Thursday, January 19, 2012

The saddest songs of all time

These two songs are currently in a dead-lock tie for the saddest song I've ever heard. Notice the common theme: utter and complete subjugation/desperation ("I'll do anything for you"/"I would be anything that you wanted me to be").

"For the Widows in Paradise, For the Fatherless in Ypsilanti" by Sufjan Stevens

"A Favor" by Okkervil River (more on this in an upcoming Coldfront feature)

Same goes for this forever runner-up: "Please, Please, Please Let Me Get What I Want" by The Smiths

Give me your tired, your poor, your most wretched songs of all time.


  1. i used to cry to this song all the time when i was 19. it's still pretty sad.

  2. I don't know if the lyrics qualify, but this is definitely one of the saddest sounding songs ever.

    "Cathedrals" by Jump, Little Children

  3. I got really sick of Sufjan S. and haven't heard any of his stuff in quite a while, but that is certainly a contender for the saddest song title of all time.

    My contribution to the list? Harry Chapin's "Taxi" and "Sequel" (you have to play them back to back for maximum effect) and Richard Buckner's "William and Emily" from his album "The Hill" (which, upon original release contained only one long track consisting of a suite of Spoon River Anthology poems set to music). The re-release gives each segment its own track, sacrificing oblique artistic integrity for ease of listening. Here is the poem, and imagine it with Calexico cello to the gut:
    THERE is something about Death
    Like love itself!
    If with some one with whom you have known passion,
    And the glow of youthful love,
    You also, after years of life 5
    Together, feel the sinking of the fire,
    And thus fade away together,
    Gradually, faintly, delicately,
    As it were in each other’s arms,
    Passing from the familiar room— 10
    That is a power of unison between souls
    Like love itself!

  4. The one that comes to mind right now as the saddest song is "A Long, Long Time" sung by Linda Ronstadt.

    A few runners-up:

    "Since You Asked" sung by Judy Collins

    "As Tear Go By" sung by Marianne Faithfull

    "In My Life" sung by the Beatles

    "Homeward Bound" sung by Simon and Garfunkel

    There was a movie a few years back, "The Saddest Music in the World," set in the 1930's in Winnipeg, about a contest to find the saddest music in the world (hence the title...).

    The music in it didn't strike me as particularly sad, and the movie wasn't particularly sad, though it was one of the weirdest things I've ever seen. And I have a fairly high threshold for weird. Not altogether sure if I liked the movie, as such, but it was unforgettable.

  5. I was just about to ask if you've seen The Saddest Music in the World. A great introduction to Guy Maddin.

    For me, "Round the Bend" by Beck comes to mind.

    And Cole Porter's "In the Still of the Night".

  6. The Lightning Dust song "Days Go By" always makes me cry when it's on my iPod. I have no idea why (I mean, I don't personalize it to any of my own relationships), but for some reason, when it's right in my ears like that, it makes me cry.

    "Bermuda Highway" by My Morning Jacket makes me think of my ex-husband and that used to make me cry.

    "Moonlight Mile" by the Rolling Stones has made me cry when I was driving home through a blizzard at 3AM a few years ago.

    Almost all Sigur Ros songs sound sad to me and when I use them in my yoga classes, I cry while I'm teaching. (People expect it and laugh at me, but the also request these songs.)

    I love a good cry, don't get me wrong. :)

  7. Thanks for all the sad fodder guys, I will be listenin' and cryin' all day tomorrow!

    Lyle, I think Linda's version of "It Doesn't Matter Anymore" is even sadder.

    Some more I thought of:

    "Caledonia" (See

    Redhouse Painters in general


    "Famous Blue Raincoat"

    "People They Ain't No Good"

    "Nothing Compares 2 U"

    "Time of Your Life" (Yes, by Green Day, no joke, this song makes me really sad)

  8. Now I need to do a companion post on the happiest songs. My pick is "New York City" by They Might Be Giants.

  9. Most insanely happy song: "Pop Zeus" by Robert Pollard and Doug Gillard from Speak Kindly of Your Local Volunteer Fire Department.

  10. Hey Dan - nice to see Doug mentioned here!

    Even though it's not a 'song, the Gymnopedies by Satie always make me melancholy.

  11. oh man, how could i forget "Skates" by Hayden...

  12. There are some very sad songs on Lucinda Williams' album Sweet Old World, particularly the title track and "Little Angel, Little Brother." They used to be hard for me to listen to.

  13. Songs about brothers always make me sad. See "Brothers on a Hotel Bed," "The Predatory Wasp of the Palisades Is Out to Get Us" and "Blue Ridge Mountains" as further elucidated here:

  14. I'm ambivalent about Joanna Newsom overall, but her song "Sadie" inevitably reduces me to tears. I'm not even going to listen to it now, before I post it because I don't feel like crying at the moment:

  15. Okay, so happy songs --

    Again just offhand, a tie for the two happiest ones: "Joy to the World" sung by Three Dog Night, and "Celebrate" sung by Three Dog Night.

    "Out My Back Door" sung by Creedence Clearwater Revival.

    "Mercedes Benz" sung by Janis Joplin.

    "Annie's Farm" sung by Taj Mahal.


    "Mellow Yellow" sung by Donovan. (How could I not?)

  16. Marissa Nadler's cover of Famous Blue Raincoat is sad. :)

  17. Happy songs depress me.

    "Famous Blue Raincoat" is sad--sad in French, too: I find "Chelsea Hotel #2" even sadder. "So Long, Marianne" can make me tear up, too.

  18. Many "happy" songs depress me too, mainly I guess because they seem insipidly so. Sad songs can convey at their best an astounding depth of emotion; happy songs, to me, seem forced or trite. But then there are the songs that make ME happy, which aren't always "happy songs". The song I mentioned above is more nonsensical than anything (or so full of in-jokes as to be nonsensical). But the spirit of warmth and enthusiasm always puts a smile on my face, whereas Stevie Wonder's "You Are the Sunshine" (for instance) leaves me feeling nothing except bemused.

  19. There's a happy--albeit slightly dark and sinister--song by The 13th Floor Elevators called "Rollercoaster." It reminds me of Nietzsche's definition of happiness as the feeling that power is increasing, that resistance is being overcome. I like it. The lyrics are good. I like psychedelic rock in general.

  20. One song I would pick for happiness would be the one Woody mentions at the end of Manhattan as a reason for living--Louis Armstrong's recording of "Potato Head Blues". Lots of New Orleans jazz from that time would qualify, and Django Reinhardt. And a lot of traditional Irish music strikes me as extremely happy.

    But my favorite happy song of all time might be "It's a Good Day" by Peggy Lee:

  21. Music like this makes me breathe shallow. It is a blissful feeling.

  22. Tori Amos also has a very sad cover of "Famous Blue Raincoat." Ditto for The Cure's "Love Song." And I like Rufus Wainright's cover of "Chelsea Hotel."

    Happy music is tough -- you have to get it just right. In general, I'm not interested in musicians who write mostly happy songs.

    A semi-sad song that makes me really happy, for some reason, is "Ain't No Sunshine." Heard it yesterday while I was getting my haircut, and had to use serious restraint not to sing along to the "I know, I know" section.

  23. Oh, and more happy-making songs: "Back in Baby's Arms" and "Tra La La Triangle" by Patsy Cline.

  24. A sad song that makes me happy: Leslie Caron singing "Hi Lili Hi Lo." To a g-d'ed puppet, no less.

    A happy song that sounds kinda sad: the Fruit Bats' "So Long." An upsetting song that sounds happy: Lily Allen's "LDN."

    Michael Franti's "The Sound of Sunshine" is happy in a Pop Tart commercial kinda way.

    "Never Seen Blue" by Tori Amos always struck me as sad.

  25. Oh! Another super-sad love-song: "When Your Mind's Made Up" from the Once soundtrack

  26. Also, I have some Django Reinhardt records that absolutely refuse to let you be sad.

  27. Patsy Cline! Love her.

    Everything by Laura Nyro makes me feel like crying.

    The whole Velvet Underground & Nico album makes me pleasantly melancholy. Especially when Nico sings like a dark Gothic tower.

    Dylan has a beautiful rendition of "Man of Constant Sorrow" on his eponymous first LP. It invariably moves me.

    The theme song for The Mary Tyler Moore Show melts my heart.

  28. sad: catch the wind--donovan
    happy: carey--joni mitchell (my kind of happy, anyway)

  29. Pavement's cover of "The Killing Moon" is pretty sad to my ears. I also vote for "Past, Present and Future" by the Shangri-Las.

  30. But seriously, here are the two saddest songs: "Love Is Everything" by Jane Siberry ( and "A Way Out" by Peter Hammill (

  31. Pavement was good at sad. There're some sad pretty ones on Terror Twilight: "Ann Don't Cry," "Major Leagues." "Spit on a Stranger" feels a little sad to me.

  32. Dear Elisa, wasn't going to comment on this but what the hey.

    I think I wrote something recently over on John Gallaher's blog, or maybe it was here, about sad songs, Al Stewart coming to mind for me, etc., and if I remember correctly it was tied to place, or places, particularly the most particular ones, places/contexts always being part and parcel of the best sad songs.

    I don't have a sad list, but if I did, it would go on ... and on, Garden Party would be there, of course, that amazing three second pedal steel solo, and who could ever leave off Puff the Magic Dragon, scratchy vinyl, ten dollar turntable, circa 1964, basement house in central Nebraska, oh.

    One of the happiest songs I know could also find a place very easily atop someone else's sad list, if that says anything. It's by the Pogues, a song called Tuesday Morning.



  33. Also, meant to say something about instrumentation/voice, the whole Steve Martin quote about not being able to play a sad song on the banjo.

    I agree with David about the Nico/Velvet Underground sound. Same for Richard/Linda Thompson. Actual lyrical subject, as several responders note, seems to have little or no connection at times to mood invoked.

    Regarding sad, Cat Power comes to mind, Mazzy Star, as well as the more obvious folks, Elliot Smith, etc.

    Age/maturity plays a part as well, I suppose. I recall a song from high school, early 70s maybe, Seasons in the Sun, by Terry Jacks, I think, or someone, that tugged pretty heavily at the heartstrings years ago, but hearing it more recently was kind of a cringeworthy experience, to say the least.


  34. On youtube you can find Nirvana playing "Seasons in the Sun." Interesting.

  35. Interesting. The TJ version of Seasons in the Sun seems to be almost dripping with sap, but I might still like a Nirvana version.

    Nirvana certainly fits in the sad section (All Apologies is a favorite) but can quite as easily bridge a wide range of emotion.

    This thread also reminded me of Mountain Goats 'Pale Green Things' and had me going back to listen to some great Mark Linkous/Sparklehorse songs, kind of a downer, a good downer, I guess, nothing I hope the harmonica solo from The Romantics 'What I Like About You' can't cure.



  36. Re lyrics, yes, John and I listened to Linda Ronstandt's version of "It Doesn't Matter Anymore" contrasted with the original Buddy Holly recording or the Wanda Jackson version, both of which are upbeat and kind of goofy.

    Nirvana's whole Unplugged album is pretty sad.

  37. I am old but sadly not wiser. Listen to words of Matt Munro's Walk Away and Softly. If that doesn't move you I might as well give up now.

  38. Johnny Cash "I hung my head" always used to mist me up, still gives me chills whenever he says "i orphaned my children, i widowed his wife." Man and something about that piano, sounds just as dynamic and insistant and mournful as his Hurt cover not Hurt.

    In content Cash's "he stopped loving her today" is also pretty sad but...definitely doesn't compete musically.

    Sure hope you aren't indulging ALL the downers showing up in these comments, hoo boy!

  39. I don't know Cash's "He Stopped Loving Her Today," but I know George Jones's. G. J.'s voice appeals to my maudlin sensibility.


    kinda this whole album
    won an oscar..Once the soundtrack

  41. The seems the saddest on the album...sorry should have put above..

  42. Hurt done by,Johnny cash before he died, and Bonnie Raite and Lyle Lovitt Angel of Momtgomery, and of course John Prine, there's a hole in daddy's arm where all the money went,,, just shoot me!

    1. my boyfriend does a great karaoke rendition of Johnny Cash's version of Hurt.