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

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The 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. They’re filled with heartbreak, untimely death, rejection and despair. We hope you enjoy.

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. Father John Misty: “The Palace”
Throughout the last half-decade or so, Josh Tillman blurred the line between himself and his Father John Misty character, routinely shrouding his real experiences and emotions behind outlandish stories and batshit crazy interviews. But that line becomes erased completely on God’s Favorite Customer, which sees him tell a highly autobiographical tale of heartbreak and depression concerning his marital discord, leading him to a few-month stay at an unnamed hotel. The album’s emotional core is the crushing ballad, “The Palace,” where Tillman removes all bells and whistles for a straightforward track about his yearning, yet inability to go home. “I’m in over my head,” he repeats over a glacially slow minor piano chord just after admitting that he wants to fix things—“Last night I texted your iPhone/ And said I think I’m ready to come home.” He finally reunites with his partner by the end of the album, but at this point in God’s Favorite Customer, that happy ending is thrown completely in doubt, buried underneath a bag of speed and a tray of dirty room-service dishes. —Steven Edelstone

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. Deer Tick: “Christ Jesus”
Deer Tick lead singer John McCauley has always had a rough voice, the kind of well-worn one where you know he’s seen some shit. But throughout his band’s decade-plus-long career, his voice was always confident, hitting every note… until the closing seconds of “Christ Jesus,” the reworked piano-driven album closer on The Black Dirt Sessions (an earlier electric guitar version appeared on 2007’s War Elephant). McCauley lets out a final scream, one where you can hear all of the anguish and distress that he’s built up for years of believing in Jesus, only for it to give out at the last second. That torment we hear is the result of the a single moment where McCauley finally loses faith in the God he grew up believing in, realizing that he will never return or offer any relief to his suffering. “Christ Jesus/ As I’m drowning/ And I struggle to breathe/ It’s your face I don’t see,” he screeches out in his beaten and scratchy voice over a distant and mournful piano and occasional cello line that never offers any sort of respite for what’s ailing him. —Steven Edelstone

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. Ryan Adams: “Dear Chicago”
This whole list could be Ryan Adams songs—he has a knack for turbulent interpersonal relationships, which he tends to process with one sad-bastard tune after another. “Dear Chicago” is one of his best. The tune consists of Adams’ voice, a pair of acoustic guitars and just enough reverb to give the song a late-night, empty-room feel. There’s no verse-chorus structure here, just a tumble of lyrics that read like an unexpected update from an ex offering more details than are entirely comfortable to know. Though there’s a playful aspect to the song—referring to the people he’s talking about by city names—Adams sounds lonely and at least a bit regretful, even if you get the feeling he would have a hard time explaining why. “Dear Chicago” came out in 2002 on Demolition, which is itself a sad story: the album consists of songs Adams had written for other three or four other albums that remain unreleased. —Eric R. Danton

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” (2001)
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. Frank Ocean: “Ivy”
“I thought that I was dreaming when you said you loved me.” The opening line to Frank Ocean’s “Ivy” seems like a romantic line on first glance—until you realize love is in past tense, quickly giving way to the next line, “the start of nothing.” Over a plucky electric guitar line, Ocean proceeds to discuss his recently ended relationship in extreme detail, from being friends through their public display of affection, remembering when his partner put their arm around his shoulder in a hotel. But what hurts Frank the most (and all of us following a tough breakup) is his ex’s ability to bounce back so quickly—“I broke your heart last week/ You’ll probably feel better by the weekend. Frank and his ex “ain’t a kid no more,” but it doesn’t make rebounding from heartbreak any easier. —Steven Edelstone

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. Delta Spirit – “Vivian”

Matt Vasquez wrote this History From Below tearjerker as an ode to his late grandparents, who both passed away within a short timeframe. 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. If your heart is made of stone and that’s not enough to choke you up, he also visits his ailing wife from beyond the grave to comfort her as she dies: “I know it’s hard to deal with the pain/you’re yellow from your liver giving out/so just close your eyes and think of me/oh, Jerry’s not leaving this gal.” I’m getting misty just thinking about it.—Bonnie Stiernberg

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

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