Saddest songs


Jan 12 2010, 0h31

For the past fourteen years (since I started using Napster in middle school), one of my persisting online preoccupations has been finding cripplingly sad songs. The kinds of songs most people generally avoid, outside of awful circumstances and situations of extreme duress. On the other hand, there are those who can listen to little else. In either case, I thought this might be a thing worth sharing. One thing I've found to be true is that there isn't a great deal of overlap in the kinds of songs different folks find to be sad. There are infinite shades of sorrow, and although the soul-broken depression of Jandek's "Down In A Mirror" is pretty far-flung from the simple sadness found in a song like Jewel's "You Were Meant For Me," there isn't anything more real/legitimate/"authentic" about one or the other's sadness. Jewel and Jandek are both going to die. We're all going to die, and there's nothing any of us can do about it. I've done my best to include the saddest songs of every genre and every kind of sadness, without prejudice. With that preface, the list of the saddest songs I know:

Afghan Whigs - When We Two Parted
American Football - Never Meant
Anathema - Are You There?
The Angelic Process - We All Die Laughing
Aphex Twin - Blur, Rhubarb
Autechre - Vletrmx21
Bark Psychosis - From What Is Said To When It's Read
William Basinski - Variations: A Movement In Chrome Primitive - Part 1
The Beach Boys - Caroline, No
Bonnie "Prince" Billy - Careless Love, At Break of Day
The Blue Nile - From a Late Night Train
Broadcast - You and Me in Time
Tim Buckley - Song to the Siren
Burial - In McDonalds
Cage, John - String Quartet In Four Parts
Boards of Canada - Music Is Math, Corsair
Mariah Carey - Breakdown
Carissa's Wierd - Lazy Eyelids, The Color That Your Eyes Changed With the Color of Your Hair, You Should Be Hated Here
Celer - Menggayakan
Tracy Chapman - Fast Car
Codeine - Tom
Cold - Ugly, Same Drug, Strip Her Down
Dashboard Confessional - The Places You Have Come To Fear The Most
Daniel Johnston - Some Things Last a Long Time
Death Cab for Cutie - Sleep Spent
Julie Doiron - Gone, Gone; He Will Forget
Nick Drake - Fly (the Time of No Reply take especially)
Elite Gymnastics - h e r e , i n h e a v e n 2
The Field Mice - And Before The First Kiss
Feldman, Morton - Palais De Mari (for Francesco Clemente)
Fleetwood Mac - Landslide
For Stars - There Was a River
Jackson C. Frank - Just Like Anything
From Autumn To Ashes - Short Stories With Tragic Endings, Autumns Monologue
Ernie (as voiced by Jim Henson) - I Don't Want to Live on the Moon
Grouper - Heavy Water/I'd Rather Be Sleeping, Pulse
Tim Hecker - In the Air III
Don Henley - New York Minute
Hood - Closure, Diesel Pioneers
Interpol - A Time to Be So Small [2001 version]
Jandek - Down in a Mirror
Jesu - Friends Are Evil, Broken Home
Kayo Dot - The Manifold Curiosity
Low - Murderer, Lust
Maёror Tri - These Tears Will Crystallize
Dave Matthews - Crush
Cass McCombs - Saturday Song
The Microphones - Where Lies My Tarp?
Mogwai - Cody, Tracy, R U Still Into It, Hunted by a Freak
Jason Molina - No Moon on the Water
Momus - Suicide Pact
Mount Eerie - Let's Get Out of the Romance, I Say "No"
The Mountain Goats - Maize Stalk Drinking Blood, The Mess Inside, New Britain, Orange Ball of Pain
My Bloody Valentine - No More Sorry
Randy Newman - I Miss You
Roy Orbison - A Love So Beautiful
Jim O'Rourke - Halfway to a Threeway
Owen - Nobody's Nothing
Pärt, Arvo - Silouans Song
Tom Petty - Echo
Rachel's - Falling in With Fire
Radiohead - How to Disappear Completely, Let Down
Red House Painters - Drop, Katy Song, Medicine Bottle
Alasdair Roberts - Ye Banks and Braes O' Bonnie Doon, The Wife of Usher's Well, Lord Gregory
S - Losers, Crushed
The 6ths - Give Me Back My Dreams
Slint - Washer
Slowdive - Machine Gun, Crazy For You, Catch the Breeze
Elliott Smith - Pitseleh, Abused, Can't Make a Sound, I Didn't Understand
The Smiths - Asleep, I Know It's Over
Smog - I Could Drive Forever, To Be of Use, All Your Women Things
The Softies - Hello Rain, Sleep Away Your Troubles
Staind - 4 Walls, Home
The Supremes - Stop! In the Name of Love
Team Sleep - Death By Plane
Telefon Tel Aviv - I Lied
Tiamat - To Have And Have Not
Suzanne Vega - Luka
Venetian Snares - colorless
Tom Waits - Lonely
Gillian Welch - I Dream A Highway
The Wrens - Happy
Xasthur - Masquerade of Incisions, Trauma Will Always Linger
Xiu Xiu - Homonculus, Rose of Sharon (Grey Ghost Version)

If you have anything that you think should be on this list, feel free to write in below. At the end of the day it's still my party, but I give an attentive, honest listen to anything posted.


  • wickedsassy

    That's a great list. Some of my favorites are on there--Gillian Welch and Suzanne Vega, among others. Another good sad song: Beth Orton's version of "I Wish I Never Saw the Sunshine." (

    Jan 18 2010, 15h44
  • markaleksander

    O Death by Sam Amidon. Put that on your list.

    Jan 26 2010, 12h09
  • Indyalanjones1

    Good list. Im surprised theres no bonnie prince billy though

    Fev 10 2010, 20h13
  • UCHalcyon

    @markaleksander: Thanks for the Sam Amidon--I like it, but I don't find it sad. @Last_Years_Man_: I would put much of Townes Van Zandt and American Music Club the 'sad' category, no doubt, but not on the 'saddest' list. Listening to Van Zandt, though, reminds me that Tim Buckley's "Song to the Siren" probably deserves to be on this list. @Indyalanjones1: Bonnie Prince Billy--good point. A song like "At Break of Day," "Careless Love," or even "New Partner" surely belongs on this list. I'll have to go through his catalog again to pick the best one or two. Feel free to suggest. Thanks.

    Fev 11 2010, 0h17
  • Indyalanjones1

    I just mailed you actually...Also Nick Drake should be in there somewhere, maybe 'Parasite' or 'Things behind the Sun'? Now that im thinking about it...The Smiths This Joke isnt funny any more' is pretty sad, as well as This Mortal Coil's version of 'Song to the Siren'. Good shout on the Daniel Johnston choice by the way

    Fev 11 2010, 19h20
  • sunnychick

    Hey. I'm a bit late to the party, but I enjoyed reading your journal. The best journals are always those where someone expresses an opinion or preference and then backs it up. (I rediscovered American Football, which lead me to it). I haven't heard many of the songs you cite, but as you so rightly point out, even if I had, I probably wouldn't find them as cripplingly sad (great expression), as you do. If I were to choose an entire album of complete melancholia it would have to be American Football. I can't think of any other album which is shot right through with so much loss, sadness and regret. Not least The One With The Wurlitzer. Which got me wondering, did you base your choices on lyrics alone or music and lyrics? How can music on its own, as in TOWTW, be so meaningful, and so absolutely heartbreaking? Just thinking out loud... For what it's worth, here are a few of the saddest songs I know: Trembling Blue Stars - Sometimes I Still Feel The Bruise Making contact gets harder As the silence grows longer And why would you think of me When you were not the one in love? When you were not the dreamer? When you were just the dream Dinosaur Jr. - Water All the coolness rushing by Don't let it grab your mind Pull out now or you will find All you strive for Nothing, gone, no more You're his servant now Counting Crows - Mrs Potter's Lullaby I dream I never know anyone at the party and I'm always the host Whiskeytown - Sit And Listen To The Rain Sit around, dream away the place i'm from Used to feel so much, now i just feel dumb Could go out tonight, but i ain’t sure what for Call a friend or two i don’t know anymore Sublime - Garden Grove Waking up to an alarm Sticking needles in your arm Picking up trash on a freeway Feeling depressed everyday Leaving without making a sound Picking my dog up at the pound The quotes are my way of backing up my opinions ;) Cheers.

    Mar 12 2010, 21h01
  • UCHalcyon

    @sunnychick: Not too late at all--I'm glad people are still stumbling across this list. And to answer your question, I definitely chose all of these songs based on the music. There are quite a few instrumentals (the selections from John Cage, Boards of Canada, Morton Feldman, & Rachel's) and a few that might as well be (Kayo Dot, Slowdive, Xasthur). Even in the songs I chose with a strong vocal element, the delivery is much more important than the content. But of course, all of our emotional palettes are built out of our personal history, which is why I'll feel a certain way about some things and you won't! Anyway, there are a few connections to this list in the things you suggest... if you enjoy Trembling Blue Stars, you should really look into The Field Mice, which was Robert's earlier band. Lots of absolute gems on the compilation "Where'd You Learn to Kiss That Way?" Also, I very much share your feelings about American Football--I hope you know that Mike Kinsella is still making music as Owen! If you want something sadder, "No Good for No One Now" is the kind of album that can just break a person. His most recent two, "At Home With Owen" and "New Leaves" are just gorgeous, though. He's one of my favorite artists, so I can't help recommending him enthusiastically! On the note of recommendations: I'm going to make the assumption that anyone who's stumbled across this list looking for sad songs is a person with some kind of emotional perceptiveness. If you want to absolutely treat your senses, I would very strongly recommend you go out and get Joanna Newsom's brand new album "Have One On Me." I wanted to put one of her songs on this list, but struggled to find one that really qualifies as just sad. Each and every one of her songs covers such a range of emotion and feeling that I thought it would be pigeonholing to call a song like "Sawdust and Diamonds" sad, even though there are parts of that particular song at which I absolutely can't hold back my tears. When I first listened to "Have One On Me," I felt a little taken aback--it seemed like is lacked the emotional punch of her previous outing, "Ys." On repeated listens, I realize that I couldn't have been more wrong. I won't tell you what I think the story that arcs over those three LPs means, but I will tell you that it's as heartbreaking as you can imagine. It is certainly worth the repeated listens that it will surely take for you (and me) to mine out the flawless, multi-faceted diamonds of songs she's crafted on this one.

    Mar 13 2010, 23h21
  • TheTom28930

    American Football... BAWWWWWWWWWWWW

    Abr 2 2010, 2h56
  • gracz54

    You might want to check out some of Bark Psychosis' stuff (especially a song called "Absent Friend") - pretty sad stuff, if you ask me.

    Ago 20 2010, 13h54
  • UCHalcyon

    Man am I glad I shared this list. I've been re-listening to Bark Psychosis for days, for the first time in years, and loving it a lot more now than I did then. Thanks so much for all of your comments, everyone!

    Set 15 2010, 10h11
  • ILikeYourSuit

    I think I Hate Myself's Kind Of A Long Way Down deserves to be mentioned. Saddest song I know so far.

    Dez 26 2010, 1h10
  • ILikeYourSuit

    Oh also Daniel Striped Tiger's The Quickest Wit I Can Think Of. I dunno why, but this song depresses the hell out of me.

    Dez 26 2010, 1h11
  • fearimpaired

    Buckley's Phantasmagoria in Two is much sadder than "Song to the Siren" i think :) Both are adorable though...

    Fev 26 2011, 22h03
  • semionato

    i'm crying already. kudos for your choice of the saddest version of drake's fly.

    Ago 4 2011, 5h55
  • IlaiA

    Explosions in the Sky's Your Hand in Mine, sorry for the stranger comment but I found this by mistake and had to write it down :)

    Set 2 2011, 17h16
  • howisya

    excellent work

    Dez 19 2011, 0h07
  • ambiantotaku

    Finally had a chance to go through your wonderful list, my sincere thanks to you for creating this list, and being so generous with it. Indeed sadness has a beauty all of its own. For me, there is nothing more evocative than Jordi Savall & Dominique Fernandez’s - Lachrimae Caravaggio. I would definitely rate it as cripplingly sad. It is no way a secular piece of work, but hopefully that shouldn't impede you in any way, and you can appreciate it for its heart-wrenching sonic beauty.

    Mar 16 2012, 2h33
  • Idiombomberz

    So You Wanna Be A Superhero by Carissa's Wierd should be added, Blackest Bile by Giles Corey, Earthmover by Have A Nice Life. Some more Xiu Xiu couldn't hurt either, Sad Redux-o-Grapher, Don Diasco, or Over Over.

    Fev 7 2013, 17h50
  • Idiombomberz

    Forget Over Over actually, Tonite and Today is more crushing.

    Fev 7 2013, 17h55
  • the_Crowder

    Looks like a great list, will be going through all of it for sure. And lol, "Crush" was the soundtrack of my high school relationship woes. I sometimes miss that teenage hormonal intensity, the highs and lows.

    Abr 6 2013, 17h46
  • sue_denim

    The Antlers "Kettering". Destroys me every time.

    Nov 27 2013, 23h52
  • ambiantotaku

    morganaaa, I wanted to add this to your list The Durutti Column-Never Known Thanks goes to vk for sharing it.

    Set 1 2014, 0h15
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