Ten Sublimely Sad Songs

I'm feeling much better today... thanks for all the kind comments, and I apologize for the shameless pandering (sham-pan, as Mattthew and I call it).

I was thinking this morning that one of the redeemable things about feeling down is listening to sad songs. There are many kinds of sad, of course, and sometimes listening to sad music is the last thing you want. But I find that listening to sad songs when I'm down can have an opposite effect -- sometimes it just feels good, like pressing on a bruise. It hurts, but in a proud sort of way.

So, in that spirit (and because i LOVE making lists), I decided to put together a list of ten of my favorite sad songs. Of course this list could be pages long, and I'll probably think of five better ones tomorrow, but I thought this might be a good starting point for some discussion.

Without further ado, ten sublimely sad songs.

1. Don't You See That Train? - The Delmore Brothers

My friend Greg put this on a mix CD for me several years go, and I've put it on several since then. The idea of a train is sad enough -- the moan of the whistle as the train slowly (not even mercifully quickly!) pulls away with someone you love. The concept, coupled with the perfect harmonies of these two real-life brothers, makes the song nearly too much to bear.

"Don't you see that train, dee-dee-dee / See that train, hey hey / She's leavin', she's leavin' on that train / And I'll never see my sweetheart again."

2. So Lonesome I Could Cry - Hank Williams

I could have simply spun a wheel to pick a Hank Williams song -- they're all sad. My friend Toby accurately described his voice as "like the wailing wall." And the accompanying guitar always sounds both drawn out and ploddingly on-rhythm, as if Hank is willing himself, through song, to keep going.

"The silence of a falling star / Lights up a purple sky. / And as I wonder where you are / I'm so lonesome I could cry."

3. Long Black Veil - Johnny Cash

I'll be the first to admit that I'm a sucker for the narrative song, particularly if it involves death. Although Johnny didn't write this one, his rendition has a particular poignancy because of his relationship with June Carter. The (dead) narrator in the song hangs for a crime he didn't commit because his only alibi -- "I'd been in the arms of my best friend's wife" -- would destroy the two people he loves the most. He describes how she visits him "in a long black veil," both of them keeping their secret beyond the grave.

Sad yet?

4. You Will Miss Me When I Burn - Palace Brothers

From one of the saddest albums of all time, Days in the Wake, this song is so quiet, yet so packed with Biblical-proportion vengeance. I never realized the extent of its wrathful goodness until years ago when a friend listened to it continually during a particularly bad breakup. Consider the mere mention of wolves in the following:

"There is absence, there is lack / there are wolves here, abound / You will miss me when I turn around."

I'm not sure about this, but I would swear Mr. Oldham is willing someone to be torn apart by wolves.

5. Out in the Streets - The Shangri-Las

Lesser known than the oldies radio staple, “Leader of the Pack,” the Shangri-La’s “Out in the Streets” is another example of the subgenre of Bad Boy Songs particularly popular in the late 50s and early 60s. But instead of the “I love him, but he’s so bad,” or “I love him because he’s so bad” themes, “Out in the Streets” adds yet another, more nuanced twist: “I love him because he’s so bad, and that’s why I have to let him go.”

This song even starts sad, with a chilling drawn-out “ooooooh,” followed by a pulsing bass line lurking under the vocals that confide, “He don’t hang around with the gang no more. / He don’t do the wild things that he did before.” Instead of celebrating a conquest, though, she knows that his heart is "out in the streets."

I think I must be attracted to acts of sacrifice in my expressions of sadness (see "The Long Black Veil" above). That this girl will let this guy go because she doesn't want him to change just breaks my heart every time.

6. Which Will - Nick Drake

In this song, the narrator is asking someone he loves to make a classic choice -- him or me. But he seems to know all along that the person isn't going to pick him: "Which will you dance for / Which makes you shine? / Which will you choose now / if you won't choose mine?"

My friend Joni who first introduced me to Nick Drake handed me the CD with a sticky note attached that said, "By the way - he says 'tell me now,' not 'I don't know.'" Until I listened to the song, I didn't know what she meant, but at the end of each verse, he quietly insists, "Tell me now / which will you love the best?"

7. You Could Make a Killing - Aimee Mann

Aimee Mann is a slight guilty pleasure for me. I know, I know... some of her songs are overproduced, and she tends to be a little precious and overly clever with her love of a convoluted grammatical construction. But so can I! And I return time and time to this song when I'm feeling low, despite a) its inclusion on the Cruel Intentions soundtrack, and b) her own admission that she wrote the song about one of the whingey Oasis brothers.

Still, this song really captures what it's like to know something is so obviously shallow and bad for you and STILL WANT IT.

"I wish I was both young and stupid / Then I too could have the fun that you did / Till it was time to pony up what you bid / So you could make a killing."

8. Crazy Love, Vol. II - Paul Simon

The whole Graceland album could go on this list -- what part of divorce isn't sad? Unlike some of the other songs on the album (and on this list), however, this song doesn't really sound sad at all. It's got a lilting little melody with a lacy layer of steel guitar over it. Ah, but the lyrics.

The song describes "Fat Charlie the Archangel" who is going through a painful divorce. He strikes me as a man whose life has just been happening to him for years when he finds out everything he's put stock in -- his marriage -- has been a sham.

"She says she knows about jokes / This time the joke is on me. / Well, I have no opinion about that / And I have no opinion about me.

Somebody could walk into this room / And say your life is on fire. / It's all over the evening news / All about the fire in your life / On the evening news."

8. Ever Fallen in Love? - The Buzzcocks

"Ever fallen in love with someone you shouldn't have fallen in love with?"

But of course you have.

This song is fresh in my mind because we heard Lianne Smith sing a great cover of it at Tonic last Sunday night. Her voice is the perfect combination of sweet and salty to pull off a sad song, even a punk-rock sad song. (Thanks, Lianne!)

9. Don't Explain - Billie Holiday

Again, sacrifice as a cause of sadness. I first heard of this song years ago in the Saul Bellow novel Herzog, where the main character makes one of his girlfriends listen to it so she'll learn not to take the relationship too seriously. After I heard the song, I realized just how cruel an act that was. Later I also learned that "Don't Explain" was co-written by Billie and Arthur Herzog.

In one of the saddest songs I've ever heard, Billie urges her man not to explain where he's been, even though it's clear that she knows.

"Quiet, don't explain / What is there to gain / Skip that lipstick / Don't explain"

Billie could sing bubblegum jingles and forests would burn.

10. Our Town - Iris DeMent

This song is about a death of a town, not of a clown (which we would drink to, because it would be funny. And, ok, maybe a little sad). You can hear the mourning in Iris' voice, and you know that part of her is dying with the town, but she has to get out. Reminds me of the line from David Berman's "Tennessee" that says, "You know Louisville is death / We've got to up and move / Because the dead do not improve."

Please write in comments with your favorite sad songs. Sad days always come back 'round, and next time we'll be prepared.