It assures you that you’re not alone, that someone else has felt this pain and turned it into a gift for you. 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, A hauntingly beautiful tale of unrequited love, “Pale Blue Eyes” is about recognizing you’re being used and allowing it to happen anyway. Send us a tip using our anonymous form. 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. 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. She and her sister Alison Moorer are the “two little girls better off this way,” orphaned at 17 and 13 and sent off to live with relatives.—Josh Jackson, When it comes to sad songs, I can’t think of anything quite as powerful or heartbreaking as Vic Chesnutt’s “Flirted With You All My Life.” Chesnutt is a poignant figure in general—an Athens, Ga. legend who created wild, beautiful music until his death in 2009. 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. In her dying days, Sadako therefore worked on folding her own 1,000 cranes, but passed away having only completed 644. All he can do is ride the train to an unfulfilling job and dream of all the places he wants to take her. Like no other musical genre, country stories of loss and heartbreak turn the old “tear in my beer” cliché into a sad, salty reality. 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. The Velvet Underground – “Pale Blue Eyes”, 13. “Flirted With You All My Life” is sobering, addressing death directly: “Oh death, oh death, oh death / Really, I’m not ready.” It relates his own experience with dying, whether through his lifelong flirtation with suicide or his mother’s battle with cancer, and it’s that honesty paired with Chesnutt’s colorful past that will make you question and almost certainly cry—in public, for the public or for life’s adventure in general.—Brittany Joyce, Mike Hadreas’ songwriting is unabashedly raw, the kind that speaks about the dirty and the unsightly in a way you can’t ignore.
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. With his deep, hang-dog voice, Stephen Merritt can no longer imagine that the sun would even bother to shine on a world where his love is gone. Sufjan Stevens – “Casimir Pulaski Day”. She sums up those natural feelings of jealousy when an ex moves on to someone new sooner than expected. That feeling he’s having, I can personally attest to its level of suckiness.—Josh Jackson, Benji is an album heavily focused on death. When the narrator looks at the body of the girl he loves after she finally succumbs to cancer, he thinks for a moment that he sees her breathing. Although it might sound counter-intuitive, listening to sad music when we’re sad can actually help us out of our funk.
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. 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. This is a song that more people should know, but that no one else should ever attempt to cover.—Josh Jackson, “Everybody Hurts” is one of the rare songs on this list that actually offers catharsis. Nafrat Ki Duniya Ko Chhod Ke. It’s written from the perspective of his deceased grandfather, who implores his still-living wife to “sleep oh sleep, my Vivian” because “heaven is too cold without you.” I mean, come on. In This Article: Hank Williams – “I’m So Lonesome I Could Cry”, 1.
In Cash’s hands, it’s a death-bed confessional.—Ryan Reed, The sorrow behind this Hank Williams classic is heightened by the way each grief-stricken element of the song comes together. Bernie Taupin captured this sentiment best and hid it in a jaunty little pop song by Elton John: If someone is suffering enough to write it down GETS ME RIGHT IN THE HEART.—Bonnie Stiernberg, At the beginning of 2011, Glen Campbell was diagnosed with Alzheimer’s disease. “I’m making pies.”—Josh Jackson, “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. Glen Campbell – “I’m Not Gonna Miss You”, 24. A brief summary of its events: a teen couple in a dead-end town accidentally get pregnant. Smith wrestled his demons in his music, and “Fond Farewell” feels like his goodbye note in song. The Postal Service – “The District Sleeps Alone Tonight”, 35. 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, 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. And these 50 songs helped the Paste staff to hurt so good. Cohen has a way of invoking deep spiritual longing with Biblical references that turn extremely personal, and Buckley had a way of drenching it all in tremulous emotion. “Angels Rejoiced,” indeed. 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. 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. 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, Pearl Jam’s cover of the 1960s teenage tragedy song “Last Kiss” is heart-wrenching both because of its lyrics and Vedder’s performance. There’s the song about the band on the Titanic, playing as the ship sinks. 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. It’s the ultimate mockery to compensate for (and attempt to comprehend) our irrevocable finality.—Hilary Saunders, That molten caramel voice drenches an acoustic guitar.
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