAg


13eco13

I was actually just thinking this when I was scrolling the list!


hairyminded

Incredible song


bamsuckah

ā€œBroad Ripple is Burningā€ by Margot and the Nuclear So and Soā€™s


tintedrosie

Gosh I love that band. Also check out their song ā€œTalking in Codeā€.


lastgirlonEarthh

Oh my god I havenā€™t heard this song in so long thank you for reminding me of its existence.


[deleted]

Guess Iā€™m Doing Fine - Beck


letmebebrave430

Sounds like you'd enjoy most of Lord Huron's discography! They're The Band of lost love and wandering. Specific recs: Twenty Long Years The Ghost on the Shore The Night We Met Wait by the River Frozen Pines And my favorite: What Do It Mean


xxotwod28

Lord Huron gives me emotions no other band can!! These are all great reccomendations & I havnt stopped listening to frozen pines all month!


The_Velvet_Bulldozer

[Hellā€™s Canyon](https://youtu.be/joowhQfTFyo?si=Sjf4F0895vkrimx9) - Lost Dog Street Band [Manitoba Man](https://youtu.be/SKPMqAqsTO4?si=9RLWcDxkV2G8GfUq) - Colter Wall [Marie](https://youtu.be/Lk-zKjfO2E8?si=GKwN05H4dXkkV7-6) - Townes Van Zandt [Fare the well (Dinkā€™s Song)](https://youtu.be/7M8m4LyFSkE?si=f1uiyIHKQm2jKTq0) - Oscar Isaac


nobodyspecial9412

Love ā€œThe Devil Wears a Suit and Tieā€ and ā€œMotorcycleā€ by Colter Wall. Listening to Manitoba Man nowā€”definitely dig it! Thanks for the rec!


bob_doolan

Check out Frank Turner! His first several albums fit your description nicely. He leans into punk quite a bit, but songs like Wanderlust, Redemption, St Christopher is Coming Home, Tell Tale Signs, Anymore, and Nights Become Days are folkier and either melancholy or sad.


TheeFlipper

Wildfire by Watchhouse(formerly Mandolin Orange) San Luis by Gregory Alan Isakov Using Again by Benjamin Tod


usernamerevoked

And pretty much any by Benjamin Tod, but this is probably the saddest. Big River Ballad is close too.


theclownwithafrown

Mandolin Orange is one of the best bands of all time.


ThirstyRhino

First day of my life - Bright eyes


GoodOlSpence

I just saw [Jason Isbell perform on The Daily Show](https://youtu.be/bhOLnYatPeA?si=QOfti-t4dMiHkLKn) and it broke me pretty good.


ss_lbguy

Elephant by Jason Isbell. Listen to the entire southeastern album.


Oh_Django

Some of my favorite songs of all-time: [John Lennon - Working Class Hero](https://youtu.be/HmhLsE5woRw?si=YptEdXOZmbAgqoad) [Modest Mouse - Lives](https://youtu.be/mb-t_TegR-Q?si=nQoeCpvrU0-Lfm0r) [Mitski - Iā€™m Your Man](https://youtu.be/HvgX44ESvHQ?si=7u6B-Au4d3SM2LQK) [The Mountain Goats - No Children](https://youtu.be/QS27S3mspjU?si=m8DUOV-2FzFz8zSZ) Enjoy your depression


jsalfi1

Modest mouse and tmg are my favorite bands - thanks for sharing


johangubershmidt

Sad Snack did a ska version of No Children that's really good if you're into that kind of thing


TheMagicBarrel

ā€œNeedle in the Hayā€ by Elliott Smith


Dude-WhatIfZombies

Also ā€œBetween the Barsā€


[deleted]

"These Days" either the Jackson or Nico version...


nobodyspecial9412

Love Jackson Browne & his version of that song. Will have to check out the Nico version. Thank you!


mamacrocker

Dawes also does a great cover of this!


tangerinerocketship

Cat Powerā€™s version of this is good also


BobDobFrisbee

ā€œA Better Place To Beā€ - Harry Chapin


merft

Came say say this and "Corey's Coming" - Jim Croce "Mr Banker" - Lynyrd Skynyrd


avec_serif

ā€œSeven Cursesā€ is the saddest Dylan song of all


nobodyspecial9412

I didnā€™t know this one, definitely enjoying it. Thank you!


stutterstut

'Tecumseh Valley' by Townes van Zandt. Nanci Griffith did an excellent cover of this song.


winothirtynino

I mean,Ā  Puff the Magic Dragon is about the saddest song ever.Ā 


albertogonzalex

I see a darkness by Bonnie Prince Billy https://youtu.be/5mpo9UYl_Yw?si=-3e0-KgV-2_i0pig


SomethingClever70

Where Have All the Flowers Gone? - by Peter, Paul and Mary. The lyrics were adapted from a Cossack folk song.


Lycaeides13

I'm only familiar with the Kingston trio version


N0TAn0therUs3rNam3

Ballad of Hollis Brown.


nobodyspecial9412

I know that one. God-tier song. Unbelievable Dylan was in his early 20s when he wrote it.


WakingOwl1

Cold Missouri Waters. True story about a forest fire jump crew that gets trapped fighting a fire, killing most of them. Itā€™s told from the point of view of their crew chief years later as heā€™s in the hospital dying. The original by James Keelaghan https://m.youtube.com/watch?v=Dztj4X3fQps My favorite version by The Paul McKenna Band https://m.youtube.com/watch?v=-fyu0LQS05I


mdibah

I'm partial to the version by [Cry, Cry, Cry](https://youtu.be/VxDV2nvk9pM), a supergroup composed of Dar Williams, Lucy Kaplan sky, and Richard Shindell. The whole album is absolutely worth a listen!


Unevenviolet

And anything by the Decemberists. Owwww.


gabeuscorpus

Notable mentions: Eli the Barrow boy Hazards of Love #4 Don't Carry it All Mariner's Revenge Song


brettjv

>Cause I caught you and I > >Brought you here > >These Hazards of Love > >Nevermore will trouble us I love HOL 4 (The Drowned) so much. KILLER song. And it's so genius at the end of the (overall great) album. Just a perfect closer. And every song on The King is Dead is a straight-up gem. June Hymn is my favorite, but they're all great.


Cindylana

ā€œOperatorā€ by Jim Croce


nobodyspecial9412

Great recā€”Iā€™m loving this one. ā€œI only wish my words could convince myself / that it just wasnā€™t real / but thatā€™s not the way it feels.ā€ Wow. Thank you!


ojitar

That whole album is good. Honestly.


spaniel_rage

"The Partisan" Leonard Cohen


ELH13

Also: Avalanche, The Stranger Song, Famous Blue Raincoat, and Teachers


CMJMartino

Check out all by Eva Cassidy. She was amazing! Also Jeff Buckleyā€™s album ā€œGraceā€ will change your life.


usethe4th

Eva Cassidyā€™s covers make you feel like you are hearing familiar songs for the first time. She was incredibly gifted.


TheJamMeister

Eva's version of *Danny Boy* is a real sob-fest.


bikewizard

Evaā€™s voice and playing is incredible. You can hear the sadness in her voice. Her version of Gas Station Mountain Home is so heart felt. It makes you feel that was her life. So many other great choices within here songbook!


ShamefulWatching

Most songs by Lost Dog Street Band, hard luck songs you might say. Then there's a handful by John Prine:Sam Stone being a pretty sad one, Me same Loretta also


urbanek2525

The Weary Kind by Ryan Bingham


close_my_eyes

Blood and Fire by the Indigo Girls.Ā 


CoachDonut82

John Moreland - Gospel; 3:59 AM; Blues & Kudzu; American Flags in Black and WhiteĀ  Gabe Lee - Lidocaine Ian Noe - Junk Town Ryan Culwell - The Last American John R. Miller - Faustina Michigan Rattlers - Evergreen Nathaniel Rateliff - And It's Still Alright


shakrbttle

Just saw Nathaniel Rateliff the other night and absolutely sobbed through And Itā€™s Still Alright. Had to sit down for the song after to compose myself. I didnā€™t expect him to play it and as soon as the first ā€œbackgroundā€ guitar sound hit my heart sank.


wolfpack_fan

Jason Isbell, take your pick


demasoni_fan

Ani DiFranco has many, I think two of her saddest are "School Night" (the second verse is a Sophie's Choice theme) and "Letting the Telephone Ring" (she's bi for context). For a sad addiction song - about someone else - she has "Come Away from It". "Stay Down" by boygenius. If you want songs about drinking and addiction check out Julien Baker's music (a member of boygenius, the one singing that song).Ā  "Getting Over You" by Melissa Ferrick. It's not her saddest song but I love her playing in it. She has songs about letting go of drinking too - "Bad Habit". "Simple Together" by Alanis is a devastating break up song. "Jackson" by Lucinda Williams, about travelling and missing someone.


MiniRipperton

Revelling/Reckoning just destroys me. And especially School Night. What kind of scale, compares the weight of two beauties? The gravity of duties, or the ground speed of joy? Tell me, what kind of gauge can quantify elation? What kind of equation could I possibly employ?


brownbear8714

A girl I was friends with in high school loved Ani DiFranco. Never really got into her but maybe I should check her out again. Boygenius is really good and Julien Baker is a stud. I like her solo stuff a lot too.


Best-Training3410

Ride On by Cristy Moore is an all time classic! [https://www.youtube.com/watch?v=E-z7M3FZv4E](https://www.youtube.com/watch?v=E-z7M3FZv4E)


Blackened-One

ā€œEnough Ropeā€ - Chris Knight


nobodyspecial9412

Digging this oneā€”thank you!


jorgofrenar

Never coming home (song for the guilty) by Pat the bunny


OuijaSin

Willi Carlisle. All his stuff which is still fairly limited since he's kinda new. Singing Knives or Angels are good


Totekk03

Disc 2 of the Tom Waits album Orphans is called ā€˜Bawlersā€™ and features a bunch of his downbeat stuff. I like to play the whole album but if I had to pick one Iā€™d say maybe You Can Never Hold Back Spring.


winothirtynino

Peter Paul and Mary 500 miles always makes me sad.Ā Ā 


marcosbowser

More Blaze Foley, like Picture Cards Canā€™t Picture You


tastesoff74

The White Buffalo - Ballad of a Deadman, Dirty Old Town - The Pogues, Cumberland Gap - David Rawlings


Flashy_Sleep3493

[Same Old Lang Syne - Dan Fogelberg](https://youtu.be/cfAxWtcfDUk?feature=shared)


down-with-homework

Waiting Around to Die by Townes Van Zandt


nobodyspecial9412

First Townes song I ever heard. Came up in my Spotify shuffle and immediately changed my life. I became obsessed with Townes there and then. Great fucking song.


johnwongfat

He's a contemporary artist, but I would highly recommend Amigo the Devil. His new album just dropped yesterday, and it's fantastic. It sounds like Cocaine and Abel, Another Man's Grave, or Different Anymore would be the kind of stuff you're looking for. His music ranges from straight depressing, to hilarious. Bonus points if you're into serial killers. He has a LOT of serial killer themed tracks.


Kid520

So glad to see Amigo mentioned. I was gonna recommend everything is fine. I've been following him since he played sets between sets at metal festivals. First time I saw him he was playing in a venue bathroom.


BeachedBottlenose

Will Hoge - Goodnight/Goodbye


nobodyspecial9412

Cozied up in my apartment with a drink giving these suggestions a listenā€”I like this one a lot, thank you!


BeachedBottlenose

Someone suggested that to me years ago when my ex and I were going through a bad time. Hits hard. Hang in there.


GhostNote_

Lots of older Beck stuff. Hard to Compete https://youtu.be/MJWmG9Ns4XE?si=ju98tUqN_00TGTAr The Way it Seems https://youtu.be/E17ETCHfmy8?si=MUbiZS2ipjGRd6ul Spirits https://youtu.be/wOtnFevcPLU?si=8D5ZeTcntOxhkoCH Curses https://youtu.be/SON8XEv3q0M?si=uz81_NcFI1q5rMAw The Land Beyond https://youtu.be/OagErWacL0E?si=a145Wq1e-iupGQQY


jamseph

Joe Purdy might be something you'd be interested in. I'm not familiar with a lot of his discography, but the album "Canyon Joe" is pretty sad.


usethe4th

I used to listed to him a lot, and he just started reappearing on my Apple Music station over the last week. I met him a few years ago and he was a very kind guy. I had a pass to a film festival and noticed that he was the lead in one of the movies. I went to see it and he was there! He played a few songs after the screening and it was lovely.


etherealveritas

Not sure if these count lol ā€œBottom of The Bottleā€ by Jack Kays, ā€œBoiled Frogs - Live @ The Vergeā€ by City and Colour, ā€œStick Seasonā€ by Noah Kahan, ā€œObligatory Folk Punk Songā€ by Pancciā€™s Pizza


Dragontoes72

The pines


Caliastanfor

Lime Tree - Bright Eyes


NeitherSwimSorry

Idk if I can comment my own track but I write sad folk music! I have one track on Spotify itā€™s called: pillow marks on your face - Jose Daniel Itā€™s the first song I released and I really draw from Simon & Garfunkel, Sufjan Stevens etc. just trynna make lonely music for lonely hearts


nobodyspecial9412

Absolutely appreciate you sharing your own track, Iā€™ll check it out!


Orginizm

Garden of leavin - Amigo the Devil. It's new, like released Friday new. It'll wreck you


nobodyspecial9412

Playing this now. Wow. Heavy shit. Definitely the thing I was looking for, thanks for the rec!


dangerous_strainer

I recommend this album by Hayden. If it doesn't get you by the first song then you're not looking for sad folk music. https://www.youtube.com/watch?v=D3cr9Pwuwq0


Megmuffin102

Good lord do I love this song. Iā€™ve only ever met one other person that knows it.


hobo_fapstronaut

Beeswing by Richard Thompson > Oh, she was a rare thing, fine as a beeswing > And I miss her more than ever words can say > If I could just taste all of her wildness now > If I could hold her in my arms today > I wouldn't want her any other way


dthains_art

The Avett Brothers have some good stuff. ā€œMurder in the Cityā€ and ā€œIn the Curveā€ are 2 off the top of my head.


PIDDYPUFFPUFF

ā€œHurtā€ the version by Johnny cash


johnwynnes

"The Arrangements" Willi Carlisle


OuijaSin

I saw Willi recently in Michigan and yeah he's among my favourite artist's right now


Thealien102095

ā€œCorrido Por Buddyā€ by Jolie Holland


BlackBoxFox

"Have you seen Joe?"- Blind boy music


thesean366

Stinking of Whiskey Blues - The Ergs Cheating at Solitaire - Mike Ness


nobodyspecial9412

Stinking of Whiskey Blues is great. Thank you!


anarchypicnic

Chasing After Deer by Midlake


cemaphonrd

Trad murder ballads like ā€œDown in the Willow Gardenā€ and ā€œBanks of the Ohio.ā€


77chinook

Every Loser Needs A Mother - Sarah Mary Chadwick


GitchigumiMiguel74

Soon This Space Will Be Too Small, Lhasa de Sela Nick Drake, Black Eyed Dog Jamie Commons, Lead Me Home Down The Line, Jose Gonzalez Words, Gregory Alan Isakov Words https://g.co/kgs/cwGmx1F


calvinwho

No Children by The Mountain Goats


Bone_Dogg

Someday Soon - The Trouble With Templeton


KrasnyRed5

I Remember You - Eilen Jewell.


deltaechobravo

Springhill Mine Only our rivers run free King's Song


Howie773

Song for Sid Langhorne Slim was at a small concert of his ,he started this song every guy around me " that song is about my father or that song is about my grandfather " they were all wrong it was about my grandfather


ojitar

Iā€™ve got this little lovely list I made a few years ago. I expand on it from time to time but I find all these songs fit your bill. https://open.spotify.com/playlist/5WYdasH9ob8wxYOMXIUJYe?si=moULoJWVTjCBIM5yy-SOwg&pi=u-bv0mEts5SYeY


cookerg

The Lament of the Irish Immigrant - the Rankin Family.


ctdrever

Long black veil. JGB


TraditionalWinner193

one too many mornings -bob dylan


Tumblebug_bumpercars

Many many versions of this traditional song, The Loverā€™s Ghost, [but I love this version by Alasdair Roberts the most.](https://youtu.be/k-H2rOGgtBc?feature=shared)


sad-dave

Sad Blue Eyes - Jeffrey Martin


acatmaylook

You'll Never Leave Harlan Alive - Darrell Scott (or the Patty Loveless version is good too and arguably more folky-sounding) Jason Isbell - Elephant, If We Were Vampires, Traveling Alone Josh Ritter - All Some Kind of Dream, Girl in the War, maybe Thin Blue Flame (side note, he's one of my favorites ever and I wish he were more well-known!)


nobodyspecial9412

Know the Isbell songsā€”seeing him with my parents in a couple weeks in fact! But I donā€™t know the others, so thanks for those, will check them out.


Bosgarage57

"golden Embers" by watchhouse "stone walls" by three tall pines "St Thomas" by Ben Heckler "sorry for the things" by Benjamin tod 'hell and you" amigo the devil


kizmitraindeer

[Dublin Blues - Guy Clark](https://open.spotify.com/track/4rXt1tYHZIavECuN32fk96?si=knF_Me4rQTemzwlXPjvTWA) (hope that qualifies)


davFaithidPangolin

Check out Sufjan Stevenā€™s album Javelin


Desperate_Ambrose

"Kilkelly" \~ [https://www.youtube.com/watch?v=dVWUth6SjlU](https://www.youtube.com/watch?v=dVWUth6SjlU) "Crooked Jack" \~ [https://www.youtube.com/watch?v=gZMf\_8BfvjE&list=OLAK5uy\_n3eZVM-hjaHw\_PVjx7jQHLi4I1G7NY5YE&index=13](https://www.youtube.com/watch?v=gZMf_8BfvjE&list=OLAK5uy_n3eZVM-hjaHw_PVjx7jQHLi4I1G7NY5YE&index=13) by Colcannon


000ArdeliaLortz000

The Sound of Silence, Simon & Garfunkel.


nobodyspecial9412

Hm, Iā€™ve never heard of this. Is it famous or something?


kingsss

Graveyard - The Devil Makes Three


Totekk03

Milk Carton Kids - Snake Eyes Shovels & Rope - Swing Low


gtautumn

William Elliot Whitmore - Porchlight


leopardskin_pillbox

Old Barns - Greensky Bluegrass


The_Bluejay250

casimir pulaski day - sufjan stevens this artist is a whole ass rabbit hole iā€™m currently too tired to walk you through but at least listen to this song, and/or look up his saddest songs


obscuremarble

OP, if you haven't ever listened to Joan Baez, she covered a *ton* of Dylan's songs as he was releasing them and, in my humble opinion, improves upon most of them just by the sound of her voice. She also has lots of self-written folk from the 60s and most of it is sad.


wolphkaat

"Half a world away" and "country feedback" both off of r.e.m.'s out of time


[deleted]

bell bottom jeans - jack van cleaf , he opened for noah kahan and is an incredible wordsmith


sorengray

Purple Mountains is basic a beautiful suicide note. Elliot Smith also hits those sad spots every time


aquay

Fatal Flower Garden - Andrew Bird


miles730

Consolation Prize by Ken Yates


tintedrosie

ā€œComin Homeā€ by City and Colour. It was the old gateway song into his work way back when he wasnā€™t known quite as well. Fits your travel theme idea.


emoooooa

Stick Season - Noah Kahan


Unevenviolet

That Edmund Fitzgerald song by Lightfoot. As a kid always left me with a hollow feeling. Also Nico These Days. Ugh


Philcollinsforehead

Far Away by Jose Gonzales


skippythewonder

Diggin' My Grave- William Elliot Whitmore.


costanzashairpiece

I enjoyed the Into the wild soundtrack by Eddie Vedder. Or the album Nebraska by Brice Springsteen


boyridebike

Atlantic City ā€¦ā€¦ man!!!


mrflibble4747

My Dog has Died and my Wife has Left Me - Unknown (traditional)


mdibah

If you're looking for sad folk-adjacent songs, ain't nothing better than OG delta blues. [Mississippi John Hurt](https://youtu.be/w24DE1Egp1Q), [Lead Belly](https://youtu.be/xn50JSI0W-E), [Blind Reverend Gary Davis](https://youtu.be/CGDZdy8lDmc), [Robert Johnson ](https://youtu.be/YYsnRc09csQ), [Muddy Waters](https://youtu.be/3INGas43OF0), ... Gotta live the blues if you wanna sing the blues


optmsrhyme

The Throes- Two Gallants


llamallama29

Soldierā€™s joy, by guy Clark


Friggin_Grease

This song from Red Dead Redemption 2 gets me every time. https://open.spotify.com/track/6wMkJ6KmhuN1oe1Kvtz7PN?si=73XWyCokQdWj_sGYQ7k9fQ


DeadTorturedPoet

She/He Moved Thru the Fair breaks me every time. Especially SibĆ©alā€™s version


SuperDiscoBacon

For more modern ones I'd recommend a bunch by First Aid Kit, in part their album Ruins which was written after a break up. Songs in particular are - "To Live a Life" "Fireworks" "Hem of Her Dress" "Postcard" "Nothing Has To Be True" Also their song "Ghost Town" from their first album is beautiful and sad


shanebonanno

You might already know this one because Dylan covered it. But moonshiner, a traditional Appalachian tuneā€¦ so somber and yet so upbeat at the same time. Makes me wonder who wrote it and what they were going through at the time. Somehow truly timeless and at the same time relatable to the modern man. There is a reason this song persisted through time.


ELH13

Justin Townes Earle - Slippin' and Slidin', Lone Pine Hill, Yuma, Appalachian Nightmare, and Mama's Eyes. Magnolia Electric Co. / Songs: Ohia - What Comes After the Blues, Farewell Transmission, The Dark Don't Hide It, I've Been Riding With The Ghost, The Night Shift Lullaby, Little Sad Eyes, and Just Be Simple. Gordon Lightfoot - The Wreck of the Edmund Fitzgerald. Elliott Smith - A Fond Farewell, Needle in the Hay, Somebody That I Used to Know, and Angeles. Bright Eyes - Haligh Haligh A Lie Haligh, Flirted With You All My Life (Vic Chestnut cover), We Are Nowhere and It's Now, Sunrise Sunset, Something Vague, and Poison Oak. Tim Buckley - I Never Asked To Be Your Mountain, and Grief in my Soul. Sarah Shook and the Disarmers - Heal Me Bon Iver's debut album. Nick Drake - Pink Moon (album). Beck - Nobody's Fault But My Own Graham Nash - Better Days, Sleep Song, and Wounded Bird. Uncle Tupelo - Moonshiner Lucinda Williams - Drunken Angel (Hurray for the Riff Raff do a great cover). Neil Young - Needle and the Damage Done, Old Man Sharon Van Etten - Every Time the Sun Comes Up Jackson Browne - Late for the Sky, Before the Deluge, Fountain of Sorrow, and For a Dancer. Gillian Welch - Strange Isabella, Everything is Free Bonnie Raitt - I Can't Make You Love Me


[deleted]

[уŠ“Š°Š»ŠµŠ½Š¾]


TipsyMcStagger206

Take Me Home by Ocie Elliott


Your_Product_Here

Tom Waits - Martha Red House Painters - Have You Forgotten? (original version, not from Vanilla Sky) Jason Isbell - Cast Iron Skillet, also Elephant John Moreland - Break My Heart Sweetly Joni Mitchell - The Last Time I Saw Richard


Moosey_Bite

For something different, try Over Rainbows and Rainier, by Damien Jurado.


thomasnash

For traditional (british) folk:Ā Ā  - Clark Saunders - Martin SimpsonĀ Ā  - Go your Way - Ann BriggsĀ Ā  - Matty Groves - Fairport ConventionĀ  - Geordie - Anais -Mitchell & Jefferson HamerĀ Ā  - Lovely Willie - Jefferson Hamer and Eamon O'LearyĀ Ā  - The Old Churchyard - Offa Rex Ā  For Country/Americana/Modern Folk: Ā - Shake the Frost - Tyler ChildersĀ  - Life Worth Livin' - Uncle TupeloĀ  - Wildfire - WatchhouseĀ Ā  - Our Remains - Beta Radio Ā Ā Weird/Experimental:Ā Ā  - Sidewalk Bop After Suicide - Cass Mccombs (Kind of psychadelic americana)Ā Ā  - Petals - Bibio (Hip hop influenced folk electronica)Ā Ā  - Sweet William - Tuung (strange folk electronica)Ā Ā  - Go dig my grave - Lankum (Very severe, doom laden trad folk)


astronautmechanic

Yuma by Justin Townes earl


TheScarletFox

Some sad/melancholy older stuff: Ainā€™t Life a Brook - Ferron Inches and Miles - David Mallett Love at the Five and Dime - Nanci Griffith Caledonia - Dougie MacLean Lord, I Have Made You a Place in my Heart - Greg Brown There Were Roses - Tommy Sands Are You Happy Now? - Richard Shindell


Kabc

To build a home - cinematic orchestra On the nature of sunlight Sideways by citizen Cope When a heart breaks - Ben Rector Blackbird song - Lee DeWzye I got a bunch more but those are the ones Iā€™ve been listening to lately Edit: Dreaming tree - Dave Matthews Band Mad World - Gary Jules Digging my own grave - Thrice The Whaler - Thrice Daedalus - Thrice


Chiperoni

*Flirted with You All My Life* - Vic Chestnutt


[deleted]

You recommend several classics. Mine's a bit modern: Bird Stealing Bread - Iron & Wine Malleable Beings - The Paper Kites Tin Lover - The Paper Kites San Luis - Gregory Alan Isakov Was I Just Another One - Gregory Alan Isakov Words - Gregory Alan Isakov The Stable Song - Gregory Alan Isakov with the Colarado Symphony Version If I Go I'm Goin - Gregory Alan Isakov (also listen to the Colorado Symphony Version) Master & a Hound - Gregory Alan Isakov Highway to the Sun - Ray LaMontagne Empty - Ray LaMontagne Words Underlined - Jesse Marchant You Always Keep Me Around - Jesse Marchant Twenty-Twenty Single - Savannah Conley Many more.. Haha


Rudyjax

Warren Zevon. ā€œKeep me in your Heart.ā€


twirleygirl

Have you checked out Robert Plant & Alison Krauss? Their voices are magical together! Two albums: Raising Sand & Raise the Roof All the songs are great, but especially Killing the Blues and Please Read the Letter


Liverpoollarkin

Paradise John prine


Lycaeides13

Rich men north of Richmond -Oliver Anthony Nobody cares - momma molasses Paradise - John prine Sam stone john prine Port coton - zaz (it sounds sad, idk if it actually is in the lyric, which are French)


jiggy68

You Win Again by Hank Williams. Itā€™s about a cheating wife. Heartbreaking song. Keith Richards did a great cover of it on a Hank Williams tribute album.


weaselkeeper

Check out the album ā€œShady Groveā€ by Jerry Garcia and Divid Grisman. They donā€™t really preform them in a sad way but all the songs are at least 100 years old and most end in tragedy.


semper_ortus

People often overlook **British folk,** but there was a lot going on in the 60s and 70s in the UK to dig into. This is one of my favorites on the sad/longing side: **Anne Briggs** - [**Go Your Way**](https://www.youtube.com/watch?v=vS81zHrOB74) If you like that, check out the people who were in that scene - Pentangle, Steeleye Span, Fairport Convention, and various solo artists.


superboofmedia

If you like Clay Pigeons, might be worth checking out [Dark Thing](https://open.spotify.com/artist/06LQKiKHCSjnjfi4twovxV), they have an insanely cool catalogue when it comes to the whole sad folk vibe.