The 50 Saddest Songs of the 21st Century (So Far)

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The 50 Saddest Songs of the 21st Century (So Far)

A few years ago, Paste looked at the 50 saddest songs of all time, but as the need for new music to help you grieve—to show you that you’re not alone in your pain and to give you the space to process sorrow—is unending, we asked our staff and writers what songs they return to in times of sadness. It didn’t take long to get responses. We all have our go-to sad songs, like security blankets for those all-too-common times of need. So grab a pint of your favorite ice cream and your best pair of headphones and queue up our playlist for your pain. We kept it to one song per artist, though several had multiple nominations. —Josh Jackson

This list has been updated from its original publish in 2018.

Here are the saddest songs of the 21st century so far:

50. Bright Eyes: “At the Bottom of Everything”

Don’t be fooled by one of the jauntiest melodies Conor Oberst has ever written. Introduced as a song sung from one passenger to another on an airplane plummeting into the sea, it’s a call to resistance, but an utterly ironic one. Every clever, colorful verse teases a course to victory while stoically accepting defeat: “We must blend into the choir, sing as static with the whole/ We must memorize nine numbers and deny we have a soul/ And in this endless race for property and privilege to be won/ We must run, we must run, we must run.” Joy in the face of hopelessness or the existential equivalent of gallows humor, it’s a nihilistic glimpse into the empty void that ends: “Oh my morning’s coming back/ The whole world’s waking up/ All the city buses swimming past/ I’m happy just because/ I found out I am really no one.” —Josh Jackson

49. Mount Eerie: “Real Death”

Following the passing of his wife, visual artist and musician Geneviève Castrée, Phil Elverum took a couple months to grieve and then sat down in the room where she died and recorded the 11 songs that make up A Crow Looked at Me. Song by song, line by line, he speaks directly to her and into her absence. The results are as engrossing as they are emotionally devastating. Opening with a clarification that death shouldn’t be reduced to art, that the true experience of it is too profound to turn into music, he goes ahead and does just that on “Real Death.” Singing over electric guitar strums and a droning accordion, he describes the immediate aftermath of Geneviève’s dying, how rooms feel empty now, how she still gets mail. After receiving a backpack for their infant daughter that Geneviève ordered shortly before her death, he collapses on the porch in tears. “It’s dumb and I don’t want to learn anything from this,” he sings over the final strums. “I love you.” The whole album makes everything else seem frivolous while you’re hearing it. How often you want to do that will depend on how comfortable you are staring into the face of real death. —Matt Fink

48. SZA: “Drew Barrymore”

Months before SZA dropped her hotly anticipated debut studio album Ctrl, “Drew Barrymore” introduced listeners to precisely how Solana Rowe’s Pop Album of the Decade contender would sound. With psychedelic production, percussion equally indebted to indie rock and jazz, and peripheral strings fit for a true R&B tearjerker, “Drew Barrymore” aptly previewed Ctrl and provided the ideal playground for SZA’s nimble-as-Jack voice, which can somehow move with a rap cadence and employ a gently rattling vibrato in the same breath. The track is among the most candid on an album revered for its honesty: As SZA sings about envy, loneliness, and inflated female beauty standards, she embodies an outcast character like those the song’s titular actress has often played. “Why’s it so hard to accept the party is over?” SZA asks at the song’s outset, and at the track’s end, listeners will wonder the same. —Max Freedman

47. Jesse Malin: “Downliner”

After fronting New York glam-punks D Generation with a gleeful sneer for most of the ’90s, Malin mined a more sorrowful sound on his first solo LP, The Fine Art of Self Destruction. “Downliner” is one of the standout tracks, a rueful meditation on dissatisfaction and regret. Malin sounds resigned as he sings about lingering “funny memories” and contrasts them with a bleak present and hopeless future. “You and me, you know we don’t talk much/ It’s hard to handle something you can’t touch,” he sings. That’s a perfect account of how even amicable breakups can leave lasting scars, and Ryan Adams’ clanging electric guitar riff evokes the noise that underscores heartache and echoes around inside your head late at night when the rest of the world is quiet. —Eric R. Danton

46. The Head and the Heart: “Rivers and Roads”

Folk songs are especially good at stirring up emotion, and the first line of this acoustic tear-jerker from The Head and the Heart’s self-titled debut is enough to inspire a buyout of Kleenex stock: “A year from now we’ll all be gone, all our friends will move away.” Lyrics predict those friends will be off to “better places,” perhaps to new cities and careers, but the impending loneliness and separation take emotional control from congratulations’ grasp. “Rivers and Roads” is about change, and about missing people. And while those feelings can be profoundly sad, the song doesn’t necessarily leave the listener in a dark place: You might find yourself smiling through the tears, rather than heaving through a series of weeps, as its gentle tempo is drowned out in a rumbling of keys and voices. Ideal for listening after a college graduation or prior to a cross-country move, “Rivers and Roads” is a bittersweet reminder that some relationships are always in reach. —Ellen Johnson

45. Jason Isbell: “Elephant”

This one is truly difficult to withstand without crying, but the visceral reactions that “Elephant” incites are why this song is so everlasting. It’s been called “the saddest song ever,” and while it’s certainly not chipper, there’s something very beautiful about the ease with which Isbell sings about life-altering topics such as grief, death and cancer. As this character is withering away due to cancer’s effects, everyone tries to ignore the “elephant” in the room and just make her final moments as joyful as possible. —Ellen Johnson

44. Sharon Van Etten: “Afraid of Nothing”

Sharon Van Etten took her affinity for sad songs to a new level on her 2014 album Are We There, an anguished collection as mesmerizing as it is heartbreaking. First song “Afraid of Nothing” lets you know up front exactly where she’s going. The minor-key piano chord that opens the tune is the musical equivalent of a catch in your throat, as if to prepare you for what is to come. Then she gets to the refrain: “I can’t wait ’til we’re afraid of nothing,” she sings, and it’s honest and brutal as Van Etten begins the exquisitely painful work of detaching herself from a relationship where one, or maybe both, of them is always holding something back. While Van Etten sometimes sounds distraught on Are We There, and sometimes hollowed out by emotion, she is quietly, sorrowfully sure of herself on “Afraid of Nothing.” There’s no going back, she seems to say, and pushing forward is going to hurt, a lot. —Eric R. Danton

43. Neko Case: “Sleep All Summer”

Eric Bachmann wrote this mournful duet for Crooked Fingers’ 2005 release Dignity and Shame, and sang it with Lara Meyerratken. Neko Case makes it her own on her latest album Hell-On. Case sings with subdued clarity, her power held in reserve. Bachmann’s voice is stronger and more resonant than on the earlier version, which featured acoustic guitar instead of the piano that carries the song here. Together, Case and Bachmann sound at once wounded and bewildered, as though their characters know full well that their bond is crumbling and are powerless to stop it. They sing with a tenderness that is shattering, and their regret is almost palpable as they disentangle themselves from each other. Neither singer is a slouch when it comes to writing sad songs—see also, “I Wish I Were the Moon” by Case, or most of the songs on Dignity and Shame— but the two of them together are a potent combination. —Eric R. Danton

42. Earl Sweatshirt: “Chum”

Less than a year after he returned from boarding school in American Samoa to countless “Free Earl” chants, Earl Sweatshirt released “Chum,” his first proper single ahead of his debut album, Doris. But instead of addressing his musical exile in the South Pacific for his comeback song, he responded with a heartbreaking tale over sinister beats about growing up without his father. Earl says he could never really fit in at school, unable to explain his feelings toward his dad as a child: “And I just used to say I hate him in dishonest jest/ When honestly I miss this n***a, like when I was six/ And every time I got the chance to say it I would swallow it.” This lead him towards drinking heavily and later wanting to call it quits on his burgeoning career after years of “brush[ing] the dirt off [his] psyche.” Thankfully, his experience led him to bond with Tyler, the Creator, who also shared a similar father-less upbringing. —Steven Edelstone

41. John Moreland: “Blacklist”

“Just let me find a place where I fit,” Moreland pleads at the end of “Blacklist,” a wrenching paean to unrequited love and misbegotten rebellion that the Oklahoma musician sings in a rough, weary baritone. The song is a study in contrasts, as nostalgia faces off against fading idealism and a dose of hard truth in lyrics that never pull a punch. Moreland displays a rueful fondness for his younger self, even as he winces at how life can drain away the innocence and enthusiasm of youth until all that’s left is cynicism and uncertainty that we cover with false bravado. “The older I get, you know/ Truth, it gets harder to find,” Moreland sings, describing a life lesson that never stops being true. As bleak as his songs can be, Moreland’s most recent album, Big Bad Luv, has a slightly more contented tone. Yet it’s his sad songs that resonate the most, maybe because we need them more. —Eric R. Danton

40. Superchunk: “Me & You & Jackie Mittoo”

“Me & You & Jackie Mittoo” doesn’t sound sad at first. It’s a short, hook-filled blast of nostalgia about hitting record shops with your friends and driving around in the summer listening to reggae, and perhaps the leanest and most direct pop song Superchunk’s ever made. When you really listen to the lyrics, though, and hear those final lines—”I hate music/ What is it worth?/ It can’t bring you/ back to this earth”—you realize this seemingly sunny song about youth is a eulogy for a lost friend. Music is a potent force—it can create friendships and help us get in touch with our feelings, both as listeners and creators—but as all-powerful as it feels when you’re hanging out with your friends in your teens, its limitations grow impossible to ignore with time and age. Superchunk’s frontman Mac McCaughan can sing about the music he listened to with his friends, can sing songs about them, both in life and death, but no matter how much it means to him, that music can’t fill the space left by his friend’s absence. “Me & You & Jackie Mittoo” might only be two minutes long, but those are probably the most heartbreaking two minutes in Superchunk’s 30-year career. —Garrett Martin

39. Snail Mail: “Pristine”

Indie rock wunderkind Lindsey Jordan and her band, Snail Mail, released their debut album in 2018, Lush. “Pristine” continues the personal, intimate feel of Jordan’s debut Habit, which was written in her suburban Maryland bedroom. But “Pristine” aims a bit higher, with soaring choruses and crisp guitars crafting a shimmering backdrop for Jordan’s musings on young love. “Don’t you like me for me?” she sings. “I know myself, I’ll never love anyone else.” Ah, to be young. And yet, “Pristine” was a grand step forward for a promising songwriter who—despite the continued hype—is really just getting started. —Loren DiBlasi

38. Bon Iver: “Skinny Love”

Justin Vernon recorded this song one winter in a cabin in the woods of northwestern Wisconsin, and it sounds like it: His acoustic guitar and double-tracked falsetto vocals are hushed and intimate, like the glow in a distant window in the midst of a snow-covered landscape. The song is about staying in a relationship for the wrong reasons, and regretting the pain that inevitably results—a theme on his first album as Bon Iver, 2007’s For Emma, Forever Ago. Vernon wrote the album after a disillusioning stint fronting a band in North Carolina and battling health problems including pneumonia, and then mono. He retreated to his family’s cabin planning to regroup for a few weeks, and ended up staying there for three months while working on the songs that became For Emma. “Skinny Love” was the first single, and the tune that helped launch Bon Iver into the public consciousness and make Vernon into a reluctant indie-rock star, a record producer (Kathleen Edwards, the Blind Boys of Alabama), creator of the Eaux Claires music festival and, not least (if perhaps least likely), a musical collaborator with Kanye West. —Eric R. Danton

37. Rebekah del Rio (with David Lynch and John Neff): “No Stars”

Serious audiophiles will point out that one of the saddest things about this song is the intrusively obvious pitch correction in the version used in Episode 10 of Twin Peaks: The Return (bummer), but setting aside that technicality, “No Stars” is still a heartbreaker even by Twin Peaks standards. Co-written and produced by the literally-inimitable David Lynch, it’s a lyric meditation on desolation and the grief of lost intimacy. Playing with the expression “stars in your eyes,” the lyric mourns a relationship, and a world, from which the light has vanished. Lynch’s signature themes are much in evidence: Nostalgia, expressed in the lyrics and also in the drawn-out 3:4 tempo. Electricity (the slow thrumming brushwork on the drums almost seems to sizzle). The cheek-to-cheek slow-dance of love and extinction, romance and violence, mystery and piercing directness, emotional overflow and bleak emptiness. In the context of the episode, in which it is set off like a jewel in a ring, it’s especially agonizing (it’s juxtaposed with a major-league ave atque vale monologue by the dying Catherine Coulson, and onstage del Rio appears in a dress with an “owl cave” motif against a rippling Black Lodge-style red velvet curtain) but you don’t have to be a Twin Peaks fan or remotely have the extra freighted symbolism to feel the raw longing in that powerhouse voice (Autotuned though it might be), or to feel the throwback-’50s ballad vibe suffusing the track with sorrow at the death of a more innocent world “where it all began/ on a starry night” and we felt safe and encircled and loved. Lynch has always loved to flirt with melodrama, and this torch song found its perfect expression in del Rio’s full-throated, bell-like voice. I defy you to listen to this song and not feel desperate for a return to a glittering moment of young love and infinite possibility. —Amy Glynn

36. 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

35. Brandi Carlile: “That Year”

This deeply personal song from Brandi Carlile, set to the quiet strumming of guitars and shuffling drums, remembers a friend who committed suicide when she was a teenager—and all the confusion and sadness and rage that comes with tragedy. She’d never been able to forgive and had put the whole event out of her mind for years. But the final verse sums up Carlile’s reconciliation, allowing her to finally grieve: “I was angry/ I was a Baptist/ I was a daughter/ I was wrong.” —Josh Jackson

34. The National: “About Today”

If “About Today” is any indication, The National know a thing or two about regret. Matt Berninger and co. are gurus at crafting noirish, depressive rock songs, but “About Today” reigns as one of the sharpest. Backed by locomotive acoustics, Berninger recalls a troubling day in the life of a relationship. She was distanced, but he didn’t ask why. “What could I say?” Berninger bellows. “I was far away.” Reckoning with the realization that he may lose her because of his inability to communicate, the protagonist is helpless. Meanwhile, we’re over here reaching for a second hanky. —Ellen Johnson

33. Death Cab for Cutie: “What Sarah Said”

While the traditional marriage vow includes a mention of “in sickness and in health,” we tend to always focus on latter—weddings are happy occasions after all. But on the piano-led “What Sarah Said,” Ben Gibbard deals with the former, envisioning the very end of his future marriage, where he’s staring at his shoes in the ICU. “Love is watching someone die,” a quote from his friend Sarah, sings Ben Gibbard virtually a capella before asking, “So who’s gonna watch you die?” Sure, this is a love song at its heart, but in a dark and twisted way—“What Sarah Said,” one of the highlights on Plans (which includes another saddest-song contender “I Will Follow You Into the Dark”), envisions the strength of love in the emergency room, “a place where we only say goodbye,” decades into a relationship when it is—quite literally—on life support. —Steven Edelstone

32. LCD Soundsystem: “All My Friends”

When I hear those first few bars of jittery piano, I know I’m about to be emotionally wrecked. “All My Friends,” though danceable and streamline in nature, relays a universal sadness about getting older and the fluctuation of friendships as we age. Rarely will you find an LCD Soundsystem fan who doesn’t have some attachment to the track, which is sad to many for many different reasons. At home in both a sweaty Brooklyn dancehall or your living room, “All My Friends” isn’t exactly dismal, but it’s certainly upsetting. James Murphy questions someone’s priorities when he sings, “You spent the first five years trying to get with the plan/ And the next five years trying to be with your friends again,” but he switches to first person by track’s end, singing, “If I could see all my friends tonight.” Before cranking this one up, make sure your closest pals are on speed dial. —Ellen Johnson

31. Radiohead: “True Love Waits” (2016 version)

When Thom Yorke wrote “True Love Waits” in 1995, it was an acoustic love song for his partner of a few years, Rachel Owen. When the album version was finally released 21 years later, a melancholy piano ballad complete with ambient sounds throughout, they had recently broken up and Owen was diagnosed with the cancer that killed her later that year. The track is a brutal listen; Yorke’s vocals, while probably the clearest on the entirety of A Moon Shaped Pool, feel distant, like he’s looking back on the song as a bittersweet memory from long ago, now knowing what would eventually come next. His pleads of “Just don’t leave,” which used to be playful and romantic on the 2001 live version that was released as a part of the I Might Be Wrong—Live Recordings, take on an entirely different meaning in 2016, yearning for a happier and simpler time that has long since passed. —Steven Edelstone

30. Lori McKenna: “People Get Old”

You can try to hold it together on this song from McKenna’s album The Tree, but her loving portrait of her aging father is so rich with detail and so matter-of-fact way that there’s an excellent chance McKenna will have you all choked up by the end. At heart, “People Get Old” is a joyful song, as McKenna celebrates a lifetime’s worth of memories with her dad, who turns 83 this year. But her plain-spoken observations about the ways in which we become our parents, and our kids become us, are heartbreaking at their core. “You live long enough and the people you love get old,” she sings, and all too soon, they’re gone. It’s just life, and it goes inexorably onward, but sometimes—hell, usually—the people we love are gone before we’re ready to let them go, and who is ever really ready? —Eric R. Danton

29. Angel Olsen: “Windows”

This is a sad song with a secretly positive message. “Windows” is wistful but more for its instrumental composition and Olsen’s gossamer vocals. Just a few soft riffs and gentle drum hits are all that’s needed to back the wavering twang in her voice as she encourages a friend to move on from their dark past. Though it sounds like she’s singing through trembling lips, Olsen’s spirit is uplifting. There are loads of upbeat songs with depressing lyrics but “Windows” does the opposite, inducing tears despite its bright imagery.—Tess Duncan

28. The Avett Brothers: “No Hard Feelings”

This song, one of the more explicitly serious in The Avett Brothers’ sweeping catalogue, is not about the apocalypse. But listen to it enough times, and Judgement Day imagery will begin to unfold. “No Hard Feelings” is about dying with no regrets, about the day when one’s soul leaves their body and all that’s left to focus on is the joy that defines a life. Or, as Seth puts it, “Holding the love I’ve known in my life.” This is an end-of-the-world song for the faithful folks who just believe everything works out the way it should. It’s about making peace with your “enemies” and learning to appreciate life while it’s happening, in both its “loveliness” and “ugliness.” Do that, and then when the end really does come, all that’s left is “just Hallelujah.” —Ellen Johnson

27. Shelby Lynne: “Heaven’s Only Days Down the Road”

Written a quarter century after her father shot and killed her mother then himself in the driveway of their home in Monroeville, Alabama, the hurt still feels fresh for singer/songwriter Shelby Lynne. Sung from the perspective of her father a few days before his death (“I been insane since I was nine / Never was the cryin’ but the fightin’ kind / Load up the gun full of regret / I ain’t even pulled the trigger yet”), the driving blues rhythm feels frantic as we all know how the story ends. 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

26. Vic Chesnutt: “Flirted With You All My Life”

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. But it’s through songs like this one that he transcends even that. “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

25. Perfume Genius: “Mr. Peterson”

Mike Hadreas’ songwriting is unabashedly raw, the kind that speaks about the dirty and the unsightly in a way you can’t ignore. He puts a traumatic experience into words that sound like poetry—they’re arranged in such a way that it’s almost just as heartbreaking to read them on paper as it is to hear Hadreas tenderly singing them. But it wouldn’t have quite the effect without that bleak, pulsating piano line.—Tess Duncan

24. Iron & Wine: “The Trapeze Swinger”

I still remember the exact spot where I first I heard “Trapeze Swinger,” which is pretty unusual for me—I have a decent memory for where I’ve read certain unforgettable books, but songs tend to blend in space and time, since you can listen to them over and over and gradually erase the point of origin. But “Trapeze Swinger” made such an unforgettable impression that the setting remains locked in my head—senior year, central campus apartment, sitting in front of my computer with AIM running, heartbroken. This song hit me at the perfect time in life, and seemed to capture a kind of ineffable melancholy that went beyond the girl I was pining over, and was instead an essential part of the human experience. Like most great songs, the lyrics alone don’t tell the story, but the simple refrain gets at the heart of the temporary nature of our lives contrasting with our human urge for permanence: “Please remember me.” Beam’s voice is at its most nostalgic here, and he tells the story of a boy and girl who connected and blew apart, complete with circus imagery, snippets of memory, and the bright, painful moments of consummation and separation. The song’s narrative ranges from heaven to hell, and represents Beam’s most ambitious poetry—it’s long, it meanders, and it hits you with a desperate intensity. Great art doesn’t necessarily tell you something new, but rather puts words to something you always knew, but couldn’t name. Here, Beam has accomplished nothing less than telling the story of our sadness.—Shane Ryan

23. St. Vincent: “New York”

Few lyrics have resonated more this decade than “You’re the only motherfucker in the city who can handle me.” But “New York’s” strength doesn’t necessarily come from its refrain as much as its hyper-specific ode to Manhattan crossed with a breakup song. From callouts to Astor Place (she even spins in the Astor Place Cube in the music video!) to 1st and 8th Aves, Annie Clark bemoans the loss of a lover—presumably her ex, Cara Delevingne—and her friends, who like many in the arts community this decade, packed up their belongings and moved to Los Angeles. The piano ballad is easily the best song about New York released in some time, miles more emotionally affecting than the Google Maps-like, landmark-referencing “Empire State of Mind,” and it’s one that does a lot with a little, stripping away Clark’s manic guitar-playing in such a way that you almost forget she’s still the best guitarist of her generation. —Steven Edelstone

22. 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

21. Laura Marling: “Night After Night”

“Darling I loved you” opens up Side B of Laura Marling’s pitch perfect third album, A Creature I Don’t know. The past tense of that opening line, whispered and bitter, sets the tone for “Night After Night,” a track about a woman becoming increasingly detached and indifferent throughout a relationship that overstays its welcome by years, possibly decades. The glacially slow breakdown of their love coincides with the decay of the subject’s body and mind: “Night after night, day after day/ Would you watch my body weaken/ And my mind drift away?” goes the reprise, sung by a mournful Marling. The subject just feels worn-out and drained, done in by a daily routine where, “He screams in the night, I scream in the day/ We weep in the evening and lie naked and pray.” While most of the breakup songs on this list deal with the sudden and sharp feeling of heartbreak the moments and days after a relationship is finished, “Night After Night” is the opposite—here, Marling portrays a lover not at the end of her rope, but years after the rope has all but disappeared. —Steven Edelstone

20. John Prine: “Summer’s End”

Not many artists can say they wrote some of their best songs in the last three years of their career. But John Prine, as it is abundantly clear, wasn’t most artists. He captured an overwhelming sadness seasoned with hope in his 2018 song Summer’s End, from The Tree of Forgiveness, his last album. The lyric sheet could read like a musing on death, an invitation from an estranged family member to mend broken ties, a note from a longtime lover or partner post-conflict, or, if you’re of the spiritual type, even the call to return to one’s rightful home with God. “Come on home,” he sings over and over. “The moon and stars hang out in bars just talking,” Prine adds. “I still love that picture of us walking.” It’s not flashy, but it’s beautiful, and leaves the door wide open for a listener’s interpretations. —Ellen Johnson

19. 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

18. Frightened Rabbit: “Poke”

“I have such an appreciation for people who discuss the ugliness of love,” Julien Baker (who also appears on this list) explained in an interview about Frightened Rabbit’s 2008 magnum opus, The Midnight Organ Fight for the Village Voice (RIP). “I feel like sometimes, we don’t get to the gritty imagery of that ugliness… It’s just crazy how you feel so embedded in the scene that [Scott Hutchison is] constructing for you.” The album follows the late Hutchison attempting to break up with his longtime on-again-off-again girlfriend, always coming back for another bout of self-inflicted masochism. The record comes to a screeching standstill on “Poke,” a heartbreaking stunner of an acoustic fingerpicked track, where he details the process of finally cutting the chord, delving deep in the ugliness that Baker spoke about with some of the most brutally honest yet beautiful breakup lyrics in recent memory. “But like a drunken night, it’s the best bits that are colored in,” he croons in his Scottish brogue before launching into perhaps the most tear-inducing stanza of the indie rock era, ending with a line that he routinely would scream live: “You should look through some old photos/ I adored you in every one of those/ If someone took a picture of us now they’d need to be told/ That we had ever clung and tied/ A navy knot with arms at night/ I’d say she was his sister but she doesn’t have his nose/ And now we’re unrelated and rid of all the shit we hated/ But I hate when I feel like this/ And I never hated you.” —Steven Edelstone

17. 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

16. 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

15. 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

14. 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

13. Julia Jacklin: “Don’t Know How to Keep Loving You”

“Don’t Know How To Keep Loving You,” what Jacklin says is her favorite song on her excellent 2019 album Crushing (even though “that changes everyday”), is a revelation. Studded with bluesy, cathartic guitar solos, it’s a song about being trapped in comfort, about chasing a sun you know is going to set anyways. “Don’t know how to keep loving you,” she sings. “Now that I know you so well.” But, again, as on the rest of the album, Jacklin marches fearlessly ahead, through the pain, the loneliness, “into the darkness, or is it the light?” This is one of those songs that leaves me wondering, “How does she get on stage every night and bear her whole, entire soul?” —Ellen Johnson

12. 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

11. 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

10. Phoebe Bridgers: “Funeral”

Self-proclaimed adopter of the sadcore genre, indie folk crooner Phoebe Bridgers knows how to write a melancholic tune. Her 2017 album Stranger in the Alps is replete with mournful ballads and stories of longing and loss, but “Funeral” may just be the most woeful. She sings about the devastating death of a friend and the survivors who help her through it. Though a warm display of fingerpicking and pedal play, there’s no light at the end of this song’s tunnel: Bridgers addresses her depression as she wails, “Jesus Christ, I’m so blue all the time/ And that’s just how I feel/ Always have an always will.” “Funeral” is a brave declaration of grief and likely requires a lot of courage to perform. It’s easy to forget that a beautiful song may only exist because an artist has suffered, but in “Funeral,” the listener, too, is in the trenches. —Ellen Johnson

9. 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

8. 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

7. Frank Ocean: “Self Control”

Compared to the larger-than-life characters that populated Frank Ocean’s 2012 masterpiece channel ORANGE, the scope of his follow-up Blonde is more interior, laden and tangled with the mental back-and-forths that plague relationships: heartbreak, desire and doubt. Nowhere is this clearer—that is, clear by Blonde’s cryptic standards, an album without a singular recognized spelling for its title—than on “Self Control.” With a pitched-up intro reminiscent of Prince’s “If I Was Your Girlfriend,” the track oozes lust before abruptly transitioning that longing into something more mournful, repositioning Ocean as squarely exterior to someone else’s relationship. With a nonchalant “Keep a place for me / I’ll sleep between y’all, it’s nothing,” Ocean seemingly brushes off the nostalgia for what he had, though the lush, underwater arrangement of the song that follows suggests otherwise. Despite that the title of “Self Control” is a reference to choosing composure over vulnerability, the track is fragmented and indecisive, aching most in the moments where Ocean lets his slip. —Katie Cameron

6. 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

5. David Bowie: “Blackstar”

David Bowie timed the release of his final album to coincide with his 69th birthday. Two days later he died, to the total shock of all but those closest to him. Blackstar’s valedictory title track isn’t just an epic Sad Song because of the timing, though-and it isn’t just a sad song, though it had me in tears the first time I heard it. The elusive (and allusive) lyrics oscillate between dissonant, moaning chant sections, meditative pop and witty swagger (including a parting swipe at Snarkoholic novelist Martin Amis, who has had his loafer firmly in his mouth ever since he called Bowie a “flash in the pan” in 1974 (Bowie’s rejoinder, “You’re the flash in the pan (I’m not a Marvel star); I’m the great I-Am…” seems to get DC’s Barry Allen mixed up with Marvel’s Quicksilver but I’m sure Amis had some toothmarks in his gabardines anyway). The ten-minute track might not be, as people thought at first, a specific farewell message to fans (Blackstar was conceived and in production before Bowie knew his cancer treatment had failed), but it is certainly a meditation on fame, posterity, and standing at the strange crossroads of age (69 isn’t spectacularly old but Bowie’s prolific multi-persona career had spanned over five decades, and that’s a hell of a long time in rock). It’s melodically poignant, vocally burnished, arranged in a way I can’t not call “stellar,” and a kaleidoscopic exploration of his lifelong master trope: Stars, literal and figurative. (A black star is, among other things, a theoretical star that has gone out, and has mass but no energy; it’s also a type of cancer lesion.) Blackstar is the wise and self-aware work of a mature artist but retains Bowie’s almost childlike spirit of wonder at the vastness and weirdness of what we cannot perceive-at least not while we’re in our bodies. The combination of craft and chance at work in this song are a dazzling reminder that a real craftsman can make art even of his own death. And of what the world lost in January 2016: An intergalactic traveler, and a superstar. —Amy Glynn

4. Julien Baker: “Go Home”

“It took me awhile to for me to be able to do ‘Go Home’ comfortably because that’s one of the most explicitly autobiographical songs,” Baker once told me while touring off of her first record, Sprained Ankle. It’s easy to see why this one in particular was so tough for her to play live—“Go Home,” the album’s final track, is a slow-burning piano ballad where Baker details her lowest point, pleading to God while drunk (and likely much worse) in a ditch on the side of the road. Written about her experience at the height of her previous battle against substance abuse—“there’s more whiskey than blood in my veins/ More tar than air in my lungs”—all she wants is for someone, anyone, to provide a helping hand and get her safely back into her bed for the night. Even at home, her friends have reason to still worry (“‘Cause I know you’re still worried I’m gonna get scared again/ And make my insides clean with your kitchen bleach/ But I’ve kissed enough bathroom sinks to make up for the lovers that never loved me”). It all culminates in the simple yet devastating final line, a screaming appeal toward a higher power—one that she can barely fully get out—“God I wanna go home.” —Steven Edelstone

3. Adele: Someone Like You

Adele’s 21—and really, most of her catalog—is full of heartbreak. There’s a particular kind of braveness unique to anyone who can get up on stage and sing through your tears about an ex for whom you still hold a flame. After she first performed “Someone Like You” on Later, with Jools Holland in 2010, she told ITV2, “I was really emotional by the end because I’m quite overwhelmed by everything anyway, and then I had a vision of my ex, of him watching me at home and he’s going to be laughing at me because he knows I’m crying because of him, with him thinking, ‘Yep, she’s still wrapped around my finger.’” Fortunately, the audience’s response to all that glorious beauty in her sorrow brought her out of her misery. But the bittersweet chorus is the best encapsulation in this young century of the misery of lost love—that particularly feeling of loneliness when someone you care for chooses to be with someone else. —Josh Jackson

2. Johnny Cash: “Hurt”

Country icon Johnny Cash released his final album, the covers-heavy American IV: The Man Comes Around, in November 2002. His wife, June Carter Cash, died six months later—followed four months after by Cash himself. It’s hard to separate the album from its contextual sadness—especially given the LP’s heart-stopping centerpiece, a brooding rendition of Nine Inch Nails’ “Hurt,” in which the iconic singer glimpses his own mortality. “I hurt myself today/ to see if I still feel,” Cash sings over wispy acoustic guitar and piano chords, his ancient baritone quivering in the darkness. “What have I become, my sweetest friend?/ Everyone I know goes away in the end.” Trent Reznor’s dissonant original—recorded for the second NIN album, 1994’s The Downward Spiral—is often interpreted as a suicide note. In Cash’s hands, it’s a death-bed confessional.—Ryan Reed

1. Sufjan Stevens: “Casimir Pulaski Day”

There is one moment in one song in the world that gives me chills every time I hear it. 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. Then he sings about God: “All the glory when he took our place / But he took my shoulders and he shook my face / and he takes and he takes and he takes.” He’s trying to reconcile the generosity of Jesus allowing himself to be sacrificed on the cross with a god who would let a young girl die from leukemia. And the only conclusion is a chorus of angels whose weeping turns into something like joy as a triumphant trumpet kicks in. There are so many details that lead to my inevitable goosebumps: the guilty sexual explorations of teens who’ve been taught the importance of abstinence (“I almost touched your blouse”); the strict and distant father who makes a big display of his grief; the ineffectual laying of hands and praying; the cardinal hitting the window. Because the characters seem so real, so does the sorrow. I feel deeply for the dying girl and the boy who can’t understand the Why of it all—because none of us really can.—Josh Jackson

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