The 100 Saddest Songs Ever Made (#50–26)
50. “Trouble”- Coldplay
It’s hard to imagine, but once upon a time Coldplay were not pop superstars, hanging out with Rhianna on weekends and preforming at the Super Bowl. Once they were very polite British college students, reflecting on lost love while walking through a snowy campus. Despite “Yellow,” Parachutes is still Coldplay’s saddest album, mostly thanks to “Trouble.” Chris Martin isn’t singing really, he’s mewling, a teardrop in every note. The instrumentation feels dusty and barebones as Martin cries out his apologies. “I never meant to cause you trouble/I never meant to do you harm.” He sounds like an ashamed little kid, unsure of what he did wrong, but so sorry for whatever it was.
49. “The Con”- Tegan and Sara
“Nobody likes to but I really like to cry.” No Tegan and Sara, if we didn’t like to cry we wouldn’t be listening to “The Con” on repeat.
48. “Brothers on a Hotel Bed”- Death Cab for Cutie
Ben Gibbard is the master of rain-soaked Seattle sadness. The music of both The Postal Service and Death Cab for Cutie always seemed to be set in a blustery evening on the coast as a storm rolls in. “Brothers on a Hotel Bed” is, for me, the best example of this sort of songwriting. The clear-eyed piano sounds like a rainy day and the drums mimic the slow movement of cars below apartments, shops and hospitals. This is the backdrop Gibbard uses to tell the tale of an elderly couple, realizing that the spark in their relationship died long ago. “He lives inside someone he does not recognize when he catches his reflection on accident,” Gibbard sings. To add to the hurt, the couple stays together, because they still love each other, but it’s all become completely, painfully, platonic rather than the whirlwind romance it once was.
47. “Waiting ‘Round to Die”- Townes Van Zandt
Gambling, drug addiction, liver failure, jail time, domestic abuse, absent parents, “Waiting ‘Round to Die” hits every check mark on the sad country lyric ballot. Though it can be argued that Townes Van Zandt perfected that checklist. This sordid story ends with the protagonist high on clonidine and accepting that all his life he was just killing time.
46. “Motion Lines”- Busdriver
Busdriver’s amazing Perfect Hair was nearly genreless. Sure he rapped, but there were snippets of spoken word, rock n’ roll and glitch all fused together. “Motion Lines” was where he got his jazz man on and he decided to go for In the Wee Small Hours mode. Over a crying, click-clacking beat, Driver overanalyzes a confusing relationship where no one’s really sure what they want. “I’m impossible to love/Can I keep an open mind?” The short answer is no. The long answer is that Driver’s romantic pleas and self-destruction might be the end for both of them. Over a haunting chorus floating in the background, Drive admits “You look like my next wife” and, brutally, that “My love feels like a cervix tear.”
45. “Sad 2”- Frankie Cosmos
The dog dies at the end. That adorable little pupper on the cover, his name was JoJo and Frankie Cosmos made a whole album about how amazing he was. And how much she misses him. She recounts JoJo’s last few days over shimmering marimba. She closes with the sentiment that everyone has when a pet leaves: “I wish that I could kiss his paws.”
44. “I’m So Tired”- Fugazi
Between Minor Threat and Fugazi, Ian MacKaye had to run out of energy at some point. Eventually he did and made the uncharacteristically beautiful and somber “I’m So Tired.” A piano ballad stuffed between post-hardcore screams, “I’m So Tired” seems to have jumped out of a 1930s song book. “I’m so tired, sheep are counting me,” MacKaye sings, sounding absolutely defeated as the piano limps alongside him.
43. “Flirted with You All My Life”- Vic Chesnutt
Vic Chesnutt was left mostly paralyzed from the neck down after a car crash at 18. He found he could still play guitar, but only using simple chords. He attempted suicide multiple times after the crash, before passing away at 45 from an overdose of muscle relaxants. The “You” in the title is Death. “Decimate those dear to me/You tease me with your sweet relief,” he sighs in his cracked, failing voice. I don’t know if I can add more.
42. “Asleep”- The Smiths
Oddly enough, The Smiths were one of the easiest bands to pick one song from. It’s not that they don’t have dozens of sad songs, it’s just that “Asleep” is so much more depressing than everything else. There’s a deep lethargy to “Asleep,” like Morrissey is going to pass out at any moment. Howling winds accompany the funeral piano as Morrissey contemplates suicide. “There is a better world/Well, there must be,” he sings before the winds swallow him whole.
41. “Sweetheart, What Have You Done to Us”- Keaton Henson
Keaton Henson could sing the phonebook and it would still be tearjerking. He’s just got this bird-like, brittle voice that always sounds like its going to give out. So when he does sing lyrics that equal his somber voice it’s not a question of “if tears” but “when tears.” “And if all you wanted was songs for you/Well here goes, after all that you’ve put me through…/And don’t call me lover, it’s not enough.” He’s channeling some bitter version of Jeff Buckley here before the song explodes in horns and Henson is left alone.
40. “Ambre”- Nils Frahm
I originally had the full “Unter-Tristana-Ambre” suite from Nils Frahm’s brilliant live album Spaces — and I couldn’t find a full clip on Youtube. But the series’ emotional centerpiece “Ambre” is fully available to cry to. With Chopin-like sensibilities, Frahm and his piano weave a wintery world. Only occasional chiming notes from above join. This is post-Christmas music, melodies for long walks in the snow without the promise of presents or fireplaces after.
39. “Something in the Way”- Nirvana
Nirvana have a relatively small catalogue of songs so that should make it easier to pick a song right? Wrong. What Nirvana lacks in quantity they make up in tears. I ended up picking the bummerest of all bummer closing tracks, “Something in the Way.” Kurt Cobain’s hummed, doomed vocals pared with violin did wonders on In Utero and MTV Unplugged but they did it first and best on “Something in the Way.” Written about Cobain’s time living under a bridge after being kicked out of the house by his family, the song speaks to utter desperation giving way to resignation.
38. “Benaz”- Riz MC
Riz MC’s ENGLISTAN, was about “multiculturalism not as a buzzword, but as lived experience.” It’s a vibrant, and dangerous picture of London Riz paints, but he never does it as brutally as he does on “Benaz.” He steps away from first person raps to narration about an Iraqui-British woman named Banaz Mahmod. Over 11 minutes, Riz follows Mahmod’s home life, filled with suppression and domestic abuse. Forced into an arranged marriage by her father, she finds escape in British nightlife and falls in love with a man her family doesn’t approve of. Things turn horrific quickly. I can’t give away the rest, because Riz’s storytelling is too powerful for me to undercut, but I will say that “Benaz” is a spoken-word masterpiece of the 21st century.
37. “Varúð”- Sigur Rós
In direct opposition to the narrative heavy “Benaz,” “Varúð” is sung in Icelandic, and I’ve never found a great translation. It doesn’t matter one bit. Sigur Rós’ grand symphonic tendencies are on full display, with an orchestra worth of strings rising and falling with the chorus, spearheaded by the angelic voice of Jónsi. The watery piano line repeats again and again beneath it all, before the song slowly builds into a maelstrom of choirs, strings, drums and a screaming guitar that seems on the edge of being torn in two. “Varúð” doesn’t care about the small details, it is content to be awashed in a great sadness.
36. “Matthew 25:21”- The Mountain Goats
Well there had to be one Mountain Goats song right? And I had to pick “Matthew 25:21” because it starts with a loved one in hospice and the protagonist hoping he doesn’t take anyone else with him when he crashes his 18 wheeler. And it only gets worse from there.
35. “Obstacle 1”- Interpol
Sharp dressed sad-sacks Interpol took the depressed world by storm with Turn On the Bright Lights. It was a direct call back to the somber post-punk of the 70s and 80s, but with modern neurosis. “Obstacle 1” still stands as their finest moment, with an impeccablely melodic bass and the most emotional drum solo of all time. Paul Banks’ croak details a lover noticing that everything’s falling down around them. “She can read, she’s bad/Oh, she’s bad,” he cries, hoping he can hide everything before she realizes how broken they are. Add that slicing and iconic riff to Banks launching into “She puts the weights into my little heart” and you’ve got a New York City breakdown of biblical proportions.
34. “Pontiac”- Lyle Lovett
Lyle Lovett’s detail loving short stories are usually humorous, self-effacing romps. He has plenty of sad songs, like the domestic abuse of “Black and Blue” or the cowboy blues of “Which Way Does that Old Pony Run,” but he has one truly devastating track up his sleeve, “Pontiac.” He becomes a WWII veteran in small town Texas, where the neighbors see a “nice old man.” Nothing tells his friends or family that he’s gripped by PTSD, “I killed twenty German boys/With my own bare hands.” His wife offers no comfort, our protagonist only joined by a mournful violin and piano. When he reasons today might be the day he finally leaves, I’m left to wonder if leaving is driving that Pontiac out of town, or waiting for Death to rejoin him with those German boys.
33. “I Can’t Make You Love Me”- Bonnie Raitt
Just because it’s a pop standard now, doesn’t mean it can’t crush me. Bonnie Raitt’s voice speaks to a time after a thousand lies have been told and all coyness drops away. Only a resigned bluntness remains over the smoky instrumentation. Raitt has always had amazing power in her voice, but it seems to go so frail as she admits “I will give up this fight.”
32. “Reminiscence”- Alice Sara Ott and Ólafur Arnalds
The Chopin Project was a strange and wonderful album. It reimagined a few classics from the master and added in original songs from Alice Sara Ott and Ólafur Arnalds that reflected Chopin’s themes. There would be no shortage of sad songs in the midst of music from the man who made “Funeral March,” but “Reminiscence” stands alone. It starts slowly, gracefully with a duet between violin and piano, before a mass of strings begin to rise in the background. They swirl with gaining momentum before they reach a tearful climax. Surely, something worthy of Chopin.
31. “Pink Bullets”- The Shins
There’s a common trope in indie/alternative/whatever music where peppy music is contrasted by despairing lyrical content. I call it “Shins Syndrome” thanks to The Shin’s tendency to mask sadness with major chords. No condition appears on “Pink Bullets,” it’s just all sad, all the time. “Pink Bullets” looks back at a high school romance, avoiding “the brutes in the halls” and finding small comforts in the hell that is high school. James Mercer admits that it’s “a movie so crass, and awkwardly cast/That even I could be the star.” But the two lovers must eventually leave. “When our kite lines first crossed, we tied ’em into knots/But to finally fly apart, we had to cut them off.”
30.“The Funeral”- Band of Horses
Yeah you knew this was eventually going to come up. It’s been on a million TV shows, soundtracked a million more break ups and generally was the sad song of choice for highschoolers the world over during the mid-2000s. But damn if it still doesn’t move. The small details don’t matter much, outside of a “billion-day funeral.” Instead “The Funeral” relies on Ben Bridwell’s keening, perfect voice and massive power chords equally at home at a stadium as they are in a bedroom cry fest. Put the lighter up as the tears roll down your face.
29. “Pale Blue Eyes”- The Velvet Underground
Lou Reed always had a knack for delivering his songs with detached sleepiness. From Venuses in fur to drug addiction, he had that cool apathy that a billion rock n’ roll bands would try to copy but never capture. Turns out that aloofness can only hide a broken heart for so long. Over one of The Velvet Underground’s most minimal tracks, Reed carries on an affair with a married woman, trying to convince himself he’s not in love. “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.”
28. “Everything Hits at Once”- Spoon
Spoon are really good at slogans. Like these little phrases that pop up in their music that get stuck in your head: “Auction off what you love/It will come back sometime;” “Do you want to get understood?” “She never been to Texas/Never heard of King Kong.” It’s all catchy stuff. But years before that they were making one of saddest stanzas in indie rock. Over a noir-like groove, Britt Daniel gives a hoarse wispier to an ex lover and gives out his heart. “I go to sleep and think that you’re next to me.”
27. “Ghost”- Indigo Girls
If I could steal the lyric writing talents of one person, I’d be hard pressed to find a better target than Indigo Girls’ Emily Saliers. She’s one of those songwriters that can fill full worlds with just a few lines of text. “Ghost” creates a lush history for two lovers in the aftermath of “adolescent wars.” I could teach a class on how brilliant this line is: “The Mississippi’s mighty but it starts in Minnesota at a place where you could walk across with five steps down/and I guess that’s how you started like a pinprick to my heart.” And Saliers’ harmonies with Amy Ray are as perfect the lyrics.
26. “All We Love We Leave Behind”- Converge
So the dog dies at the end (again). “All We Love We Leave Behind” is undoubtedly the heaviest song musically on this list and its wall of sadness matches the decibel levels, maybe even exceeding them. The mourning, rumbling bass sets the stage, the drums roll like war, the guitar is set ablaze and Jacob Bannon screams about the inevitability of death. “All We Love” is essentially a “touring is hell” song, but it evolves into so much more. Bannon is at first screaming about leaving his dog at home and not seeing her pass away (“You shook me from my sleep/That willed me to die”) but, by the second verse, “All We Love” sees every lover, every friend, every pet lost to the march of time. “I’m so sorry/That I missed your lives.”
