Musical Heartbreak: 12 Saddest Songs That Left Us in Tears

Unhappy woman listening to songs
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Music mends broken hearts, fixes torn friendships, and denotes painful, universal truths. To me, the saddest songs right now are “Orange Juice” by Noah Kahan, “listen before I go” by Billie Eilish, and “I Can’t Make You Love Me” by Bonnie Raitt. Music aficionados share their favorite morose tunes that always succeed in bringing tears to their eyes.

1. Oh My Darling Clementine — Freddy Quinn

Man crying
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Quinn croons about the horrific loss of his baby girl. “Oh my darling Clementine, you are lost and gone forever,” Quinn belts in front of a female chorus. According to the lyrics, Quinn’s character couldn’t swim, so when his daughter drowns in the sea, he can’t save her.

2. I Can’t Make You Love Me — Bonnie Raitt

Bonnie Raitt
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“I used to work in audio engineering and flew out for a conference in LA some years back. I got to sit in on lectures from some of the greatest producers and engineers in the industry. One of them was the producer of “I Can’t Make You Love Me.” When they recorded this song, almost all the engineers, producers, tape ops, and even runners were guys, and it was kind of a macho boys club. So she went in to do the vocal takes, a routine day. By the end of the first take, ten grown men were sobbing in the control room. Apparently, everyone was pretty much inconsolable, unable to catch their breath wailing. It was a long day,” a Raitt fan shares.

3. Between the Bars — Elliot Smith

Alcoholic man
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Elliot Smith knew how to utter the most painful lyrics in a lilting lullaby. “Between the Bars” centers around an alcoholic running from their past, abandoning their families, jobs, and priorities for a sweet sip of poison.

4. One More Light — Linkin Park

MADRID - JUN 22: Linkin Park (music band) perform in concert at Download (heavy metal music festival) on June 22, 2017 in Madrid, Spain
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“One More Light” opens with a haunting percussive reverb before Chester Bennington’s smooth vocals enter into the tune. “Who cares when someone’s time runs out, if a moment is all we are, or quicker?” Bennington sang each note with a poignant sadness. “Who cares if one more light goes out in a sky of a million stars?”

“We do, Chester. We shall forever do,” a fan says.

5. Casimir Pulaski Day — Sufjan Stevens

BILBAO, SPAIN - NOV 01: The National with Sufjan Stevens (band) live music show at Bime Festival on November 01, 2014 in Bilbao, Spain.
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Sufjan Stevens nails delivering sweet-sounding notes over light instrumentals, yet he unleashes horrifying and depressing lyrical content. In “Casimir Pulaski Day,” Stevens details a relationship with a woman who has “cancer of the bone.” Through painstaking lyrics, we delve through the narrator’s relationship, ending in her death, “In the morning, when you finally go, and the nurse runs in with her head hung low.”

6. Accidentally Like a Martyr — Warren Zevon

Sad man listening to music
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Zevon yearns for the return of his lost love, acknowledging sometimes the worst loss is one where the person relives happy memories. “The phone don’t ring, and the sun refused to shine. Never thought I’d have to pay so dearly for what was already mine,” he laments into the void.

7. I Will Follow You Into the Dark — Death Cab for Cutie

Girl crying listening to song
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Rock bands love tackling difficult material through wholesome lyrics. “This song actually came on our random playlist the morning of the day my wife died. We knew she was dying, but we didn’t know it was going to be that day. We actually had a nice little smile about it. Strange but true,” a music lover commented.

8. What Sarah Said — Death Cab for Cutie

Man crying
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This six-minute song begins with a beautiful piano intro, warming up the listeners for a melancholy story. “What Sarah Said” revolves around a narrator in the ICU, watching someone he loves give more and more of themselves away to death’s grip. Halfway through the song, the narrator pipes, “But I’m thinking of what Sarah said, ‘Love is watching someone die.'”

This admittance gives way to an upbeat marimba and a wondrous chorus rippling through the song’s final moments, “So who’s gonna watch you die?”

9. The Night We Met — Lord Huron Feat. Phoebe Bridgers

Napa, CA/USA: 5/26/19: Lord Huron performs at BottleRock. Their debut album, Lonesome Dreams, was released in 2012. In 2018 they released their third album Vide Noir.
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I can’t listen to this song without imagining Clay Jenkins in Thirteen Reasons Why sobbing over the loss of his classmate and crush, Hannah Baker. Lord Huron and Bridgers’ voices complement each other so well they rock your core. The song focuses on a lost love who can’t move on based on the adoration shared between two parties and the fateful night they stumbled into each other. “I had all and then most of you, some, and now none of you.”

10. listen before i go — Billie Eilish

Sad teenage girl listening to music and crying
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Billie Eilish’s mother asked her if she thought releasing this song was a good idea based on the subject matter. A singular piano chord launches the last lamentation of a teenage girl who decides to end her life. “If you need me, wanna see me, better hurry, ’cause I’m leaving soon. Sorry, can’t save me now.” This song hits home in a world with a high level of mental health struggles.

11. The 30th — Billie Eilish

16-18 augustus 2019. Lowlands Festival, The Netherlands. Concert of Billie Eilish
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I would argue this song is Eilish’s saddest. “The 30th” commences with a downcast fingerpicked intro. “Sometimes you look the same, just like you did before the accident,” Eilish voices. Eilish introduces a scenario where her close friend almost dies in a terrible car wreck and emotes a spine-tingling bridge with, “What if it happened to you on a different day? On a bridge where there wasn’t a rail in the way? Or a neighborhood street where the little kids play? Or the Angeles Crest in the snow or the rain? What if you weren’t alone? There were kids in the car. What if you were remote? No one knows where you are. If you changed anything, would you not have survived? You’re alive, you’re alive, you’re alive.”

12. Ronan — Taylor Swift

Taylor Swift
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“Truly. I don’t think it’s a well-known song, but I was looking for this answer. Immediate sobbing. I have to skip it. If you’re a parent and can listen to that without crying, I would be surprised,” a user states. “Listening to this song is like cutting onions. I fall to pieces every time,” another person states.


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Written by Gabrielle Reeder

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