The 50 Saddest Songs of All Time

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40. XTC – “Dying”
XTC’s bassist and occasional songwriter Colin Moulding spent a lot of his compositional energy concerned with matters of getting old and passing away. For the most part, it’s a gentle obsession, as he assures himself in songs like “One of the Millions” and “Bungalow” that his sagging skin and greying hair are earned rather than thrust upon him. But on this song, found towards the end of XTC’s magisterial 1986 album Skylarking, Moulding lets all of his fears come right to the surface, spelling out in exacting detail the experience of watching a relative pass slowly away and not wanting to share that horrible fate. The music, for the most part, hangs back from his resigned vocals, clicking away like a bit of hospital machinery and only interrupted by a haunting piano roll and a fluttering bit of melodica.—Robert Ham

39. Robyn – “Dancing on My Own”
It’s probably safe to assume that Robyn advocates dancing your worries away, so it makes sense that she’d write a song that’s empowering in its self-awareness. She sums up those natural feelings of jealousy when an ex moves on to someone new sooner than expected. But instead of writing a dreary ballad about it, Robyn flipped the script. Though she’s watching her former love get frisky with his “new friend” in the club, the chorus doesn’t come across as self-pitying. Instead she triumphantly announces, “I keep dancing on my own.” The situation is undeniably hurtful and uncomfortable, but Robyn wants her audience to know that she’s going to be just fine alone, and you are too.—Tess Duncan

38. The Postal Service – “The District Sleeps Alone Tonight”
After one particular summer romance, I visited my girlfriend at her college two hours away, and the trip went horribly. From the time I arrived, I could tell she was over our relationship. So I can relate to Ben Gibbard’s narrator in “The District Sleeps Alone Tonight.” He probably had such high hopes his time in D.C., but it’s just left him unwanted and unloved and a little disoriented in a strange place where he clearly doesn’t belong. That feeling he’s having, I can personally attest to its level of suckiness.—Josh Jackson

37. Sun Kil Moon – “Carissa”
Benji is an album heavily focused on death. Of all the tragedies on the record, “Carissa” is the most gruesome and harrowing. Over some sparse, rumbling guitar plucks, Mark Kozelek memorializes Carissa, a mother who died in a fire at the age of 35. It’s a disturbing story made only more dismal when backing vocalists harmonize with Kozelek on lines like, “Carissa was 35/ You don’t just raise two kids and take out your trash and die.”—Tess Duncan

36. Tom Waits – “Anywhere I Lay My Head”
The moaning organ provides a steady accompaniment for Tom Waits’ gruff wailing on this desolate blues song. He delivers with anxiety-driven urgency, sounding like he could just break down into a blubbering frenzy at any moment. The horn section rides along smoothly in comparison, cresting and dipping deftly as Waits sings vigorously, wounds exposed. There’s no one who can pull off the palpable dejection of “I don’t need anybody, ’cause I learned to be alone” quite like Waits does.—Tess Duncan

35. The Smiths – “There Is a Light That Never Goes Out”
Oh, how to pick just one Smiths song for this list? Well, the most joyful moment of “There Is a Light That Never Goes Out” is when the narrator daydreams about a 10-ton-truck crashing into his car. Feeling unloved at home, he wants to escape with the one he loves, but he’s too scared to do anything about that love. Meanwhile, the keyboard line bounces happily along. In short, it’s the Smithiest of Smiths songs.—Josh Jackson

34. Elliott Smith – “Fond Farewell”
We could easily pull out half a dozen Elliott Smith songs for this list, and nearly that many were nominated. But when “Fond Farewell” was released almost a year to the day after his apparent suicide, this was the song that wrecked me. Smith wrestled his demons in his music, and “Fond Farewell” feels like his goodbye note in song. It’s filled with regret for the way things went. When he sings, “a fond farewell to a friend who couldn’t get things right,” it leaves you with a feeling of helplessness, wishing he were still here. That the words are set to his impossibly lovely melodies just makes it harder to hear.—Josh Jackson

33. Patty Griffin – “Making Pies”
A great song can help you see the world from a different perspective, as Patty Griffin often proves. The subject of “Making Pies” is a lonely spinster whose sweetheart died in the War. Bringing her mundane routine to life, Griffin’s song drips with the melancholy of a woman who’s accepted her fate (“I used to mind, but I don’t care ’cause I’m gray”) but can’t stop thinking of what might have been. “You could cry or die or just make pies all day,” she sings at the song’s conclusion. “I’m making pies.”—Josh Jackson

32. The Louvin Brothers – “The Angels Rejoiced Last Night”
“A house not a home is a picture Satan painted / for dear little sister ’n’ me,” opens the Louvin Brothers’ twisting, minor-key lament of a family near destitution from a no-good man’s high-timing. Mother prays. Father gambles, drinks, runs around. She begs him to repent. He refuses. Things get worse. Mother gets sick, prays, dies. Finally, father gets religion. Too late to ease his wife’s pain, shame or struggle. “Angels Rejoiced,” indeed. With their Appalachian twin harmony, it is the sorrow of the mountains distilled.—Holly Gleason

31. The Mountain Goats – “No Children”
This song leans a little harder on the angsty side of things, but it’s a lament-filled breakup song nonetheless. John Darnielle spends most of the song wishing ill upon his ex-lover, but it’s made even more severe by his wishes of suffering for himself. Winner for most upsetting lyric is hands-down: “I am drowning, there is no sign of land/ You are coming down with me, hand in unlovable hand/ And I hope you die, I hope we both die.” Darnielle’s sheer despondency and lack of any hope for a better tomorrow is what makes this track so disheartening.—Tess Duncan

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