The 50 Saddest Songs of All Time

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30. Pearl Jam – “Last Kiss”
Pearl Jam’s cover of the 1960s teenage tragedy song “Last Kiss” is heart-wrenching both because of its lyrics and Vedder’s performance. His warbling voice is perfect for the tone of the song—it’s not hard to believe that he’s heartbroken over the loss of his young love. Two teenagers are out on a date when they get into a terrible car accident and the narrator’s girlfriend dies in his arms. He begins with hope that if he lives a good life he’ll eventually see her in Heaven, but as he relives the events of the night that took her, he falls into despair. Both the lyrics and the music are simple, but its repetitive rhythm, steady beat and basic rhyme scheme just make it more relatable. In the second verse—”Something warm flowing through my eyes / But somehow I found my baby that night / I lifted her head, she looked at me and said / ‘Hold me darling just a little while’”—Vedder’s voice cracks on the final line, as the dying girl begs her boyfriend to hold her while she slips away. Vedder sings the final chorus with renewed agony and then hums a hymnal-like, wordless tune before the instruments and Vedder both fade into silence. “Last Kiss” captures pain and grief and wraps in a simple pop beat that’s hard to forget.—Danielle Ryan

29. Sinead O’Conner – “Nothing Compares 2 U”
As soon as Sinead O’Connor kicks things off with that mournful “it’s been seven hours and 15 days since you took your love away,” it’s not easy to refrain from picturing the iconic music video that accompanied this, the ultimate break-up song. That close shot of O’Connor’s face with the tears rolling down it will forever be etched into our memories, but there’s a second layer of sadness to “Nothing Compares 2 U.” Those are real tears O’Connor shed in the video, and she has stated that they were triggered by thoughts of her recently deceased mother thanks to the line “all the flowers that you planted, mama / in the backyard / all died when you went away.”—Bonnie Stiernberg

28. Justin Townes Earle – “Yuma”
Justin Townes Earle  named his 2007 debut EP for this searing, solo-acoustic suicide song. Over his claw-hammer finger picking, Earle lists a litany of afflictions—poverty, alcoholism, loneliness, klutziness, and lost youth and love—throughout a third person narrative. But in the bridge, Earle shifts the perspective to that of the omniscient narrator. He surmises in first person, “Lookin’ back I’d say it wasn’t so much the girl / as it was the booze and the dope and the way he took the weight of the world up upon his shoulders.” It’s this masterful balance of attention to detail—from naming the girl who broke his heart to describing the car that caught the weight of his jumper—and empathetic universality that makes so “Yuma” so fictionally affective, but realistically relatable.—Hilary Saunders

27. Sarah McLachlan – “When She Loved Me”
Everyone always talks about how Toy Story 3 destroyed them emotionally (and it did for me too), but the Toy Story scene that consistently breaks me up is the one from Toy Story 2 when Sarah McLachlan sings this Randy Newman song about a toy getting abandoned by her owner as she grows up. I’m not a big Disney/Pixar person, but I have a distinct memory of seeing the movie in theaters with my parents as a kid, looking over during this scene and noticing that even my dad was crying. Over a cartoon toy cowgirl getting left under a bed. And if that’s not brutal enough, the song fakes you out, filling you with false hope that its narrator will be loved again before revealing that her now-grown owner only picked her up to PUT HER IN A CARDBOARD BOX AND LEAVE HER ON THE SIDE OF THE ROAD. UGH, THE PASSAGE OF TIME. GETS ME RIGHT IN THE HEART.—Bonnie Stiernberg

26. Glen Campbell – “I’m Not Gonna Miss You”
At the beginning of 2011, Glen Campbell was diagnosed with Alzheimer’s disease. After a final tour the following year, the Grammy-winning country singer, TV host and actor recorded a farewell song for a the documentary Glen Campbell: I’ll Be Me, even as he could feel his mind slipping. The father of eight children from four wives, Campbell has been married to Kim Woolen for more than three decades. It’s to her that he addresses the painful refrain over and over in the song. “I’m never gonna hold you like I did / Or say I love you to the kids / You’re never gonna see it in my eyes / It’s not gonna hurt me when you cry / I’m not gonna miss you.” Knowing that Campbell was lucid enough to co-write and perform the song, feeling the truth of every word, and probably no longer is, is heartbreaking.—Josh Jackson

25. Bruce Springsteen – “The River”
Bruce Springsteen’s “The River” isn’t just sad—it’s absolutely soul-crushing. A brief summary of its events: a teen couple in a dead-end town accidentally get pregnant. There’s a shotgun wedding, and Bruce does all he can to remind us no one’s exactly psyched to be getting hitched (“for my 19th birthday I got a union card and a wedding coat” ... “no wedding-day smiles, no walk down the aisle, no flowers no wedding dress”). The narrator works construction, but there’s no work because the economy is terrible. Their relationship is a shell of what it once was, and memories of their early sparks “come back to haunt me, they haunt me like a curse.” And if that’s not enough, it also contains one of the biggest bummers of a line ever: “Is a dream a lie if it don’t come true, or is it something worse?”—Bonnie Stiernberg

24. Camper Van Beethoven – “All Her Favorite Fruit”
The desperate loneliness the narrator feels comes through in nearly every line of David Lowery’s lyrics, as he dreams of a girl out of his league. Sure there’s a bit of creepiness on the part of a guy who calls the object of his affection and never says a word, just imagining what she looks like on the other end of the line—especially since she already has a man in her life. All he can do is ride the train to an unfulfilling job and dream of all the places he wants to take her. Chris Pederson’s thumping tom drums measure out the mundane days while Don Lax’s violin counters the pitiful longing with a beautiful melancholy. You don’t have to dream of playing croquet or drinking your tea at four to feel the pain of unrequited love.—Josh Jackson

23. Townes Van Zandt – “Waiting Around to Die”
Stark. The echo chamber of a broken heart for a beat; dried twigs scratching at a cold window for a voice make Townes Van Zandt’s “Waitin’ Around To Die” a haunting more than a song. Beaten women, getting hustled, crime gone bad, jail time, addiction. Two minutes, 23 seconds of harsh reality, stoic in its acceptance of a fate worse than death.—Holly Gleason

22. Amy Winehouse – “Back to Black”
There’s never been a shortage of soulfulness in Winehouse’s songs, so it’s no surprise that she crafted such a painful breakup song. “Back to Black” recalls ’60s doo-wop with a moody, creeping tempo. The track’s massive sound contributes to the punch it packs—as the strings swell and fall, the brooding piano chords mingle with Winehouse’s grief-stricken vocals and pauses are filled in by spare tambourine shakes. Not many songs can sum up being dumped for an ex as well as Winehouse does when she woefully sings, “I died a hundred times.”—Tess Duncan

21. Neutral Milk Hotel – “Two Headed Boy Pt. 2”
It’s difficult to talk about “Two-Headed Boy Pt. 2” without talking about the album it brings to a powerful close, but I do believe that even without the context of In the Aeroplane Over the Sea, the song stands out as one of the most moving pieces of music in the past two decades. Like most of Jeff Mangum’s work, there are times when you have to put in some effort to parse the expressionistic imagery (“blister please with those wings in your spine…how he’d love to find your tongue in his teeth”) but at other times, the emotion is plain and jarring. “In my dreams you’re alive,” he sings, in that plaintive, keening, inimitable voice, and it builds to a climax that I, personally, find devastating: “When we break, we’ll wait for our miracle. God is a place you will wait for the rest of your life.” I can’t think of a better way to encapsulate the hope and fear and agony and grace of being alive. Nor can I think of anyone who can somehow express this inexpressible concept with such power and emotional precision quite like Mangum. At the song’s end, you can hear the scuffling sound of a chair as he rises and leaves—a subtle, poignant conclusion to one of the most singular, beautiful albums ever made.—Shane Ryan

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