40 of the Saddest Songs of All Time (VIDEO)

There are a lot of things a songwriter can do to try to elicit emotion from a listener. This is how we’ve ended up with some of history’s saddest songs. These songs can make you feel the sadness, loneliness or desperation that motivated the song in only a few short minutes. They’re little pieces of heartbreak set to music. Before we jump in, I’d just like to take a moment to mention the lack of country music on this list. Country music takes sad to a whole new level so I decided to do a separate list of the saddest country songs that I hope to post sometime in the near future. I would’ve included them on this list but it’s long enough as it is and even this list is nowhere near complete. So there’s the explanation. Let’s get to the songs that did make it. Listen with an open mind and an open heart, grab a tissue and let’s dive into the darkness.

Adele – Someone Like You

Beneath the powerhouse vocals of one of our generation’s most talented musicians, Someone Like You tells the story of a woman who learns her former flame has moved on while she remains in love with him. It’s a pretty gut wrenching song but the real emotional punch comes from Adele’s truly heartbreaking delivery of the lyrics.

Amy Winehouse – Back to Black

This song isn’t on this list because Amy Winehouse died. This song is on this list because of its no holds barred, brutally honest lyrics. While there are a ton of breakup songs out there, few of them really tell a story in such an open way. I bought the album Back to Black because I couldn’t get Rehab out of my head but this is the song that made me a real fan.

Anna Nalick – Wreck of the Day

Although on the surface this is just another ‘love gone wrong’ song, it’s really about a lot more than that. It’s about making mistakes and suffering the consequences. It’s about how things can pile on a person until they feel they have no choice but to buckle under the weight. The simplicity of the music perfectly frames Anna’s beautiful voice that conveys all of the emotion expressed by the lyrics.

The Beatles – Eleanor Rigby

This is a weird one for me. It wasn’t until I really stopped and listened to the lyrics that I understood how dark this song actually is. Telling the story of poor Eleanor, this song is all about loneliness, isolation and a life lived sadly alone. The music gives the lyrics a sense of urgency. When I really finally got it, I felt a strong desire to immediately call my mother and tell her I loved her. Yeah, it’s that kind of song.

Ben Folds Five – Brick

It’s easy to miss the meaning behind this one if you’re not really listening to the words, so let me help out. Ben Folds wrote the verses of the song about the abortion his girlfriend had when they were in high school. The lyrics are honest and open but don’t take any real position on the subject. Instead, Ben shares what it feels like to go through such a profoundly painful experience without justifying or condemning the act.

Billie Holiday – Gloomy Sunday

This song is absolutely crushing; a straightforward song that doesn’t get bogged down with metaphors and hidden meanings. Billie doesn’t waste any time implying things but just sings them flat out. This song is about a woman who has lost someone she loves and is considering suicide to be with that love again.

Blue October – Hate Me

Sometimes doing the right thing for someone you love means making them get as far away from you as possible. This song is about that exact thing. It’s about making someone hate you and driving them away so they can move on with their life and find happiness because you know you’re only dragging them down.

Bright Eyes – Lime Tree

I don’t know where to start with Lime Tree. The heartbreaking simplicity of this songs arrangement perfectly matches the stark loneliness of the lyrics. Starting off my addressing abortion and the feelings of loss and emotional emptiness that comes along with it, the song travels to some extremely dark places and you’re left wanting to give the poor kid a hug – and maybe curl up in a corner and cry for a while.  I had originally considered writing a list of the saddest Bright Eyes songs but decided to just put this one. He has plenty more though. I would also recommend The Movement of a Hand from the album Fevers and Mirrors or Landlocked Blues, Poison Oak or Lua from I’m Wide Awake It’s Morning if you want to let Bright Eyes break your heart a little more.

Bruce Springsteen – The River

Bruce has said this song was written about his sister and his brother-in-law; two people married too young who are left looking back on their younger days and everything they could’ve had but don’t. The Boss has never been one to hold back when it comes to lyrics and this song is no exception. It’s honest and real which is perhaps what makes it so moving. There are no metaphors; just the story of a man looking back at the dreams he once had and the reality he now lives in.

Carly Simon – That’s the Way I’ve Always Heard It Should Be

Carly Simon is a legend and with songs like this one, it isn’t hard to understand why. Written about the pressure to settle down and get married despite growing up as a child of an unhappy marriage, Carley sings it like she lived it – probably because she did. The lyrics of this song are so truthful. It almost feels like you’re listening to someone read their diary aloud. The words paint a picture and that picture isn’t very pretty.

Coldplay – The Scientist

There are a million sad songs about breakups out there but very few of them tell that story as honestly as Coldplay’s The Scientist. It’s a song about the end and the struggle to accept that it is in fact over. The man in the song wants so badly to go back to the way things had been between he and his estranged lover but nothing can make that happen. I remember hearing this song for the first time. I had just gone through a particularly rough break up and this song damn near made me suicidal.

Damien Rice – The Blower’s Daughter

At first listen, The Blower’s Daughter kind of sounds like a sweet love song. Listen to it again. It’s actually a heart destroying song about love gone wrong. It’s simple but oh so beautiful. When Damien sings the lyrics, you really believe him. You believe he feels every bit of the emotion he’s singing about and that’s probably a big part of why this song is so moving.

Elliott Smith – Miss Misery

This song breaks my heart every time I listen to it. Simple but heartfelt, Elliott Smith pours his heart in this one. It’s honest and it’s rather brave when you really listen to the lyrics. It’s not a love song. It’s a song about loss, sure, but it’s a loss of self Smith is singing out rather than the loss of a lover. Powerful and stripped down, this is a beautiful song well deserving of all the praise it gets.

Elton John – Candle in the Wind (Original recording)

Elton John’s reworking of the song as a tribute to Princess Diana was beautiful and really paid tribute to a woman who had so much life left to live but it doesn’t hold a candle – no pun intended, I swear – to the original. Written in memory of Marilyn Monroe, Candle in the Wind was a perfect and loving tribute to one of the most tragic figures in Hollywood history. Absolutely incredible.

Eric Clapton – Tears in Heaven

Of course everyone knows the story behind Tears in Heaven by now. Written after the tragic death of his young song, this song is about a father’s pain and desire to be reunited with his son while coming to terms with the fact that reunion just can’t happen. You’ll probably be hard pressed to find a list of the saddest songs ever written that doesn’t include this one somewhere.

Evanescence – My Immortal

If I had to guess, I’d say every single pop, rock or country album has one song about breaking up and how much breaking up sucks. It’s hard to make a break up song that really stands out from the pack but Evanescence definitely accomplished that with My Immortal. Haunting, emotional and packing one heck of an emotional punch, My Immortal is the ultimate breakup song.


Feist – Let It Die

As Evanescence did with My Immortal, Feist does with Let It Die. Moody and almost dreamy, Let It Die talks about all of those things you think about after a relationship ends. It’s about the kind of breakup that leaves you questioning the very idea of love and whether or not the whole thing is even worth it. Feist pretty much nails it when she sings “the hardest part of a broken heart isn’t the ending so much as the start. The tragedy starts from the very first spark, losing your mind for the sake of your heart.”

Fiona Apple – Never Is a Promise

Fiona Apple’s lyrics have always been like poetry set to music. They’re deep and layered with meaning which can sometimes make it hard to discern what a song is actually about. I like that. It leaves things open to listener interpretation but that isn’t the case with this one. Never is a Promise is a heart on the sleeve ballad about giving yourself over to someone – letting them in even though your afraid. Does it work out? Does it end badly? It doesn’t matter. This song isn’t about the end, it’s about the beginning.

The Fray – How to Save a Life

I’m not entirely sure what How to Save a Life is about. Is it literal? No one seems to know for sure. There are theories, of course. Some think it’s about a suicidal friend. Some think it’s about addiction. Some think it’s about touring. I think it’s about trying to help a friend with an addiction find a way to a healthier life. It’s  the kind of song that really stays with you regardless of what you think it’s about.

Gary Jules – Mad World (Tears for Fears cover)

The original Tears for Fears version was pretty sad but when Gary Jules took this song and put his spin on it, magic happened. The emptiness expressed in the lyrics of the song are reflected beautifully in the sparse, bare bones arrangement of the music. This was a beautifully executed cover and it remains one of the most hauntingly heartbreaking songs I’ve ever heard.

Harry Chapin – Cat’s in the Cradle

There are lots of songs out there about the relationship between father and son, but this one is a horse of a different color. In Cat’s in the Cradle, Harry Chapin sings about not having much time for his son when his son was just a little boy. As his son grows, their relationship changes. His son grows from the adoring little boy to a busy man who no longer has time for his old man. The line, “as I hung up the phone it occurred to me, he’d grown up just like me” gets to me every time.


Janis Ian – At Seventeen

A song for those of us that never really fit in – those of us that always felt like we were on the outside looking in. The thing about being an outsider is that it’s often hard to remember that, at one point or another, everyone feels that way. For some of us though, at one point or another is an all the time sort of deal. Janis Ian recognized that and wrote an honest, open song about how that feels to not be one of the pretty girls that all the boys like.

Jeff Buckley – Hallelujah (Leonard Cohen cover)

Leonard Cohen has stated publicly that he thinks this song needs a rest and I agree. It seems there are a million covers but Buckley’s heart wrenching take is definitely one of the finest interpretations out there. Sure it gets overused but it isn’t hard to see why. It is one of the most beautifully performed versions of an incredibly beautiful song. I miss Jeff Buckley. So does the music world. There has never been another like him.


Luther Vandross – Dance with my Father

I’ve heard this song covered by about a million different artists but no one has ever quite captured the honest, heartbreaking emotion of the original song. If this one doesn’t make you cry, it’s entirely possible you don’t have a heart. The ending of this song brings tears to my eyes every time I hear it. The honesty and emotion is absolutely moving and anyone who has every lost someone close to them should be able to relate. I’m getting a little teary eyes just thinking about this one.


Madonna – Oh Father

Sia did a version of this song that’s brilliant and wonderful, but nothing can top the Madonna original. It’s a song from a woman to her abuser. You can take it at that or you can read into it further. Perhaps it’s written from the perspective of a woman who has killed her abuser. Perhaps it’s a woman singing to her abusive father. The actual, literal meaning isn’t nearly as important as the emotion the song stirs up. This is, without question, my favorite Madonna songs.

Martina Sorbara – All in Good Time

It kills me – absolutely breaks my heart – that Martina Sorbara isn’t one of the biggest names in music. Her album The Cure for Bad Deeds is flawless from start to finish but this song is the shining star. Another break up song, this one is special in that it captures the desire to move on even when you don’t know how to do that. I’ve listened to this one on repeat through some truly awful breakups because it provides the perfect soundtrack for a really good cry. It also shows strength and poise however, especially with the line, “I’ll face you smiling whether dying or surviving.” Beautiful.

Nine Inch Nails – Hurt

I wanted to keep this list as small as possible (believe it or not, it’s the truth) so I wanted to limit my selections to one song per artist. Hurt had to win out for Nine Inch Nails because of its brutal honesty but it was definitely a tough choice. Something I Can Never Have is slightly less soul shattering than Hurt so it was cut but boy, this one was tough. Do yourself a favor and check out Something I Can Never Have if you’ve never heard it though. Heartbreaking.

No Doubt – Don’t Speak

I know some people might disagree with this one, but honestly, I think Don’t Speak is one of the most amazing breakup songs to come out of the 90s. The lyrics capture all that angst and depression so beautifully and while I’ve never been a huge fan of Gwen Stefani’s voice, you can really hear the emotion behind the song shining through in her voice. It’s not just about losing a lover, but losing a friend. Brilliantly done – one of my favorites.

Pearl Jam – Black

Eddie Vedder refuses to talk about what this song is about. It could be a breakup. It could be a death. It doesn’t matter what the song is actually about. That’s for the listener to decide. What matters here is the way the song makes the listener feel. There is so much emotion in the way Eddie sings this song. The music is relentless. This is a song about pain – regardless of what has caused that pain. Perfect.

Queen – Too Much Love Will Kill You

In the first draft of this article, I was picking out the saddest lyrics and putting them in a little caption at the end of each song description. This song is the one that changed my mind about doing that because from beginning to end, this is one sad song after another. Freddie Mercury’s story is definitely a sad one and makes this soul-crushingly sad song even more poignant.

Radiohead – Creep

This song was pretty much my anthem as a moody, depressed teenager. It’s a song about feeling isolated. It’s a song about not feeling good enough or feeling like you just don’t fit in. This song is pure angst poured into a words over crunching guitars. Thom Yorke alternates between mumbled confessions and pained, dramatic wails; bringing tears to the eyes and goosebumps to the skin. Radiohead’s No Excuses is also a complete soul crusher.

Sam Cooke – A Change is Gonna Come

Sure it’s been covered about a million times by about a million different people but there’s nothing like the original. Full of pain, strife but an overwhelming sense of hope that things will change, this song is absolutely brilliant. There’s a reason people say music these days just isn’t as good as it used to be. It’s hard to imagine a contemporary song that stacks up to this one.

Sarah McLachlan – Angel

Forget the fact that this song is now forever associated with sad looking animals in need of a good home. Sarah McLachlan’s Angel was a heartbreaker long before that. A song about isolation, depression and giving into the sadness and sorry, this song has some of the most incredibly beautiful lyrics ever written. She captures the feelings of loss perfectly and sets them to music.

Sheryl Crow – Always On Your Side

I had a very, very hard time with this one because it was nearly impossible to choose between this one and her response to the war in Iraq, God Bless This Mess. Check out that one as well because it’s incredibly moving. I cut it off this list, but expect to see it on the country list that’s coming soon. As for Always On Your Side, it’s absolutely heartbreaking. It’s hard to really offer anything new when it comes to break up songs but this one is a killer.


Stone Sour – ZZYXZ Rd.

Holy mother of crow, this song absolutely kills me. The first time I heard it, I nearly wept and I mean that in the most literal way. I’m not exactly sure what the lyrics are about. Some say they’re about vocalist Corey Taylor’s desire to leave the music industry. To me, they seem to be about suicide. Perhaps it’s a combination of the two or none of the above. Regardless, the song is absolutely brilliant. I would like to state for the record that I absolutely hate Slipknot and am not a big fan of most of Stone Sour’s work but this is still one of my all-time favorite songs.

Terry Jacks – Seasons in the Sun

Seasons in the Sun is the sad song to end all sad songs. A letter written for the death bed, if you aren’t moved by this one, there’s a good chance you don’t feel human emotion. You might want to look into that further. Singing to a friend, his father and his daughter, this song captures the fear of knowing you’re going to die but also the acceptance that it’s a fact you can’t avoid.

Tori Amos – Spark

Tori Amos is a strong, confident and driven woman. She’s also a brutally honest woman, addressing subjects in her songs many performers wouldn’t go anywhere near. Such is the case with Spark. Written following her tragic miscarriage, Spark addresses the heartbreak and pain of such a horrible event with Tori’s trademark, unflinching honesty when she delivers the line, “she’s convinced she could hold back a glacier, but she couldn’t keep baby alive. Doubting that there’s a woman in here somewhere” near the beginning of the song. To hear a woman whom, to many of her fans, seems super human confessing such a deep vulnerability is startling but incredibly moving.

Travis – More Than Us

Travis’ More than Us is the kind of song that sweeps you up in it’s general epicness and then breaks your heart at the height of all the drama. The lyrics are, as always, beautifully written and the music perfectly compliments the mood set by those words. This isn’t just a song about a breakup. It’s a song about uncertainty and pain. It’s a song about not knowing if you can handle the pressure. It’s a song we can all relate to at one point or another. Masterfully done.

Weeping Tile – Dogs and Thunder

So I hope you’ve all made it this far into the list because honestly, if I were putting this list in order by sadness, I would put this at number one. As I was choosing songs to include, I played this one for my husband because he’d never heard it. I stopped it about halfway through because I started crying and felt like a dumbass. It’s that kind of song folks. Written about making the painful decision to say goodbye to a beloved pet, it perfectly and beautifully captures the emotion in a moment filled with sadness and sorrow. PETA probably hates this one.


White Lion – When the Children Cry

I don’t think I could name another song by White Lion if I tried all day but my husband suggested this one and after listening to it once, I knew it had to be on this list. An honest and emotional song for the new generation, apologizing for the mess we’ve made of the world and hoping they can do what it takes to make it better. It’s powerful and heartbreaking because it’s one hundred percent true.