20 Sad Songs: A Pigeons & Planes Playlist

There are few other active songwriters who put their emotions to music like Fiona Apple. We could have legitimately included more than half her discography on here, but it seemed unfair to the competition.

Because when she sits down at the piano and opens up her heart, Fiona unlocks a vulnerability that strikes you to the core. It can be a bit bewildering, as she's also an exquisite songwriter. Her chord progressions are never boring or predictable, and her lyrics always follow a narrative thread that, more often than not, leads you straight to a pool of tears.

"Never Is A Promise" was written when Fiona was 16, penned after the boy who had taken her virginity left Fiona for another. It remained virtually unchanged from its demo form to the final master, and was released as the incredible Tidal's last single.—Graham Corrigan

On the surface, "Back to Black" is a sad break-up song. It's a case of unrequited love: Amy Winehouse is deeply in love with her object of affection, but the one whom she loves goes back to his old lover. Mark Ronson and Salaam Remi's production pairs perfectly with Amy's mournful vocals, and the lyrics are completely relatable. "Back to Black" goes much deeper than another break-up song, though.

Yes, every songwriter is generally inspired by his or her own life. But the influence for this miserable song was none other than Amy's eventual husband, Blake Fielder-Civil, who ended their tumultuous relationship to be with his ex-girlfriend. This break-up would lead to the creation of Winehouse's most celebrated album.

The height of her career, though, was marred by drugs and controversy, and the recent documentary on the singer gone too soon, Amy, gives further insight into just how Blake's influence may have led to her demise. Give "Black to Back" a listen with that in mind—Amy, mourning over a relationship with someone who was simply no good for her—and try not to be moved by the hopelessness of this song.—Joyce

Matt Berninger's voice has the sort of rumbling, discomfiting quality that makes it sound like he'd rather not be sharing the intimacies that play out in The National's music. It works with their brand of down-tempo rock, especially when they get sorrowful. "Sorrow" finds the band in glowing, apathetic misery—the song seems stuck in time, and they once literalized that feeling by playing "Sorrow" for six hours straight as part of a performance.—Graham Corrigan

A lot of the saddest songs are intimate affairs, and lyrically, Lykke Li's "Never Gonna Love Again" is just that. But sonically, this is a sweeping, dramatic ballad that turns sadness and hopelessness into an enormous, engrossing emotion—something it often is.—Confusion

"Dry Your Eyes," from The Streets' second album A Grand Don't Come For Free, is the saddest song in Mike Skinner's catalog of incredibly open and emotionally honest songs. It's a study of one man trying to cope with his girlfriend breaking up with him, but it's the the incredible detail Skinner goes into describing the scene that makes this song so powerful.

With a painter's eye, Skinner details small things like the narrator's shaking hands and his panicked fight against the inevitable: "Tryin’ to pull her close out of bare desperation / Put my arms around her tryin’ to change what she’s sayin’."

This bitingly honest half-spoken, half-sung portrait of a broken man was also The Streets' most succesful single, reaching number one in the UK charts the week it was released.—Constant Gardner

With Christmas looming, Joni Mitchell's "River" is perhaps the most appropriate song for anyone wishing their situation was different. If you're stuck around joyous celebrations this year, just wanting to get away from it all, this is your soundtrack.—Confusion

Look, we could have included a lot of Elliott Smith songs on this list, but "The Biggest Lie," the last song off his 1995 self-titled album, is one of the most heartbreaking. Smith's tragic death only amplifies the hopeless, broken tone that he sings with, and listening to lyrics like, "Everything you do makes me wanna die" is chilling.—Confusion

A classic song from a true legend. Leonard Cohen's gruff vocals and spare arrangements mean a number of his songs could have appeared on this list, but "Hey That's No Way to Say Goodbye," from his debut album Songs of Leonard Cohen, is one of his best. Cohen's past as a poet and novelist is clear as he sets up the sadness to come with, "I loved you in the morning, our kisses deep and warm, your hair upon the pillow like a sleepy golden storm."

Alas, all will not be well for long, and the simplicity and directness of saying, "Hey, that's no way to say goodbye," contrasts perfectly with the imagery used throughout the rest of the song. He isn't screaming and shouting as his lover leaves, but the acceptance in his voice is part of this song's power and innate sadness.—Constant Gardner

"Bad Religion" is the climax of Frank Ocean's channel ORANGE, powerful in both production and delivery, and it's the one song that had everyone talking due to his choice of pronoun. Relating back to its title, "Bad Religion" begins with the organs. A makeshift confessional is created in the back of a taxi as Frank shares his pain with the driver. It's unrequited love again, a common thread throughout this list of sad songs.

"Bad Religion," though, is layers upon layers of Frank Ocean's struggles: of being in love with a man who doesn't love him back, of intolerance of homosexuality in religious communities, of worshipping someone on the level of God but of that leading to complete and utter heartbreak—conveyed in the most incredibly moving way. Its emotion hits you right in the gut, but that's why we love Frank Ocean, right?—Joyce

Hospice, The Antlers' third album, tells the story of a relationship between a hospice worker and a female patient suffering from terminal bone cancer. If the backstory alone isn't enough, Peter Silberman's vocals, delicate, tremulous, and often defeated, will have you leaning in to hear exactly what he's saying.

But when you listen closely to "Kettering," or listen to this album in full, it's almost impossible not to leave emotionally drained. "Kettering" starts gently, soft piano accompanying Silberman's description of the hospital bed and patient in it, but after his incredible final lyrics, "You made me sleep all uneven, and I didn't believe them when they told me that there was no saving you," the song bursts into driving, anthemic rock territory, an appropriately tumultuous sound to match the waves of emotion crashing down on the listener.—Constant Gardner

Sufjan Stevens can do it all. Besides his mastery of Earth's physical instruments, Stevens is able to write songs for every mood, from the soaring heights of "Chicago" to the bittersweet sadness of "For The Widows in Paradise, For the Fatherless in Ypsilanti."

A banjo has never sounded so sad—Sufjan himself has said the song comes from a (fictional) place of loss. He once contextualized the song onstage: “Let me do a song really quick about a small town up here called Paradise. Michigan has Paradise as well as Hell, Michigan. It’s kind of interesting. Paradise is a place…I noticed when we went up there to play a football tournament in high school, I noticed that there was all these single mothers and women and grandmothers but there weren’t any men, and so I had sort of devised a story in my mind that they had all died in the war and that they were all widows."—Graham Corrigan

When Jeff Buckley passed away (under mysterious circumstances), the mournful beauty of his "Hallelujah" cover became the singer's biggest posthumous hit. Maybe it's the way he left us, or the fact that "Hallelujah" shows you the full range of Buckley's incredible voice, but the song has grown in legend to the point where it may be as popular as Leonard Cohen's original and John Cale's cover.

But where Cohen's drowsy drawl leaves you somewhere morose, Buckley's vocals are full of a hope he never got to see through. With its backstory on tow, "Hallelujah" becomes a song about personal loss in conjunction with the religious stories it tells.—Graham Corrigan

As we got to know Conor Oberst in the late '90s and early 2000s, he was unabashed about his sadness, and through that, he created some of the most moving—and most depressing—songs around. "Something Vague" is peak Bright Eyes, making that sense of hopelessness all the more visceral. The lyrics, "You see your breath in the air as you'll climb up the stairs / To that coffin you call your apartment [...] And you're not really sure what you're doing this for / But you need something to fill up the days," are more than relatable; they are daily thoughts for some of us.

But then comes Oberst's confession of darker thoughts, sung with the utmost exasperation in a crescendo as his voice is cracking. He's tired of life, and while these thoughts about standing on a bridge that eventually disappear are worrisome, he touches on them in the most casual way. Conor Oberst submits to his despondency towards this hopeless life. It's just a vague feeling, he concludes, and there's nothing that he can do about it.—Joyce

Back in Radiohead's Pablo Honey days, they were still finding their sea legs, and still thought they were just a rock band. While it might not have produced the best music in their discography, it certainly wasn't a waste of time.

"Thinking About You" is a classic breakup song, deceptively uptempo guitar masking some real hurt: "Been thinking about you," Thom sings, "Your records are here, your eyes are on my wall, your teeth are over there. But I'm still no one, and you're now a star. What do you care?"—Graham Corrigan

Bon Iver’s debut album For Emma, Forever Ago is a storied album. It’s the stuff of legend—this guy went through a painful break-up and isolated himself in a cabin in the woods. While there, by himself, he recorded an entire album of demos, meant to be finished and mastered later.

But as he shared the songs, they started connecting so strongly with others that he decided to put out the album in the state it was in. It remains a sad music masterpiece. This is “Flume."—Confusion

Keaton Henson has an interesting story. When "You Don't Know How Lucky You Are" came out in 2011, the London-based songwriter, illustrator and poet was a highly reclusive character who made music as a personal therapy and had no plans to perform.

Rather than using overwrought, metaphor filled lyrics, Keaton describes his feelings of lost-love and anxiety in a painfully honest way, as if he is just telling us exactly how he feels and recording it. On “You Don’t Know How Lucky You Are” this takes the form of a series of questions presumably being asked to his ex about her new boyfriend, and the results are mesmerizing. Depressing, but mesmerizing.—Constant Gardner

A lot of music glorifies drug use, but The Verve's 1997 song "The Drugs Don't Work" is a more honest depiction of the reality that often comes with drug use: "The drugs don't work, they just make me worse." Lead singer and writer Richard Ashcroft said of the song, "That’s how I’m feeling at the moment. They make me worse, man. But I still take ’em. Out of boredom and frustration you turn to something else to escape."—Confusion

"Something in the Way," like many songs that Kurt Cobain penned, comes from a painful place. It's a somber, gentle staple of their humongous album Nevermind, and one of the tracks they brought to life during their epic MTV Unplugged show, which has been a melancholy memoir for those who were deeply affected by Cobain's suicide.

The actual lyrics, though? For a while, it was assumed that Kurt wrote this track during a period where he was homeless, living under a bridge (although he was more than likely couch-hopping during this period of time). Regardless of the circumstances, this track—be it the darker undertone of the lyrics or the stark contrast to the "sound" that Nirvana encompassed—captures a loneliness, a depressed state where a few key phrases say so much more than a soliloquy ever could. It was the genius of Kurt, and a truly moving piece of sad excellence.—khal

In Nine Inch Nails' hands, the 1994 single from their album The Downward Spiral is a stereotypical appeal to the darker, goth-tinged masses; something you'd expect from them. Stripped bare to the iconic voice of Johnny Cash and an acoustic guitar? It takes the raw, self-inflicted abuse and flips it on its head.

The video was the kicker, which featured a withered Cash shedding real tears over his empire of dirt. It's such a moving, emotional rendition of a track that Trent Reznor said he wrote "as a way of staying sane, about a bleak and desperate place I was in."

When you realize that Cash actually passed away some seven months after the video was shot, it's almost a painful reflection of a life lived long and hard, bundling that emotion and pain into one gritty expression of, well, hurt.—khal

Perfume Genius' Mike Hadreas described "Rusty Chains" as “a song for a man whose lover has died. He remembers a time, before his partner took sick, where everything felt safe and endless. He asks to be taken next, so they can be together again.”

If you're familiar with the band's music, you'll know this subject matter is the perfect, albeit heartbreaking, setting for Hadreas' fragile, sweeping vocals. His heart is laid bare here, and it works beautifully.—Graham Corrigan

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