Nancy McCallion

Songs for Sinners

Ten Great Sad Songs

A couple of weeks ago I was talking to a club owner about adding some dates for the spring and we were discussing possible schemes to bring in more people. She informed me that her employees loved the band, and she had great respect for our musicianship, but one of her regulars complained, “Nancy does too many slow sad songs.” Aside from the fact that this isn’t true, (we do fast sad songs too,) I can’t understand not liking sad songs. Does hearing “Don’t Worry, Be Happy” make you stop worrying and be happy? I actually become more worried and very unhappy every time I hear that song.

Sad songs make me happy. Here is a list of some of my favorites. All these songs are slow, and therefore not the best choice for bar gigs, although you might be able to get away with one per set. Especially if the song is a waltz or “belt buckle polisher” as slow dances are referred to on the VFW circuit.

1. Ruby’s Arms – Tom Waits
A great sad song has a beautiful melody that can almost stand alone. Tom Waits is the voice of heartache in this one. The final line of the last verse kills me, “I’ll never kiss your lips again/or break your heart/as I say goodbye, I’ll say goodbye/say goodbye to Ruby’s arms.” Writing “I’ll never kiss your lips again” followed by “or break you heart” is terribly poignant; we know the singer’s heart is also breaking although he never actually says so.

2. Eleanor Rigby – Lennon and McCartney
This is one of the saddest of all The Beatles songs. Sad, tragic, but never maudlin. “She’s Leaving Home” is another and also Paul McCartney’s “For No One.”

3. Fairytale of New York – Shane MacGowan
You know a song that starts with “It was Christmas Eve babe, in the drunk tank” is going to be sad. But the refrain, “The boys from the NYPD choir were singing ‘Galway Bay,’ and the bells were ringing out for Christmas day” is genius. MacGowan takes us from the first Christmas of a young immigrant couple, through their self-destructive battles, and finally, the bitter end with the singer in the drunk tank, while throughout the narrative, the NYPD choir continues to sing a beloved song of their homeland.

4. Sam Stone – John Prine
“There’s a hole in Daddy’s arm where all the money goes, and Jesus Christ died for nothing I suppose.” These lines speak for themselves. If you don’t know this song, give it a listen, and have your hankie ready.

5. The Way it Goes – Gillian Welch This is a fine example of showing, not telling, just what your English teacher always told you to do and something we don’t get enough of in popular music.

6. I Think its Going to Rain Today – Randy Newman
This may be the most sarcastic sad song every written, a great combination of melody and irony.

7. Waltzing’s for Dreamers – Richard Thompson
Just putting a song in 3/4 time lends it poignancy, combine that with a beautiful melody and a loser in love and the melancholy tears start to flowing. Another sad and lovely Richard Thompson song is “Dimming of the Day.”

8. Sweet Old World – Lucinda Williams
Suicide is not an easy topic for a song, but Lucinda pulls it off, listing the things that make life worth living and asking “didn’t you think anyone loved you?”

9. I’m So Lonesome I Could Cry – Hank Williams
If your going to write about sad songs, you’ve got to yank a Hank. This song is a standard, a beautiful combination of melody and lyrics. There’s no pretention here: “I’ve never seen a night so long/when time goes crawling by/the moon just went behind the clouds/to hide his face and cry.”

So, I’ve come to my tenth song and I have a page of titles left that I’ve jotted down, and many more I’m sure to think of tomorrow. So I’ll end here with a song from my repertoire and save my ever expanding list of favorite sad songs for future posts. Please feel free to post your own favorites in the comments.

10. My Old Friend the Blues – Steve Earl
This seems a fitting song to end on. Embrace the sorrow; it’s one thing you can always count on in this sweet old world.


  1. Just an FYI, it’s Gillian Welch.

  2. I nominate “Old Tramp Steamer.” Talk about melancholy.

    • nancymccallion

      January 6, 2016 at 3:23 pm

      Thank you. That is a sad one. I used to choke up whenever I came to the line “I left my father, mother and brother for everything better and everything new.”

  3. Sad songs, huh. You site Tom Waits’ RUBY’S ARMS. One of my favorite songs of all time. Another one of his that’s always gets me is KENTUCKY AVENUE. Over a rather meandering melody he reminisces about childhood – gooseneck risers, sticking a tongue down a girl’s mouth, etc., but on the last verse, as the background swells and the melody coheres, he steals a hacksaw from his dad to cut the braces off his girlfriend’s legs – he swears he’ll take the spokes from her wheelchair and a magpie’s wing, tie them to her shoulders and her legs. Then they’ll fly together to New Orleans in the fall. Maudlin, perhaps, but heartfelt and incredibly effective none the less.

    Another one that tears me up just thinking about it is I’M HENRY THE EIGHTH, I AM. The bouncy feel of the tune belies an undercurrent so bleak one has to delve back to Euripides’ MEDEA to find a just comparison. The narrator, contemplating his mundane, frighteningly pointless, and most likely agoraphobic life, can go no farther than next door to find a mate. Once this is achieved, the revelation that he is not only her 8th husband but that the previous 7 had the exact same surname, leaves him barely able to function. Trapped in a cycle worthy of Dante’s downward spiraling inferno, he endlessly repeats his self-flagellating mantra “I’m Henry the 8th I am, Henry the 8th I am, I am” ad infinitum…Emphasizing his revelation of wasted, unending hell, he spews with bile and cynicism, “SECOND VERSE, SAME AS THE FIRST!!” Meanwhile, the unnamed fickle ingenue, proudly announces that she “Wouldn’t have a Willie or a Sam.” These names, carefully chosen, reverberate with a sense of impending doom and unbearable melancholy. “Willie” obviously refers to WILLIE LOMAN the hapless protagonist of Arthur Miller’s tragic masterpiece, DEATH OF A SALESMAN – A man who has become a footnote to his own life – burdened with a job creeping up on obsolescence, an embarrassment to his family, suicide rapidly becomes a more and more attractive way out.
    “SAM” more than likely refers to SAM THE LION, a central character in McMurtry’s THE LAST PICTURE SHOW. Sam’s demise triggers the final death knell to the nearly lifeless small Texas town that is the centerpiece of this tale of wasted youth and dashed hopes. Pathetic perhaps, but understandable why she wouldn’t have a “Willie or a Sam!”

    Even the band’s name – HERMAN’S HERMITS conjures up feelings of sadness and isolation. The band leader, HERMAN, representing the heartless God that oversees his flock of HERMITS – What is a more graphic reminder that we die alone than the image of the “hermit?” Are we not all “hermits” in the end? As bleak as this this song is, their follow up, MS BROWN YOU’VE GOT A LOVELY DAUGHTER was so overwhelming in it’s depiction of mendacity and despair, that three members of the band committed suicide soon after the recording was completed. ( The bassist, COLIN MORELY died of auto erotic asphicsiation, so I guess he really doesn’t count).

  4. Catherine zavala

    January 7, 2016 at 11:13 pm

    Alone again, naturally – Gilbert O’Sullivan

    This song has always been a tearjerker for me, ever since my mother died it’s more of drop-to-the-and-sob song.

    • Catherine zavala

      January 7, 2016 at 11:14 pm

      The missing word is floor

    • nancymccallion

      January 18, 2016 at 10:08 pm

      I love “Alone Again, Naturally.” I love the rhyme pattern, with the inside rhymes. It’s a very well crafted song although I tend to think of it as a guilty pleasure, just because it’s a bit overblown.

      “In an effort to make it clear to whoever what it’s like when you’re shattered
      left standing in the lurch at a church with people saying
      “my god that’s tough she stood him up no point in us remaining…”

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