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Love, Death, and Tragedy: 10 Sad Love Songs That Will Break Your Heart

Kyson is a long time music-lover, play-list maker, and foot-tapper.

Tragic love songs are touching and poignant—here are the top 10.

Tragic love songs are touching and poignant—here are the top 10.

What Are the Best Sad Love Songs?

Why do we love tragic stories? We know how Pearl Harbor and Romeo & Juliet each end, but we flock to these stories regardless.

A well-written tragic love ballad can tear your heart to pieces, but for some reason, we listen to them anyway. Here are ten awfully sad but poignant songs about love, death, and tragedy.

Have tissues handy.

The Top 10 Sad, Tragic Love Songs

  1. "Long Black Veil" by Johnny Cash
  2. "O Valencia" by The Decembrists
  3. "The Girl I Loved in Tennessee"
  4. "Casimir Pulaski Day" by Sufjan Stevens
  5. "Swallowed in the Sea" by Coldplay
  6. "Murder in the City" by The Avett Brothers
  7. "We Remain as Two" by Page France
  8. "Samson" by Regina Spektor
  9. Album: The Hazards of Love by The Decembrists
  10. "I Will Follow You Into the Dark" by Death Cab for Cutie

1. “Long Black Veil” by Johnny Cash

Cash, an expert at dark ballads writes this story of a man falsely accused of murder who faces death rather than to give up that he was having an affair with his best friend’s wife.

The judge said son, what is your alibi

If you were somewhere else, then you won't have to die

I spoke not a word, though it meant my life

I'd been in the arms of my best friends wife

Check out this excellent cover by ‘gothic folk’ genius Iron & Wine for the 2012 We Walk the Line: A Celebration of the Music of Johnny Cash.

2. “O Valencia” by The Decembrists

This morbid Romeo & Juliet-inspired indie-rock tune is one of The Decembrist’s most popular songs, and for good reason.

Well, how soon we were betrayed

Your sister gave us away

And your father came all unhinged

3. “The Girl I Loved in Sunny Tennessee”

This tear-jerking country & western classic. I recommend the new life given to this tune in the cover independent folk-genius Sam Newcomer.

As I whispered, mother dear, where is Mary, she's not here

All the world seemed lost and sadness came to me

For she pointed to a spot in the churchyard's little lot

Where my sweetheart sleeps in sunny Tennessee

4. “Casimir Pulaski Day” by Sufjan Stevens

The story of a teenage girl who dies from cancer by banjo-strumming, composer, Sufjan Stevens on his most successful record: Illinoise! which forms part of his now abandoned project of writing an album for every state in America.

All the glory that the Lord has made

And the complications you could do without

When I kissed you on the mouth

5. “Swallowed in the Sea” by Coldplay

This Coldplay song has been open to a variety of interpretations. It can easily be read as mourning the death of a lover – with the sea as a common ancient reference to a place of evil and death, and other images in the song that imply the other person existing in an afterlife:

Oh the streets you're walking on

A thousand houses long

Well that's where I belong

And you belong with me

Not swallowed in the sea

6. “Murder in the City” by the Avett Brothers

Remember there was never a love worth sharing

Like the love that let us share our name.

Those are words for a wedding invitation.

7. “We Remain as Two” by Page France

This sad meditation on a deceased lover is by the obscure indie-folk band Page France whose first album, ‘Come, I’m a Lion!’

And if they give to you your wings

will you think to give to me your arms?

8. “Samson” by Regina Spektor

The hit by Regina Spektor which seems to be about a hypothetical lover who the biblical Samson rejects for Delilah who betrays him.

Samson went back to bed

Not much hair left on his head

Ate a slice of wonder bread and

Went right back to bed

And the history books forgot about us

And the Bible didn't mention us

Not even once

9. Album: The Hazards of Love by the Decembrists

The Decembrists have a long repertoire of tragic ballads. Their fifth studio album, The Hazards of Love, forms an album-length epic in the form of a gothic/classical literature fusion tells the fantastical story of young prince under a spell by his witch-mother and his quest to undermine her sadistic schemes to take his beloved away from him. The final track “The Hazards Of Love Part 4” is front-man Colin Meloy at his lyrical best, exuding his Victorian-level poetic sensibilities.

With this long last rush of air

We'll speak our vows in starry whisper

And when the waves came crashing down

He closed his eyes and softly kissed her

These hazards of love never more will trouble us

And these hazards of love never more will trouble us

10. "I Will Follow You Into the Dark" by Death Cab for Cutie

One of Death Cab for Cutie's biggest mainstream hits.

Love of mine some day you will die

But I'll be close behind

I'll follow you into the dark

No blinding light or tunnels to gates of white

Just our hands clasped so tight

Bonus: “Hallelujah” by Jeff Buckley

While not explicitly about death, this universally acclaimed song of lost love stretches the bonds of a typical ‘break-up’ song with its evocation of Biblical tragic love stories and the poignant depths of despair and pain it explores.

Well your faith was strong but you needed proof

You saw her bathing on the roof

Her beauty and the moonlight overthrew ya

She tied you to her kitchen chair

And she broke your throne and she cut your hair

And from your lips she drew the Hallelujah

See my article on the fascinating history of this song.


Steph Mineart on January 12, 2015:

The Highwayman - Lorenna McKennitt

I'm stretched on your grave - Irish folk tune, notably sung by Sinead O'Connor

Annabelle Lee - Sarah Jarosz - gorgeous arrangment of Poe's poem

vanessa on August 26, 2014:

Hey I've lost my love in a car accident can anyone help me find a soft song that may comfort me!?

newenglandsun on February 13, 2013:

You are missing "It's All Coming Back to Me Now" by Celine Dion. A song about a lover who died in a motorcycle accident but now the memories of this loved one are coming back to haunt the singer.