25 Sad Songs That Will Make You Cry

Frightened Rabbit's low-simmering love song is about looking for love in all the wrong places. Actually, it's mostly about loveless sex as a way of combating inner turmoil and boredom. "You won't find love in a hole / It takes more than f---ing someone to keep yourself warm," head Rabbit Scott Hutchison sings, quivering under the pressure of the hopeless bed-hopping that got his protagonist in such a sad, sorry state in the first place.

So this is what growing up leads to? Post-college idealism turns into a hollowed-out life in Modest Mouse's low-fi account of the American Dream giving way to settling for mediocrity. There are parts about the selling of souls and losing friends here. But the devastating last line is the clincher: "I still love her / Loved her more when she used to be sober and I was kinder." Welcome to the rest of your life, kids.

So many people have covered Leonard Cohen's now standard that whatever poignancy it once packed has been diluted by countless reality-TV karaoke singers over the past decade. But Jeff Buckley's haunting take from his debut album 'Grace' remains the pinnacle of the song's not-too-long path to fame. His tragic death adds to its resonance.

Bat for Lashes' 2009 album Two Suns is a concept record about a self-destructive young woman named Pearl who plays foil to Lashes' Natasha Khan's more peaceful side. But that doesn't make this somber piano ballad any easier to take, as the character searches for some connection. "Are you my family?" she asks in the very first line. "Can I stay with you awhile?" By the end of the song, however, her black heart surfaces: "It won't be long until you break / Because I'm evil."

There are plenty of moments on Portishead's terrific 1994 debut where despair envelops everything around it, turning even cheerful songs (which, admittedly, there are very few) into crawling dirges. "Roads" is filled with so much hopelessness, in its music and lyrics, that it really doesn't matter if the war Beth Gibbons is singing about is a personal or global one. "I got nobody on my side, and surely that ain't right," she sings, fighting back sadness.

As with the National (see elsewhere on our list of the 25 Sad Songs That Will Make You Cry), we could fill an entire website with songs by indie-rock sad sacks Red House Painters. "Katy Song" comes from their second, self-titled album, and it connects the pieces of a relationship over a dirge-like melody. "I know tomorrow you will be somewhere in London, living with someone / You've got some kind of family there to turn to, and that's more than I could ever give you," Mark Kozelek sings. One of his final lines is one of his most heartbreaking: "Without you, what does my life amount to?"

What is it about rivers that are so damn sad? (Bruce Springsteen's song of the same name is just as depressing.) PJ Harvey's "The River" -- from one of her most downbeat albums, 1998's Is This Desire? -- is all melancholy piano notes and her scarred wail. "Like a pain in the river / Like the way life scattered / To be washed away slow," she sings, hoping redemption will surface from the baptism.

It's no secret that Chan Marshall (who records as Cat Power) has some emotional problems. It gives her music real-life edge and despair. And on this song from 2003's You Are Free, one of her most focused albums, she and pal Eddie Vedder lay down some hushed intensity over jagged guitar and a string arrangement by Beck's dad. But it's the words that cut deepest: "I want to be a good woman, and I want for you to be a good man / This is why I will be leaving, and this is why I can't see you no more."

Tori Amos often demands more from listeners than most are willing to give. As she's gotten older, she's gotten more complicated and frustrating. But those traits stretch as far back as her debut album. "China," however, is one of the most straightforward songs she's ever written and recorded. It's about a relationship falling apart, but with lines like "Sometimes I think you want me to touch you / How can I when you build the great wall around you?" it might as well be the end of the world.

Don't be fooled by the title of the Pernice Brothers' debut album, Overcome by Happiness. It's a sad, mournful affair throughout, filled with depressed, lonely and heartbroken folks who've pretty much given up hope. "Chicken Wire" is the album's most melancholy number, relating a suicide. "They found her car still running in the garage / She'd come so far to end her life," Joe Pernice sings over an equally crushing melody.

How deep is Conor Oberst's loneliness in this song from Bright Eyes' third album? Well, for starters, there's this: "You see your breath in the air as you'll climb up the stairs to that coffin you call your apartment." And this: "You sink in your chair, brush the snow from your hair and drink the cold away." And finally this: "You need something to fill up the days." No hope in sight, in other words.

Several songs from Iron & Wine's second album, Our Endless Numbered Days, could have made our list of 25 Sad Songs That Will Make You Cry. But "Naked As We Came" tugs the hardest at our hearts. Over soft, acoustic guitar, Sam Beam sings about a pair of lovers facing their mortality and making plans for their inevitable futures: "She says, 'If I leave before you, darling, don't you waste me in the ground.'"

This mournful ballad, like many of the songs on Amy Winehouse's breakthrough album, charts the troubled singer's life, circa 2006. This one is about the rocky relationship with her on-again-off-again boyfriend, who had left Winehouse for an ex whose drug-and-boozed-out lifestyle ultimately had a destructive effect on both him and the tragic singer.

We could fill a whole list of 25 Sad Songs That Will Make You Cry with National tracks, but we'll stick with just one: This somber cut from 2004's Cherry Tree EP. Sad-song musical hallmarks like cello, acoustic guitar and a dirge-like rhythm are all over "About Today." But it's the woeful tone of Matt Berninger's vocal that seals the refrain, "How close am I to losing you?"

Like most of the songs on Sufjan Stevens' breakthrough album Illinois, "Casimir Pulaski Day" comes with a history lesson: Pulaski was an American Revolution officer whose holiday is celebrated in Illinois. But Stevens' song is way more personal, detailing the death of a young girl from bone cancer. "On the floor at the great divide / With my shirt tucked in and my shoes untied / I am crying in the bathroom / In the morning when you finally go, and the nurse runs in with her head hung low," he sings as the music tries to find some peace within the pain.

At times, Morrissey can be lyrically obvious to the point of artlessness. Other times, like on "I Know It's Over," he's purposely vague. Whatever the song is about -- a depressed young man, a heartbroken dude, a person coming to terms with his mortality -- it's certainly one of the saddest songs the Smiths ever recorded. Just listen to those chords and the ache in Morrissey's voice.

"No Surprises" was the very first song Radiohead recorded for their historic OK Computer album. And it sets a mournful tone, with gently ringing instruments bubbling over Thom Yorke's near-whispered opening lines: "A heart that's full up like a landfill / A job that slowly kills you / Bruises that won't heal ..." Yikes. With this much despair and hopelessness swirling around, it's a wonder he found time to fret over technology.

Verve frontman Richard Ashcroft has never come clean as to what "The Drugs Don't Work" is about, but it's a pretty safe bet that it has to do with some combination of both his father's death and his own drug abuse. The opening line -- "All this talk of getting old, it's getting me down" -- offers a clue. But it's the refrain of the chorus, "The drugs don't work, they just make you worse," that carries the darkest, heaviest shadow over the gloom.

Norm on Cheers was an affable guy, quick with a joke and probably not a bad person to be sitting next to as you drown out your sorrows. But that's no life to live, as Paul Westerberg relates the sad, lonely existence of the barfly in "Here Comes a Regular." "Everybody wants to be special here / They call your name out loud and clear," he sings over spare acoustic guitar a million miles away from the Replacements' usual slash-and-burn. But the truth is far more depressing: At the end of the song, he heads home alone, and will start it all over again tomorrow.

If you're not listening closely, you may mistake Ben Folds Five's hit for a breakup song or a cut about a relationship slowly turning sour. But make no mistake: "Brick" is a first-person account of a young man torn apart by his girlfriend's abortion. As if that wasn't bad enough, it happens on the day after Christmas. "I walk down to buy her flowers and sell some gifts that I got," he sings, fighting back tears.

You know you're in for a rough emotional ride when a song begins "Your eyes are almost dead / Can't get out of bed / And you can't sleep." Piano, played by fingers that sound like they weigh a ton each, and ghostly cello serve as accompaniment to this downer of downs about a sad life coming to an end. What were you expecting from a song called "Holocaust?"

Weezer frontman Rivers Cuomo received a letter from a fan who claimed to be an 18-year-old Japanese girl. Being the sort of introverted singer-songwriter who would instantly fall in love after receiving a letter like this, Cuomo indeed became obsessed with the girl, but chose to never meet her, in fear of meeting the letter's true author. So he wrote "Across the Sea" instead. It's a sad story, no matter where the truth lies. There's obviously love there, but for Cuomo, the eternal dream beats temporary heartbreak.

After nearly a decade of playing alt rock's resident oddball and smartass, Beck got all serious on his seventh album, Sea Change, which chronicled a particularly tough breakup. Over a spare acoustic backing, Beck channels mid-'70s soft-rock singer-songwriters as he comes to the realization that his seemingly perfect relationship has come to an end. "I'm tired of fighting for a lost cause," he sings, the heartbreak evident in his fragile voice.

Prince wrote 'Nothing Compares 2 U,' but Sinead O'Connor totally owns it, taking the song (and its album) straight to No. 1 in 1990. And who can resist the strikingly minimalist approach to this sad breakup song, in which the Irish singer counts the hours since she got the devastating news. "It's been seven hours and 15 days since you took your love away," she sings in the opening line, tipping us off from the start that obsession has taken a painful turn. By the time she gets around to checking out the garden -- "All the flowers that you planted in the backyard all died when you went away" -- hopelessness has pretty much taken over her sad, sad life.

Robert Smith has a reputation as a doom-and-gloom guy, and for good reason: Eighty-five percent of the songs he's written for the Cure are pretty depressing. But "Pictures of You" has them all beat. Smith supposedly wrote the song after a fire destroyed part of his house. He found among the ruins a wallet containing pictures of his wife. He used that as a launching point for one of his saddest songs, which is either about a devastating breakup or a death. Either way, so, so sad.