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Poor Poor Pitiful Me: A Reasonable Guide to Horribly Depressing Songs

As a native Chicagoan who grew up listening to men in black walking the line and grizzled bluesmen wearing their hearts on their throats, I have a pretty high tolerance for moving music that some might consider unpleasant. But even I have my limits. Following up on my Joy Division post, I’ll descend even further into the abyss by listing a few of the most depressing songs that have kidnapped my imagination. The title pays homage to a Lester Bangs essay, A Reasonable Guide to Horrible Noise, and to Warren Zevon’s boo-hoo ode to boo-hoo singer-songwriters, which improbably got Linda Ronstadt to record a Top 40 hit about tying her head to the railroad tracks. Woe is me!

• Samuel Barber, “Adagio for Strings” (According to Alex Ross, “whenever the American dream suffers a catastrophic setback, Barber’s Adagio plays on the radio.”)
• The Who, “Pictures of Lily” (Boy sees girl of his dreams and discovers she’s been dead for four decades.)
• Smokey Robinson and the Miracles, “Tears of a Clown” (When clowns aren’t creepy, they’re liars, or worse, opera fans.)
• Richard Thompson, “End of the Rainbow” (The author of ditties like “The Wall of Death” sings to a baby, claiming there’s nothing at the end of the rainbow. Thanks, Dad.)
• Nina Simone, “Little Girl Blue” (Bored, sad girl counts the raindrops and discovers evaporation.)
• Marty Robbins, “Streets of Laredo” (The singing gunslinger gets shot to death in “El Paso,” but that’s mild compared to this cowboy variation on the ancient “Unfortunate Rake” story.)
• Billie Holiday, “Gloomy Sunday” (The darkest version I’ve heard of the Hungarian Suicide Song. The composer later committed suicide.)
• Louvin Brothers, “Knoxville Girl” (The most violent song on the cherub-voiced death-gospel duo’s aptly named Tragic Songs of Life, reworking the English “Wexford Girl” murder ballad.)
• Big Star, “Holocaust” (Power pop drained of any power, words drained of any meaning, Beach Boys melodies sinking into quicksand.)
• Hüsker Dü, “Too Far Down”/ “Hardly Getting Over It” (The titans of melodic noise at their greyest, not seeing even a little light.)
• The Antlers, “Bear” (Heartbreaking ode to premature senility and the animal inside.)
• Etta James, “I’d Rather Go Blind” (Passive-agressive romantic obsession turns the lights out and entertains us.)
• Carter Family, “Engine 143” (Lots of songs are metaphorical train wrecks. This one’s the real deal.)
• Graham Parker, “You Can’t Be Too Strong” (“The doctor gets nervous completing the service, he’s all rubber gloves and no head.”)
• Pernice Brothers, “Chicken Wire” (Garage clutter, exhaust fumes, and no redeeming sentiments.)
• George Jones, “He Stopped Loving Her Today” (Why? Because he’s dead, that’s why.)

That playlist could keep you in therapy for years. But none of them outdo the real King of Pain, Skip James. Blues was never bluer. On “Devil Got My Woman,” Skip out-depresses the whole field by declaring that he’d rather be the devil.

Skip James, “Devil Got My Woman”

Big Star, “Holocaust”

Nina Simone, “Little Girl Blue”

From → Playlists

  1. rinchen permalink

    I like your nomination of Skip James, whose voice is so angelic that when sings he’d rather be the devil, it doesn’t sound scary, it sounds beautiful.

    As for my own choices of favorite depressed/depressing songs, I would include:
    Beatles’ “I’m so tired”/”Yer blues”
    Captain Beefheart’s “Making love to a vampire w/ a monkey on my knee”
    (“oh fuck that thing/fuck that poem/eyes crawled out with maggots/ white cloth bone”)
    Sun Ra “Nuclear War” (tho’ this song is actually grimly funny, too : “if they push that button/your ass’s got to go”)

    My least favorite would have to be Joy Division’s “Love will tear us apart”:
    dyspeptic synth & Ian Curtis sounding like he’s on quaaludes….groan.

  2. Roger permalink

    Great selections! I’d also add Lennon’s solo primal screams on “Mother.” As to the Captain, I’d run with “Dachau Blues” and leave whatever happened with the vampire and the monkey as a desert secret.

    I’ve struggled with gloom enough to find Ian Curtis moving, but he’s not for everyone. It’s true he was often heavily medicated (mainly due to worsening epilepsy).

  3. My sentimental-to-the-point-of-maudlin nomination is Harry Chapin’s 1974 war horse “Cat’s in the Cradle.” I know it’s a corny cliche’, but it’s a song that’s always put a genuine lump in my throat. As a child it affected me because I loved my dad so much, but his job with the railroad took him away for days at a time. He’s always made up for it by spending QT with us when he was home, but I still hated it every time he left. Now, as a father, I struggle from the other end – working hard, running to stay in place, trying to find time to spend something more than a few morning and evening minutes with my boy, scared to death he’ll grow up and move out and I won’t have milked every possible moment from the relationship. In the song, the dad blows it on that count, and it’s too late to get back the moments.'s_in_the_Cradle

    Another one that hits me hard is Leadbelly’s “In the Pines,” about a woman forced to wander the earth, sleeping in the forest outside of town on account of some real or imaginary wrongdoing, and whose husband’s head was apparently vaporized by a train. Gives me chills every time.

  4. Great list. Leonard Cohen of course has countless depressing songs. I’ll nominate Famous Blue Raincoat and Dress Rehearsal Rag. The latter starts off: “I stepped into an avalanche, it covered up my soul.” An Irish jig it is not.

  5. benoit baald permalink

    Speaking of ‘cat’s in the cradle’, here’s my morning bowl of father-son forlorned:

    Dream Letter (Tim Buckley)

    Lady time, fly away
    I’ve been thinking ’bout my yesterday

    Oh, please listen, darlin’, to my empty prayers
    Sleep inside my dreams tonight
    All I need to know tonight are you and my child

    Oh, is he a soldier or is he a dreamer?
    Is he mama’s little man?
    Does he help you when he can?
    Or does he ask about me?

    Oh, just like a soldier boy
    I’ve been out fighting wars
    That the world never knows about
    Oh, but I never win them loud
    There’s no crowds around me

    Oh, when I get to thinkin’
    ‘Bout the old days
    When love was here to stay
    I wonder if we’d ever tried

    Oh, what I’d give to hold him

    Dream Brother (Jeff Buckley)

    There is a child sleeping near his twin
    The pictures go wild in a rush of wind
    That dark angel he is shuffling in
    Watching over them with his black feather wings unfurled

    The love you lost with her skin so fair
    Is free with the wind in her butterscotch hair
    Her green eyes blew goodbyes
    With her head in her hands
    And your kiss on the lips of another
    Dream brother with your tears scattered round the world

    Don’t be like the one who made me so old
    Don’t be like the one who left behind his name
    ‘Cause they’re waiting for you like I waited for mine
    And nobody ever came

    I feel afraid and I call your name
    I love your voice and your dance insane
    I hear your words and I know your pain
    With your head in your hands and her kiss on the lips of another
    Your eyes to the ground and the world spinning round forever
    Asleep in the sand with the ocean washing over

  6. John Wright permalink

    I enjoyed the input on the slit-your-wrist tunes. I tend towards alt-country, and no that doesn’t mean “country.” I know labels are stupid but here are just three that immediately leap to mind.

    Gillian Welch – “Revelator”
    such a beautiful voice encased in a narcotic haze, think the Cowboy Junkies, but Cowgirl and “junkier.” At a tempo that is slower than molasses in January ( oh, I guess it’s now February ). Beautiful, torture.
    WARNING: do not listen to this song if you are feeling suicidal, yea, it’s that depressing

    The Gourds – ” Our Patriarch”
    mournful and beautiful, subtle chord changes, and the line about being buried in a coffin built by his own hands, Whoa!

    Now all around this border town

    The lads and lassies gather round

    All that is heard a mournin’ sound

    The salty tears a runnin’ down

    Our patriarch with greasy hands

    He held the golden cages key

    For twenty years he sailed the seas

    With a trumpet on his knees

    He drank the wine of ancient tung’s

    And with his hands began to build

    A tower for the bells we rung

    A temple for the whippoorwill

    Now all around this border town

    The lads and lassies gather round

    All that is heard a mournin’ sound

    The salty tears a runnin’ down

    With eyes of blue and jacket too

    In trousers red and beard of grey

    A casket built of his own hand

    Our patriarch has died today

    and truly harrowing has got to be Son Volt,
    “Cocaine and Ashes”
    the horrors of drug addiction, supposedly a nod ( get it ) to Keith Richards but I think that
    Jay Farrar knows his way around the pharmacy, too.

    I’ve had strychnine, I thought I was dead
    I snorted my father and I’m still alive
    I did it because that’s how it is done
    I’m the same as everyone, just kinda lucky

    Body and soul, cocaine and ashes
    We’ll get to that place in time
    Just tears and blow on my mind

    It’s no to way of life but I’ve tried everything once
    I have no pretensions of immortality
    But I’ve been told I had 6 months to live
    But I’ve outlasted them all

    Body and soul, cocaine and ashes
    We’ll get to that place in time
    Just tears and blow on my mind

    Senses and spirit, mourning and misery
    Addiction is something I should know something about
    Whatever gets done I know that I’ll be blamed
    But they say the king is the man who can

    “I’ve had strychnine, I thought I was dead”
    Really? go figure!

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