50 Songs That Are Guaranteed to Make You Cry


Strip away the creeping pumpkinspicization of fall, and there’s something somber and inherently melancholy about this time of the year. It’s when the days get shorter, the leaves fall off the trees, the skies are gray, and the air is cold enough to demand scarves and hats. And it’s also the time to huddle up by the open fire, drink tea, and listen to sad music! With that in mind, here’s a playlist inspired by our recent list of heart-wrenching movies — an epic selection of songs guaranteed to make you cry, from the tear-jerkingly forlorn to the moving and beautiful.

Big Star — “Holocaust”

We might as well start with what’s perhaps the bleakest song ever written, hey? This lyric is one of the saddest in rock’s canon, cataloging the slow disintegration of its subject and culminating in the lines, “You’re a wasted face/ You’re a sad-eyed lie/ You’re a holocaust.” The instrumentation — ghostly echoes of slide guitar and a distant piano — only make the whole thing even more distressing.

Amy Winehouse — “Back to Black”

Quite apart from the story of Winehouse herself, this is one of the most emotive songs about the end of a relationship you’ll ever hear. Winehouse’s lover has left her for his ex, and she’s sitting contemplating an empty future: “You go back to her/ And I go back to black.”

Angel Haze — “Cleaning Out My Closet”

The most harrowing song of the last couple of years, bar none.

Lou Reed — “The Kids”

Legend has it that producer Bob Ezrin told his own kids that their mother wasn’t coming home because she’d been killed in a car accident, and then recorded the result to use during the extended instrumental in this song. The story’s probably apocryphal, but the result is heart-wrenching, especially contrasted with Reed’s brutal lyrical treatment of the woman whose kids are being taken away.

Fela Kuti — “Coffin for Head of State”

By far the most upbeat song on this list, so much so that it takes a little while to realize that Fela is excoriating the Nigerian government, singing about religious hypocrisy, corruption, and, most movingly, the raid on his compound in 1977, in which his own mother was killed: “Them steal all the money/ Them kill many students/ Them burn many houses/ Them burn my house too/ Them kill my mama.”

Gowns — “Cherrylee”

Gowns’ one and only album Red State is bleakly brilliant — it’s like Larry Clark’s Tulsa set to music, a portrait of narcotized small-town alienation in the sort of Middle American place that barely registers on the radar of either coast (or Washington, for that matter). This, the album’s final song, finds Erika M. Andersen’s narrator in a final moment of clarity, staring into a mirror and seeing her addictions staring back at her.

Frank Ocean — “Bad Religion”

On the most superficial level, this is about unrequited love, but it’s surely no accident that Ocean uses religion as a metaphor for the love in question, given how hostile the world’s religions in general have been to homosexuality over the millennia. As such, the chorus — “If it brings me to my knees/ It’s a bad religion” — functions both as a lament over a bad relationship and a rejection of the spiritual beliefs with which he was raised, with the “I could never make him love me” just as easily applicable to God as it is to a lover.

Nick Drake — “Saturday Sun”

Nick Drake’s music is just made for autumn, and while his entire discography is perfect for sitting with tea and watching the leaves fall, there’s something particularly emotive about this, the closing track from Five Leaves Left. It’s perhaps because the lyric promises a fleeting levity, with the appearance of the eponymous Saturday sun, but by the end of the song it’s gone again: “Sunday sat in the Saturday sun/ And wept for a day gone by.”

Bruce Springsteen — “The River”

Where even to begin with Springsteen’s finest moment? “Is a dream a lie if it don’t come true/ Or is it something worse?” is perhaps the most succinctly heartbreaking verdict anyone’s ever recorded on a life that hasn’t turned out the way you dreamed it might in your youth. Also, if the extended monologue at the start of this live version doesn’t give you a lump in your throat, well, you’ve got a stony, stony heart.

Leonard Cohen — “Alexandra Leaving”

One of the very best songs of Cohen’s career, which is, of course, high praise indeed. Like many of the songs on this list, it catalogs the end of a relationship, but does so with the sort of wisdom and perspective that comes with age — and it’s all the more emotive for being so.

Bonnie “Prince” Billy — “I See a Darkness”

A song that addresses two topics that are rarely approached by lyricists — depression and male friendship — and does so with both clarity and compassion. The Johnny Cash version is pretty moving, too.

Townes Van Zandt — “Tower Song”

It’s really a case of closing your eyes and pointing at a Townes Van Zandt song here — the great man’s discography is steeped in melancholy. Still, there’s something particularly gorgeous about this song, a forlorn meditation on a love affair that’s failing and appears doomed.

Susana and the Magical Orchestra — “Believer”

This song approaches similar subject matter, and it’s even more starkly beautiful than Van Zandt’s song. The “believer” part of the lyric is open to interpretation — it could be taken as suggesting that the affair is ending because of the participants’ divergent beliefs, or simply because the narrator has stopped believing in the relationship itself.

Nick Cave and the Bad Seeds — “Into My Arms”

It’s not all breakup songs on this list, mind you (otherwise your correspondent would have long since dissolved into a puddle of existential angst). This is the most delicately beautiful of love songs, starting with the remarkable declaration “I don’t believe in an interventionist god,” and containing some of the most poetic declarations of love you’ll ever hear.

Mark Lanegan Band — “Strange Religion”

Bubblegum is a dark record, dealing with Lanegan’s addictions and his difficult history, but this song is all the more moving for its bruised optimism. It’s the story of two burnouts who find something to love in one another, and it’s utterly convincing.

The Devastations — “Previous Crimes”

While we’re on bruised love songs, this is the standout track from The Devastations’ first album, and one of the most beautiful ballads of the last decade or so. It’s a song that is world-weary and hard-bitten, its narrator having long since lost the starry-eyed romanticism that characterizes more saccharine love songs — “I do not believe, believe in forgiveness/ Or setting suns” — but still somehow retains a fragile faith in the idea of love itself. Ultimately, its plea is simple and plaintive: “I want to live with you/ I want you to stay here with me/ In my loving arms.”

Portishead — “Roads”

The most stark and forlorn moment in a discography that hasn’t exactly been characterized by levity, this track finds Beth Gibbons confronting a cold winter morning with no one for company. She’s never sounded more lonesome or mournful than she does when she sings, “I got nobody on my side/ And surely that ain’t right…”

Radar Bros. — “Supermarket Pharmacy”

Jim Putnam’s entire career has been an exercise in perfecting a certain beautiful, melodic melancholy, but for all that his later albums have been more accessible and better produced, some of his most effective and moving songwriting came on Radar Bros’ self-titled debut. This lyric is a portrait of someone lost in the modern world, both plaintive and somehow sinister, especially the image of being “In the shower, with the scrubber/ The crimson goes away.”

Blur — “No Distance Left to Run”

If you’ve ever come to the sad end of a relationship, well, you’ll be able to relate to this. And if not, it might just elicit a couple of sympathetic tears anyway.

Sparklehorse — “Sad and Beautiful World”

This was heartbreaking enough before its author committed suicide. Now? Dear god.

Casiotone for the Painfully Alone — “Natural Light”

Vs. Children is a pretty bleak album all round, a series of meditations on childbearing and broken families built around a loose narrative about a protagonist who periodically leaves his partner to go and rob banks, but this song takes the cake — it depicts the narrator years later, staring at an old, yellowing picture, wondering what might have been: “I thought on things that we said/ What if we’d had the kid?/ I guess he’d be 15.” (Mark Kozelek’s version is similarly heartbreaking.)

Jens Lekman — “Every Little Hair Knows Your Name”

Also on the breakup front, this final song from I Know What Love Isn’t finds Lekman looking back on the breakup to which the album is devoted. The song is leavened with Lekman’s usual wry humor — “I started working out when we broke up/ I can do one hundred pushups/ Could probably do two if I was bored” — but it’s genuinely moving, too.

Aaron Freeman — “Gener’s Gone”

This is the former Gene Ween’s farewell to his alter ego, and considering how much his former band’s career revolved around their signature oddball humor, it’s a surprisingly moving and tender piece of work: “Gener’s gone,” he sings over a quiet accompaniment of piano and acoustic guitar, “He loved you all just like his children/ And it broke his heart to say goodbye.” It’s even more somber when you read the accompanying text on Bandcamp: “After 20+ years of near-fatal drug & alcohol abuse (thankfully culminating with intensive but successful rehab), AARON FREEMAN (aka Gene Ween) was left in a dire financial situation. All proceeds [from the sales of this recording] will go directly to Aaron, as he continues down the path toward creative freedom and personal health.”

John Cale — “Amsterdam”

One of the most chastening realizations about love is that contrary to what cultural mythology (and The Beatles) would have you believe, love isn’t all you need — sometimes it’s not enough for two people to love one another. This song finds Cale cutting loose a lover after they’ve both come to this realization: “She says she fell in love with men who knew the way to treat a lady/ Her life has settled for the best of things/ That I couldn’t give her/ And it’s not her fault, she’s not the one to blame…”

Cat Power — “Good Woman”

On a similar note, this is a song about a relationship in which both parties clearly love each other dearly, but that for whatever reason simply can’t work — the song doesn’t specify one in particular, which makes it all the more relatable. The entire second verse, in particular, is just devastating: “I don’t want be a bad woman/ And I can’t stand to see you be a bad man/ I will miss your heart so tender/ And I will love this love forever/ And this is why I am leaving/ And this is why I can’t see you no more/ And this is why I am lying when I say/ That I don’t love you no more.” ARGH.

Regina Spektor — “Summer in the City”

Spektor’s determined quirkiness can be irritating at times, but when she leaves them behind to just be emotionally honest, the results are great. This is about loneliness, pure and simple, and missing a lover who’s departed — something that’s made all the worse by seeing a bazillion other beautiful women on the street in the sun.

PJ Harvey — “A Perfect Day, Elise”

It’s often interpreted as a murder ballad, the story of a man killing a woman who won’t return his love, but “A Perfect Day, Elise” is more nuanced than that — there’s an alternate interpretation that in pulling the trigger, the song’s protagonist is killing not a woman but himself. The fact that it’s apparently inspired by JD Salinger’s “A Perfect Day for a Bananafish” seems to support this reading, but the song’s ambiguous enough to work with either interpretation — and either way, it’s a heavy piece of work.

Arcade Fire — “In the Backseat”

From when Arcade Fire’s songs were genuinely emotive, albeit still somewhat over-dramatic, and didn’t require formal dress to enjoy. But the lyric here is great, working around a clever metaphor that equates adulthood with learning to drive, and conjuring the desire to go back to a time when you could just sit in the back seat and watch the countryside go by, free of all care and responsibility. The fact that the song is about the death of Regine Chassagne’s grandmother makes it all the more dramatic.

Suede — “The Living Dead”

The dark side of Suede’s ceaseless hedonism: the story of a couple whose heroin addiction has reached the stage where there’s nothing that can be done for them. At the time, Brett Anderson explained that the song was about two friends who had since died.

The Beach Boys — “God Only Knows”

The prettiest declaration of ambivalent, melancholy love that the last half century or so has to offer. Those vocal harmonies!

Eels — “Elizabeth on the Bathroom Floor”

Listening to Electro-Shock Blues from start to finish is the sort of thing that can catalyze a full-fledged weep-athon if you’re feeling fragile; the album deals with the suicide of Mark Everett’s sister and his mother’s death from cancer. This song relates to the former, and specifically a previous, failed, suicide attempt — the lyric is apparently taken from one of her diary entries. Quite what sort of emotional toll it must have taken for Everett to sing this song from her point of view doesn’t really bear thinking about.

The Antlers — “Epilogue”

The Antlers’ Hospice is another album that explores death, via the story of a caregiver in a cancer ward and his relationship with a patient who has terminal bone cancer. It’s about as much fun as it sounds, to be honest, but it’s also beautiful and moving. As the title suggests, this song discusses the inevitable end: “You’re screaming and cursing/ And angry and hurting me/ And then smiling and crying/ Apologizing…”

The Cure — “Pictures of You”

Disintegration is a strong contender for the title of World’s Most Depressing Album, and this is its epic centerpiece: five-and-a-half tear-jerking minutes that find Robert Smith looking at pictures of his lost love, because now pictures are all he has left.

Art Garfunkel — “Bright Eyes”

From the soundtrack to Watership Down, and surely the saddest song ever to catalog the death of a rabbit. It was written by songwriter Mike Batt, and its lyrics apparently drew on the death of his father from cancer. There have been many versions over the years, but Garfunkel’s is probably the best known.

Jacques Brel — “Ne Me Quitte Pas”

The title translates as “Don’t Leave Me,” but honestly, you don’t need a word of French to appreciate this song’s air of desperate despair.

Terry Jacks — “Seasons in the Sun”

Also on the Jacques Brel front, this song is an English adaptation of his lyric “Le Moribond,” and depending on your interpretation, it’s either about suicide or death from illness (the title of Brel’s original would seem to suggest the latter). Either way, it finds the protagonist bidding farewell to his loved ones with heartbreaking clarity.

Bille Holiday — “Strange Fruit”

Perhaps the most powerful protest song of them all, Holiday’s anti-racism song is as subtly dramatic as it was 70 years ago. And it’s still pretty much just as relevant, sadly.

Radiohead — “No Surprises”


DMX — “Slippin'”

It’s easy to ridicule DMX, or to excoriate him because of his cruelty to animals. All this is entirely justified, but he’s a pretty sad case, a man whose career and life have been ruined by drugs and alcohol — and knowing his history in the 15 years after this song’s release means it’s pretty poignant and depressing listening, especially its declaration that “Now I know that happy days are not far away” and its promise that “Something’s gotta give, gotsa change because now I got a son/ I gotta do the right thing for shorty/ And that means no more getting high, drinking 40s.” Sadly, it wasn’t to be.

Elliott Smith — “Twilight”

Another artist where you’re not exactly short of choices, but still, it’s hard to go past this plaintive ballad off From a Basement on a Hill. There’s plenty of debate among fans about whether the “somebody” referenced in this song is an allusion to Smith’s addictions, but either way, there’s something particularly bleak about the way that Smith sings “I’m tired of being down/ I got no fight.” It’s the way this song floats a possibility of something better, and then snatches it away, that makes it so moving.

Manic Street Preachers — “4st 7lb”

Perhaps the most harrowing depiction of eating disorders ever committed to tape, and all the more disconcerting for its lucidity and self-awareness. The imagery is alternately confronting (“My hands are trembling stalks/ And I can feel my breasts are sinking”) and curiously beautiful (“I want to walk in the snow/ And not leave a footprint”), while the music moves from atonal distortion into a reflective, elegiac coda that seems to find the protagonist floating into death.

The Carpenters — “Rainy Days and Mondays”

Oh, Karen.

The Drones — “Locust”

Gareth Liddiard’s never really spoken about how autobiographical this song may or may not be, but several of his lyrics appear to reference an ex-girlfriend who committed suicide, and this song deals with his history in stark, moving detail. “Locust” conjures the bleak isolation of Liddiard’s hometown, Port Hedland, and some of the imagery is stunning: “They built a prison, let it temper in the sun/ It rose up off the plateau like the last tooth in a gum.” And the last verse, good grief: “My first girl’s old man was in a later war/ He drank like a motherfucker, now I know what for/ She took my van, put louie in the jack/ She left a suicide note, and I got him to thank for that.”

Sia — “Breathe Me”

Happily, the Six Feet Under soundtrack brought this to prominence, because it’s Sia’s best song, a portrayal of self-mutilation and depression, and a small, quiet request for… not help, exactly, but just friendship and comfort. Sometimes, that’s all a friend can offer, and sometimes it’s enough.

Kanye West — “Hey Mama”

A heartfelt tribute to West’s beloved mother, after whom his creative agency and lecture series are named. It’s West at his most unabashedly sentimental, and it’s really lovely.

The Flaming Lips — “Do You Realize??”

Look, Wayne Coyne seems to have devoted most of the ’00s to his pursuit of unrepentant and ongoing douchedom, but Yoshimi Battles the Pink Robots was a wonderful album, and this song — a meditation on the transience of love and life, and the importance of making every moment count — is one of the most profound lyrics to ever grace a pop song. Everyone will die, and everything will pass, but life can also be beautiful. Embrace it, and when it’s done, let it go.

Mazzy Star — “Blue Light”

Unlike most of the songs on the list, the meaning of this song remains somewhat elusive, but that doesn’t make its general air of melancholy any less compelling. The blue light here has always evoked Gatsby’s green light for me, but the song’s lyric is loose enough that listeners are invited to find their own interpretations. And again, Mazzy Star are just made for autumn.

Spiritualized — “Oh Baby”

A fractured lullaby for Jason Pierce’s daughter. It starts as a gentle appeal to take all that life has to offer, building to a crescendo as instrumentation comes crashing in and Pierce’s voice cracks as he sings, “Baby, I can’t tell you any more than I know/So darling, reach out and take it all in as you go…”

David Bowie — “‘Heroes'”

Bowie’s lyrics are often oblique enough to defy the sort of direct emotional impact that characterizes most of the songs on this list — but there’s nothing oblique about the tragic, doomed romanticism of “Heroes.”

Johnny Cash — “Hurt”

Yes, it’s almost gotten to the stage where this can rival Jeff Buckley’s version of “Hallelujah” as Song Most Abused to Indicate “Meaningful” Moments and REAL EMOTION. But come on, it’s also pretty damn sad, too, especially that video.