The Saddest Song

 Posted by
Feb 122016

I’ve been learning a bunch of Tom Waits songs and in the course of doing so, some of my cohorts and I began to wonder: what is the saddest Tom Waits song? There are several excellent candidates.
Georgia Lea, for instance, tells the story of a street kid who is found dead in a ditch and asks the question ‘Why wasn’t God watching?”
Alice is sung from the perspective of Lewis Carrol and addresses his inappropriate obsession with the real life inspiration for Alice in Wonderland.
But my vote is for A Little Rain. It’s sung from the perspective of a grave digger who is surrounded by surreal characters. He seems to be trying to keep a stiff upper lip about his general situation, and is thankful that the rain makes his job easier by softening the ground. Then the last verse:
“She was 15 years old
And never seen the ocean
She climbed into a van
With a vagabond
And the last thing she said
Was ‘I love you mom’
And a little rain
Never hurt no one”
But this made me wonder. Is there a sadder song than A Little Rain? It doesn’t have to be restricted to Tom Waits but I’m not talking about some maudlin thing like Seasons in the Sun, or some country weeper where the guy runs over his own hound dog with his pickup on his way back his pappy’s funeral or something. (I suppose “maudlin” is probably in the eye of the beholder and you might consider A Little Rain to be maudlin, but I’m interested in hearing what you consider to be a truly sad song. If your answer is Seasons in the Sun, make your case).
Delivery and nuance seem like critical issues here.
The only one that hits me like A Little Rain is Galveston by Glenn Campbell.
So, what is the saddest song?


  13 Responses to “The Saddest Song”

  1. ladymisskirroyale

    And TGIF to you, too, cdm!

    Your timing for this post couldn’t be better. Last night, Mr. Royale and I watched “Shut Up and Play the Hits,” the documentary about LCD Soundsystem’s last show at Madison Square Garden. The event alone was pretty sad, and listening to James Murphy talk about his decision to end the band got me a bit choked up. But I digress.

    I would agree with you that many Tom Waits songs are sad, or very sad (I always feel bad for the dog in “Frank’s Wild Years”), and that other songs, such as “Seasons in the Sun” are just plain old, maudlin and cheap attempts to make you to teary. (I would put “Wildfire” in that category, too.) Nonetheless, for me, a truly sad song is not one that elicits feelings of pathos or bathos, but one that hints are a greater “universal” sadness, or combines multiple feelings so that the sadness sort of slips in and is left with you, sort of like a yucky taste at the end of a seemingly tasty snack. To that end, I nominate two LCD Soundsystem songs for your consideration.

    1. “Someone Great” This song has always made me feel sad, despite it’s somewhat upbeat tempo. The lyrics reference a significant loss but it’s not clear who or what has gone. What ironically makes the song have some much impact are the apparent numb, surprised and resigned feelings of the narrator: it can be beautiful outside, and “the coffee isn’t even bitter,” as well as the realization that he can do nothing about his feelings and they will continue to keep coming (the repetition of “and it keeps coming, and it keeps coming till the day it stops).

    2. My other nomination is “Losing My Edge.” Outwardly, a pretty funny take on a musician who is starting to realize his lack of relevance, this song is a dark horse contender because of the connection to greater life significance. The narrator is complaining that “the kids are coming up from behind” while trying to still convince himself that he isl cool, after all “I was there” and names a number of great music events that it was not possible for him to have attended. As the song continues, it’s apparent that the guy is continuing to try to convince others as well as himself that he is meaningful, and to prop up his thin sense of self. His bragging, narcissistic comments are pathetic but also reflect the greater general confusion and angst that we all have felt at times when we question our place in this world. That is pretty darn sad.

    Thank you for humoring my rhapsodic and purple prose. Sad songs do that to folks.

  2. I really enjoyed that documentary even though I didn’t know a single song by them. I will have to give those songs a closer listen but kudos to you for picking a song that isn’t about death and can still be a contender.

  3. “Losing My Edge” is great…but I think sad might be a stretch. It is possibly the funniest song ever.

    I’d like to nominate ” ’til I Die” by the Beach Boys. Even without the backstory, it really gets across undistilled sadness. No story or concrete tragedy, just metaphorical despair.

    Oh, and it’s really great.

  4. ladymisskirroyale

    I’ve always been amused by “Losing My Edge,” but it was seeing it in the context of the James Murphy-feeling-confused-and-sad-during-and-after-his-last- show documentary that I realized that the song had a double/sad edge.

  5. BigSteve

    I say Townes Van Zandt’s Tecumseh Valley is the saddest song, and it’s made even more desolate by Townes’ matter of fact performance in this version recorded in a bar.

  6. misterioso

    I’ll submit Bob Dylan’s “If You See Her Say Hello” for consideration. “Either I’m too sensitive, or else I’m getting soft.”

  7. ‘Til I Die and Tecumseh Valley are great ones.

    I’ll thrown in Autumn Leaves, a jazz standard that has been covered a million times by pop artists from Sinatra to Rickie Lee Jones, but it’s always gets me when done well.

    PS A plug for Shannon — by Henry Gross, but I think that falls into the Seasons in the Sun category.

    Perhaps because of the high percentage of dog owners in Minnesota, radio stations played Shannon incessantly when I was about 7 years old.

  8. The saddest song…excluding yet another refrain from me as some Rhetorical Travis Bickle, unleashing his wrath on a half dozen call center people at 2 airlines? Mmm…I’m so prone to a spectrum of sadness that it’s hard to determine what exactly is sad vs what is mournful vs what is some other variant that any song is triggering that’s already in me. A song that really gets at one of my core triggers of sadness is Bob Dylan’s “I Don’t Believe You.” It’s not like I break down in tears every time I hear it, but it so perfectly captures feelings of abandonment and anger, which I can relate to.

    Now, speaking of sadness and sappiness and airlines, how about “I’m Leaving on a Jet Plane”? If only it had a verse about asking airline call center people dozens of dick-ish rhetorical questions meant to highlight their impotence in helping me rectify a technical problem I encountered during check-in.

  9. tonyola

    One of the saddest songs I can think of is Steppenwolf’s “Snowblind Friend”. Written by Hoyt Axton, the song describes the terminal slide of an addict. The music and the singing match the lyrics.

  10. misterioso

    Mod, I’d be interested in hearing more of your thoughts on “I Don’t Believe You.” I love the song and even though the words on the page indicate sadness, abandonment, and anger, the performances (giddy, in the original version on Another Side of BD; exhilarating, in the live 1966 version) tell another story, at least for me.

    But it sounds like now you need to listen to Paul Revere and the Raiders “The Great Airplane Strike.”

  11. trigmogigmo

    The Cure’s “To Wish Impossible Things” is musically beautiful and the lyrics seem to fit until the latter part which becomes simply and effectively expressed despair.

  12. BabaOLewie

    Some of you may not consider this Rock, but then again neither is Leaving on a Jet Plane (a song that reminds me instensely of my parent’s divorce when I was 5 and leaving NYC for Philadelphia and makes me sad in a very confused way, because planes are — or at least used to be — generally pretty fun).

    To me the saddest song is a song called “Maureen” by Sade. It’s about the death of a childhood friend. The saddest lyrics are

    Never going to see you again, Maureen
    And you’ll never meet my new friends.

    Pretty direct for me — cuts right to it. Plus her voice is always sad, even when she sings about Smooth Operators.

    Plus, on that score, any song by Billie Holiday, really doesn’t matter which one.

  13. machinery

    Big black car and Holocaust from Big Star’s Sister Lovers have always struck me as real deep, dark holes of songs.

    And X’s cover of Dancing with tears in my eyes takes on a real sadness for me given Exene’s sister’s recent death.

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