My friend Kyle and I used to make up these games, in which we would try to list the top ten songs/artists in an invented category, mostly to keep us occupied in the culturally-vacant wasteland that was State College, PA. Often, determining the category was as fun as filling it out, and Kyle was particularly brilliant at category constructions. Some examples: “Top Ten Artists that You Know You SHOULD Love But You Secretly Hate” (Both Kyle and I listed Jim Morrison/The Doors as #1); “Top Ten Great Singers Without ‘Great’ Voices” (I think Kyle said Nina Simone… mine was Leonard Cohen); “Top Ten Rock Anthems” (me: Styx’s “Come Sail Away”, Kyle: The Rolling Stones’ “Paint It Black”). Et cetera, et cetera, et cetera…

Once, Kyle presented the following category: “Top Ten Saddest Songs EVER.” Now, I’m sure you’re thinking that you could easily rattle off ten sad songs without much effort. And, of course, so could Kyle and I. But that wasn’t the point of the game, as we saw it. We took great effort to make sure that our top ten lists only came at the end of much thought and deliberation (and beer). We also were careful that our selections were non-obvious ones. We must have debated dozens of potentially list-worthy songs that night before settling on our ten. I wish I could remember all of the finalists, but I don’t. (I do recall that I cheated just a bit in this category and included one of my own songs, “Heart of Stone.”) However, I have never forgotten Kyle’s choice for #1 Saddest Song Ever… Bob Dylan’s “Don’t Think Twice, It’s All Right.” (That’s a link to Dylan performing the song on YouTube. You should watch it.)

It’s such an obvious selection in some way… and, yet, I doubt anyone with insight, sensitivity and erudition only a hair shy of Kyle’s (which is almost everyone) would have thought of it. The context of Dylan’s story in “Don’t Think Twice” is post-breakup, the perfect mise en scene for sad songs. But instead of a lot of wailing and moaning and gnashing of teeth, its voice is one of (to borrow a trope from Kierkegaard) infinite resignation. The coup de grace comes at the end, after Dylan’s ambling but concise account of the love that was never meant to be. He sings:

I’m walking down that long lonesome road, girl
Where I’m bound, I can’t tell.
Goodbye is too good a word, gal
So I’ll just say fare thee well.
I ain’t saying you treated me unkind.
You coulda done better, but I don’t mind.
You just kinda wasted my precious time.
But don’t think twice, it’s all right.

Ouch, baby. That hurts. That really hurts. It’s just this kind of resignation that captures what is so, so sad about lost loves. And it’s just this kind of attempt at being okay, this shoulder-shrugging stoicism– so earnest and so false at the same time– that drives home the hurt that lies beneath. A masterful song, really.

On a related note, I’ve said for many years that the best songs are sad songs. (That’s why I like country and blues so much.) I’ve never been able to write a “good” song that isn’t generously seasoned with sadness. I just don’t know how to do it. Anyway, I’m opening up the comments section of this post for your additions to the list of “Saddest Songs Ever.” Which tunes tug at your hearts?

17 comments on “Sad Songs Say So Much

  1. Not Chet says:

    perhaps only a personal preference, but kyle once noted to me, while we were listening to “idiot wind” after a long laborious night of drinking at the locust bar, the appearance of ressentiment in the lyrics. to me it seems here present as well, in the “you just kind of wasted my precious time.” which is not ultimately sadness, but anger.

    arguably, of course, sadness and anger are not affects terribly separate. but doesn’t sadness include a sense of resignation alien to anger (and ressentiment) which is what makes sadness beautiful? i’m not sure about that.

    wreck of the edmund fitgerald?
    november rain?
    tainted love?

  2. Not Chet says:

    i’m just kidding about those last ones.

    noentheless, it seems to me imperative to inform you that you will be going to hell for not liking jim morrison and the doors.

  3. Doctor J says:

    I think the song as a whole is meant to be taken ironically… as is the phrase “don’t think twice, it’s all right” most of the time we say it. So, I don’t think it’s about anger… as a matter of fact, the phrasing “you coulda done better, but I don’t mind/ you just kinda wasted my precious time” is intentionally formulated in such a way as to appear NOT angry, just resigned.

    I do agree with you that anger and sadness are not terribly separate. But I don’t think that sadness *always* implies a sense of resignation. For example, I can be sad about a breakup and cover that sadness over with resignation, like when I might say “don’t think twice, it’s all right.” OR I might be sad about a breakup and cover that over with anger, like when I might say “here’s a quarter, call someone who cares.”

    What is similar about the two, I think, is that they both seem *more* sad because the sadness is being displaced, as if it would be too much to handle on its own.

  4. Doctor J says:

    Also, the point of the post’s title “Sad Songs Say So Much” is neither simply to obliquely tip my hat to Elton John nor to cause all my readers to instinctively sing “ooooh, la la la” in their heads.

    The point is that sad songs say so much. So much more than they say, that is.

  5. kgrady says:

    i still find this to be so unassailably the only real candidate that i’m inclined to believe that this song must have played a significant role in constituting my idea of sadness.

  6. Anonymous says:

    Here’s 5 of the top of my head:

    Colin Hay: “I Just Don’t Think I’ll Get Over You”

    Magnolia Electric Company: “Hold on Magnolia”

    Mountain Goats: “Noctifer Birmingham”

    Smog: “Left Only with Love”

    Townes Van Zandt, “For the Sake of the Song”

  7. Doctor J says:

    I want to add Lucinda Williams’ “Those Three Days” to the list. I think it has a similar sentiment to “Don’t Think Twice.”

  8. Anonymous says:

    You took the words right out from beneath my fingertips, doctor j. I was going to add:

    Lucinda William…*Side of the Road*

    But, I’ll also submit:
    Blue Nile…*Because of Toledo*
    Diane Cluck…*Yr Million Sweetnesses*
    Billy Strayhorn…*Lush Life*
    and, perhaps saddest of all for me,
    (?)…*Puff the Magic Dragon*

  9. the songs that make me the saddest are the really sweet ones. like, velvet underground’s pale blue eyes.

  10. Anonymous says:

    i’m with kirsten–who can deal with it when that mighty dragon ceases his fearless roar and bends his head in sorrow? sad, sad, sad. damn you, jackie paper. i’m having a hard time thinking of the saddest songs (maybe it would help if i had some beer), but simon and garfunkel’s “leaves that are green” keeps running through my head–it’s kind of wistful and melancholy.

  11. Anonymous says:

    Crud- “Hold on Magnolia” is on the album Magnolia Electric Company by the band Songs-Ohia (which later changed its name to Magnolia Electric Company).

    As for (Resignation + Sadness) x Anger, try Shellacs “Prayer to God” from 1000 Hurts

  12. Christopher says:

    Tori Amos’ “Northern Lad” is far and away one of the saddest ever.

  13. srv says:

    hmm. for me one of the saddest songs is the red house painters cover of “all mixed up” (by the cars). others that come to mind:
    radiohead, “true love waits”
    eels, “the good old days”
    le mans, “aquí vivía yo”

    -santiago
    http://web.mac.com/svaquera

  14. Anonymous says:

    dr. j: perhaps this has devolved into “Saddest line ever” with that last line of the Dylan song taking the cake. Remember that chorus you told me about in the bar in Chicago, the simple sad breakup line after I told you about “I thought you were so good for me but you’re so so bad.” Anyway, that chorus, whatever it was, was sad.

    But this leads to the difficult problem of the sad song. The obvious sad songs, like chet’s fave, november rain, fail to be sad because they are so obviously sad. Dylan, and I think Leonard Cohen is like this, is sad because he’s so obviously trying not to be.

    Maudlin doesn’t move, but irony does.

  15. Doctor J says:

    bernadette, I can’t remember what song you’re talking about (although I do remember the conversation in Chicago!). Do you remember any part of it?

  16. bzfgt says:

    The saddest song BY FAR by Lucinda Williams is “Metal Firecracker.” Dylan has many other sadsters, such as “Simple Twist of Fate,” “Not Dark Yet,” and the also seemingly-jaunty “Buckets of Rain.” It seems to me that Merle Haggard’s “Today I Started Loving you Again” should make the cut.

  17. bzfgt says:

    Shit, “Love Hurts” by Roy Orbison. I think this was originally by the Everly Brothers, though, whose “Cathy’s Clown” is full of pathos as well. Roy Orbison of course gets mention also for “Only the Lonely” and “Crying.” “When I stop Dreaming” by the Louvin Brothers too. I know it isn’t cool to like the Grateful Dead any more, but “Candyman” is one of the saddest songs, even though if one were to read the lyrics on the page they’d be sheer braggdocio. Bill Monroe’s “Body and Soul” can produce tears.

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