The 50 Saddest Songs of All Time

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20. Laura Viers – “Sadako Folding Cranes”
When your topic is the atom bombing of Hiroshima, the resulting tune isn’t going to end up in your “happiest songs” list. This track off singer/songwriter Laura Veirs’ most recent 2013 album Warp and Weft is a tribute to Sadako Sasaki, a Japanese child who lived about a mile from the epicenter of the Hiroshima blast, and was 2 years old when the bomb fell. Despite being literally blown through a window by the blast, Sadako appeared to be relatively unharmed and lived a normal childhood until she developed leukemia at the age of 11 from the lingering radiation. Confined to a hospital and slowly dying, she was told the Japanese legend of the “1000 origami cranes,” whose creator would supposedly be granted a wish. In her dying days, Sadako therefore worked on folding her own 1,000 cranes, but passed away having only completed 644. The remaining cranes were finished by friends and family, and the poor young victim of WWII was ultimately buried with them. The whole story is recounted in much more detail in a work of historical children’s fiction by Eleanor Coerr, Sadako and the Thousand Paper CranesJim Vorel

19. Drive-By Truckers – “Little Bonnie”
Look, when your name is Bonnie, a song about a dead girl called “Little Bonnie” is going to make you sad. When your dad still calls you “Little Bonnie” sometimes even though you’re a few months shy of 27 and the song kicks off with the line “On the day that she was buried/Her Daddy stood out by the cemetery fence/Prayed to God for forgiveness/For surely all of this is punishment for my sins,” it’s pretty much tailor-made to make your heart ache. But you don’t have to be a Bonnie—little or big or in-between—to be moved by this Drive-By Truckers track. There are few things in life as tragic as dead kids, and sadly, “Little Bonnie never married, Little Bonnie never even made it four.”—Bonnie Stiernberg

18. Beck – “Lost Cause”
When Beck released Sea Change in 2002, gone were his freeform experimentations in the jigsaw jazz and get fresh flow. In its place was one of the most depressing-sounding—and artistically brilliant—albums in recent memory. Highlighted (lowlighted?) by the admonishing acoustic cut “Lost Cause,” a hallucinatory goodbye letter to an unknown lover, Beck’s repeated refrain of “I’m tired of fighting” sounds as eerily comforting today as it did over a decade ago.—Ryan J. Prado

17. Gary Jules – “Mad World”
This 1982 Tears For Fears song achieved another round of fame when Gary Jules and Michael Andrews covered it for the Donnie Darko soundtrack in 2001. Jules and Andrews traded the original pulsating synths for a stark, arpeggiated piano line and soft mellotron swells that arguable better emphasize the brooding lyrics of alienation. Within the narrative, “Mad World” builds a universe of nameless faces in common situations, from birthday parties to school classes. But in the chorus, Jules manages to laugh in spite of his dreams of death. It’s the ultimate mockery to compensate for (and attempt to comprehend) our irrevocable finality.—Hilary Saunders

16. Vern Gosdin – “Chiseled in Stone”
That molten caramel voice drenches an acoustic guitar. Another man-fighting-with-his-wife country ballad is deceptive as the chorus swells up “You don’t know sadness til you face life alone / You don’t know about lonely ’til it’s chiseled in stone…” Suddenly, sorrow’s permanence is concrete, pride is poison and Vern Gosdin bends notes and your heart. It’s 1989’s Country Music Association’s Song of the Year for good reason.—Holly Gleason

15. Johnny Cash – “Long Black Veil”
I was trying to keep this list to one song per artist and almost included Lefty Frizzell’s original version of the song, but Cash’s is just more potent. Written by Marijohn Wilkin and Danny Dill in 1959, the song tells the tale of a man wrongfully hanged for a murder because his alibi happens to be married to his best friend. Rather than betray his love and ruin a marriage, he carries the secret to his grave, leaving his lover in a state of constant mourning.—Josh Jackson

14. The Velvet Underground – “Pale Blue Eyes”
A hauntingly beautiful tale of unrequited love, “Pale Blue Eyes” is about recognizing you’re being used and allowing it to happen anyway. It’s one of the few songs that can make the phrase “best friend” feel as cutting as a four-letter word, as Lou Reed sings “It was good what we did yesterday, and I’d do it once again. The fact that you are married only proves you’re my best friend.” Anyone who has ever been friend-zoned can relate to the aching sadness oozing from this track.—Bonnie Stiernberg

13. Joy Division – “Love Will Tear Us Apart”
There’s no misery quite like seeing the ashes of what was once love’s burning fire. Ian Curtis captures that despair on Joy Division’s most recognizable song. A relationship full of resentment, as the bedroom has turned cold and all his failings have been exposed, is something to mourn, and everything about this song super-charges that mopey feeling. There’s nothing more empty than the space where love used to be. —Josh Jackson

12. Aretha Franklin – “Ain’t No Way”
Songs about unrequited love are inherently sad, but “Ain’t No Way” is one of those rare melancholy masterpieces that makes you want to nod knowingly in support and raise your hands in silent agreement while Aretha testifies. To say she sings her heart out on this song would be trite and also a gross understatement—she turns in a wailing vocal performance so good that she manages to overpower Cissy Houston’s otherworldly backup “ooooOOOOOOOOOO”s and make you forget where you are as the horns swell and her pleas to the man who won’t love her back grow more and more desperate. It’s sad, yes, but it’s also life-affirming that there are still people out there like Aretha loving this deeply—whether the feelings are reciprocated or not.—Bonnie Stiernberg

11. Harry Chapin – “Cat’s In The Cradle”
“Cat’s in the Cradle” is a song so sad that it’s become shorthand for the idea of sad, manipulative songs, to the point that it’s practically a punchline—you couldn’t help but laugh when it popped up so guilelessly in a Nissan commercial in this year’s Super Bowl, reinforcing the odd theme of “sad fatherhood” ads running that evening. It preys on the guilt of every career-dedicated parent—first you don’t have any time to spend with the kids because you’re always working, and then they grow up and don’t want to spend any time with YOU. “How did we drift apart?” the parent presumably asks, only to be told by the kid, “I learned it from watching YOU, Dad!” It’s a song that will put tears in the eyes of many parents, but in reality you could use practically any Harry Chapin song for this kind of list, as depressing stories were really the guy’s true medium. There’s the song about the band on the Titanic, playing as the ship sinks. Or the song from the perspective of a crooked cop trying to hide his kickback money from his young son to not lose his respect. Or the song about the evil small-town mayor who tricks his illegitimate son into hooking up with his half-sister. THESE ARE ALL REAL. Harry Chapin is not kind to the characters in his songs.—Jim Vorel

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