24 signature sad songs of the past 20 years

Atmosfolk trio Daughter kicked off the walk-up to their January 2016-anticipated album with "Doing The Right Thing," a tale of slipping away into Alzheimer's ether. The tune was inspired by lead singer Elena Tonra reflecting on her own grandmother's struggle and Tonra's ensuing reflection on how its affected her mother. "I'm just fearing one day soon, I'll lose my mind / Then I'll lose my children / Then I'll lose my love / Then I'll sit in silence" she sings, speaking from the pespective of an aging mind. It's heavy, and so vivid it was never anything but real.  

Of course, Daughter isn’t the only maestro of musical misery: For your tear-stained enjoyment, we’ve gathered 23 others (listen along on Spotify here!) of the best sad songs of the past 20 years. So grab your earbuds—and a thick pack of tissues—and weep with us. —Madison Vain

P.S. If you feel like we missed your favorite sad song, let us know in the comments!

Sufjan knows how to craft the perfect sad song: Just listen to his haunting tale of serial killer “John Wayne Gacy, Jr.,” or my favorite funeral song from The O.C. (R.I.P. Johnny!), “For The Widows in Paradise, For The Fatherless in Ypsilanti.” But on his latest album, Carrie & Lowell, the indie-folk darling has outdone himself. On the utterly devastating “Should Have Known Better,” he reminisces about the time his mentally ill mother left her children at a video store, when he was “three, maybe four.”

The simplest things hurt the most, don't they? Or maybe they're just the most honest. Either way, Adele's "Take It All" off her sophomore album 21, is both. It's a girl, pleading for a guy to tell her where she went wrong. What step did I miss? I can change, I swear! She's given every ounce—her love, her heart, her time, everything—to a man who can't see it. This is her white-knuckled grip on the fraying edges of their relationship. Put as simply as the track itself, it hurts.—Madison Vain 

Rihanna might be famous for her more dance-ready, beat-heavy tracks, but “Stay” shows the Barbadian singer is completely capable of carrying an emotional piano ballad. With simple lyrics like “I want you to stay” and guest vocals by Mikky Ekko, “Stay” succeeds as a raw, heart wrenching break-up song about losing someone you really wish would, well, you know.—Ariana Bacle

On the schmaltzy standout track from 2012’s Channel Orange, Frank makes like his namesake and leaves us in an ocean of sadness. (But seriously.) When his voice strains on the word “knees” (“If it brings me to my knees / It’s a bad religion”), you feel it in your gut. The song is especially potent when you remember that it came out shortly after Frank himself did, writing a soul-baring Tumblr note about falling in love with a man. —Isabella Biedenharn

Hearing "I hurt myself today, to see if I still feel / I focus on the pain, the only thing that's real" in the country great's deteriorating warble—Cash recorded "Hurt" a year before his death—moves this Nine Inch Nails cover from an already sad song about heroin abuse to an almost unbearable tune by an artist woefully looking back. Cash turns it into a perfect, alarmingly tender dirge.—Madison Vain 

Something big is about to break open, to let the mad rush of a disintegrating relationship pour out—but there isn't any of that bombast left by the time we get to "Say Something." It's a resigned song, save for that stray sliver of hope woven between delicate piano chords—hope that she'll say something, anything to pull him back in, and prove that she cares. (Such is life: She doesn't.) —Madison Vain  

It's hard to feel for the "other woman"—the woman who refuses to accept that the man she loves is never going to break up with her, that she's waiting around on the edges of his life for a day that will never come. But certainly we've all wanted something we can't have. And good God, when Jennifer Nettles breaks over the lyric "I've given you my best / Why does she get the best of you?" there's nothing to keep your heart from plummeting to the pit of your stomach. It is, simply, the purest, on-my-knees-begging heartache I've ever heard. —Madison Vain 

The first two notes of "Come Home" incite memories of Mötley Crüe's abode-centric "Home Sweet Home." But the tone, intensity, and instrumentation immediately veer off toward somber longing. Ryan Tedder pleads for his lover's return. As the song tails off, his implicit failure—she's not coming back—sets off mourning that's greater than what comes when it's too late to apologize. This is the sadder, realer build-up to that moment. —Will Robinson

"Missing You" is a song from a different time, composed for a movie featuring a pair of icons (Khan, Knight) and two then-upstarts (Brandy, Tamia). It stays in line with the plot of Set It Off, in which three of the four leads die. Even if you don't know the context, the music makes you confront a universal fear: losing your best friends.—Will Robinson

They’re the snot-nosed brats who wrote about mom-dude fellatio and made Green Day look mature. But maybe it’s that aversion to seriousness—and the band’s rabid fan base—that made “Adam’s Song” so poignant. The track tackles the alienation bassist-singer Mark Hoppus felt while the band was on its longest tour to date, but it also address themes of suicide, dying alone, and lost glory. Hoppus sang the Nirvana-quoting lyrics—the song slightly updates a verse from “Come As You Are”—in a single take. It’s not the coolest blink song, but it is the most profound. —Eric Renner Brown

There is no lonesomeness in music that compares to the lonesomeness in country—and the boy in the Bruce Robinson-penned "Travelin' Soldier," two days past 18 and off for the Vietnam War, is lonesome. That is, until a kind girl his age accepts his desperate plea to be his "someone" once he's gone—where he'll send letters, who he'll keep as his tether to the land of the living. His last note says things are getting rough and he might not be able to write for a while, and then the song jumps to the girl's high school announcing the list of local Vietnam-dead at the football game. His name is called and she's the only one who recognizes it. She mourns him, by herself, under the bleachers. Lonesome, all over again.—Madison Vain

Eminem, who produced this posthumous Shakur cut, used a sample of John's "Indian Sunset" to highlight 'Pac's anti-violence rhetoric. It's a final plea to bring peace to the streets, one released eight years after the rapper died in a drive-by shooting. While we'd gladly exchange its resonance for more years with the rapper himself, his unfinished mission and the eerie context only strengthens the song's mourning. It's simultaneously universal and unique.—Will Robinson

Tidal was Fiona Apple's introduction to the world. "Criminal" and "Shadowboxer" were the chart-climbers. But "Never Is a Promise" occupies a special place in her anthology. Apple wants one thing—for her lover to mean what he says. And she begs desperately, over minimal production, for an assurance that what she hears is true. The ultimate lack of resolution is striking. —Will Robinson

An even more unsettling posthumous release than "Ghetto Gospel," "A Fond Farewell" appears on Smith's From a Basement on the Hill, released almost exactly a year after the singer's death. It's ironically cheerful, with lyrics channeling a melancholy resignation to the powers that be. Smith's reported drug abuse and the questionable circumstances of his death make this a hard, but cathartic listen: Smith sings the pain for you.—Will Robinson

It's the kind of emotional song that you physically can’t listen to, but need to listen to hear at the same time. Even before knowing it's about the AIDS epidemic, the upbeat-yet-sorrowful melody will hook you. And as if the song (and Rent) weren’t sad enough, Glee covered it in honor of Cory Monteith’s death for the show's tribute episode. —Isabella Biedenharn

Ben Folds chronicles one of the more unpleasant days-after-Christmas in “Brick,” a ballad about taking his girlfriend to get an abortion. The track captures both the anticipation and the aftermath with a clear narrative, describing their drive to the doctor and their post-procedure breakdowns. Although the instrumentation’s pretty, Folds’ voice isn’t always—giving “Brick” a dose of unfiltered sorrow that makes his account of the situation all the more powerful.—Ariana Bacle

The short answer: On “Don’t Look Back In Anger,” Oasis made good on their promise of becoming the New Beatles, channeling all the Fab Four’s heartbreak and beauty through the lens of Nineties Brit-pop. The long answer: The Brothers Gallagher are about as arrogant as rockstars come, and “Don’t Look Back In Anger” brilliantly denies culpability. But that’s where the beauty lies. Enough sad songs wallow in confusion and depression—”Don’t Look Back In Anger” holds a magnifying glass to reckoning and its deceptions. The guitar solo ain’t too bad, either. —Eric Renner Brown

"This is the deep and dying breath of this love that we've been working on"—those final moments just before someone's willing to just come out and say, "We're over. This can't be saved." If "the blues is the truth," as Jack White says, John Mayer is singing some of the saddest blues on "Slow Dancing in a Burning Room." —Madison Vain

Beck may now be synonymous with mope-folk, but when he dropped 2002’s Sea Change, he was alt-rock’s resident weirdo, riding the success of freak anthems “Loser” and “Where It’s At.” Melancholy and quiet, Sea Change—inspired by Beck’s disintegrated engagement—showed listeners his tender side. Underscored by glockenspiel and a drifting acoustic melody, “Lost Cause” exposes Beck’s somber voice and devastating lyrics, which articulate the numb defeatism we often feel in our bleakest moments. What’s that about two turntables and a microphone? —Eric Renner Brown

A good sad song doesn't need a book's worth of lyrics to give it emotion—and M83's "Wait," an atmospheric, bare track, proves that. Although it features some string builds that hint at optimism, the overall mood of "Wait" is epic, epic melancholy made for long, thoughtful drives (and for teen romances—the song was featured twice in The Fault in Our Stars).—Ariana Bacle

Despite its complicated title, “Transatlanticism” is perfect in its simplicity: namely, that repeated lyric, “I need you so much closer,” and those long, howling notes (“Come oooooooon, come ooooooon”). This song, in all its emo glory, is the perfect soundtrack for the moments when you feel like a character on a teen soap—the high of a first kiss and the plummet of a first heartbreak, when all you can do is cry into your diary. Ben Gibbard really knows his stuff. —Isabella Biedenharn

Initially, the faint drums, ethereal keyboards, and arpeggiated Tarantino guitars hang like the still air before a summer thunderstorm. On “Your Love Is Killing Me,” that storm is Sharon Van Etten’s voice, simultaneously tender and depraved, channeling—because singing this emotional isn’t really singing—lyrics that vividly illustrate romantic codependency. The bleakness stems from our magnetic attraction to heartbreak, the tendency to repeat mistakes in the absence of established barriers. “Cut my tongue so I can't talk to you / Burn my skin so I can't feel you / Stab my eyes so I can't see," goes a song so good you can’t turn away.—Eric Renner Brown

Isaac Brock wheezes that the world is a fallen, irrevocably broken place on "Bankrupt on Selling." It's as big as the apostles being willing to sell off their savior, and as small as the breakup of an individual relationship—lost as one partner succumbs to addiction and the other to pessimism. Right in between is the twice-repeated lyric, "all the people you knew were the actors." It's all f----ed, basically. —Madison Vain