Top 10 Saddest Songs of All Time

Music has the incredible power to evoke emotions and transport us to different places and times. One of the most powerful emotions that music can elicit is sadness. Whether it's heartbreak, loss, or despair, some songs have the ability to move us to tears and remind us of the raw emotions that we often try to hide. This top ten list aims to showcase the saddest songs of all time, songs that have the power to break our hearts and make us feel vulnerable and emotional.

The list includes songs from a range of genres and time periods, from classic ballads to modern pop hits. These songs have resonated with listeners for years, and their emotional impact continues to touch new generations. So, grab a tissue and get ready to take a journey through some of the most heart-wrenching and melancholic songs ever created. Here are the top ten saddest songs of all time.
The Top Ten
1 Tears in Heaven - Eric Clapton

Many guitarists these days, with a few years of experience, can pick up a guitar and play famous riffs by so many great guitarists and perfect them, but no one will ever be able to replicate how Clapton plays because they lack one simple thing - emotion. I don't mean emotion in general. His "Unplugged" album was so perfect precisely because it was so real. He had the courage to share what he was going through with the world. The loss of one's child is the most painful thing a person could ever go through, and he persevered. He turned his pain into something so beautiful, which will stay with me forever. The acoustics on this album are just sheer perfection. This is so much more than a "sad" song. It's the deepest and most personal song on this list. He wrote it. He performed it. He went through it. We know his story, and it means something to us - something we can't even begin to describe with our vocabulary, and he captured the essence of it so perfectly with this song. His live ...more

His son, Conor, died at the age of 4 or so. Clapton, after divorcing his wife and mother of his son, started to see his son very rarely, as he stated he "didn't understand what being a dad meant."

He decided to see his son more often to build a strong relationship with him since he loved him deeply. But the thing is that he didn't get enough time for that: his son fell through the 49th window of his mom's apartment and died.

Eric has to live with the burden of his dead son. He falls to his knees in grief.

In my opinion, this song is the defining work of Eric Clapton's career. Sure, "Layla" is a fun song to listen to, but it's something of a light pop song and gets boring after the first half. "Tears in Heaven" captures the emotions of a devastating personal tragedy: the loss of not just a friend, but of a son. Few songwriters could channel their emotions into music so beautifully.

Eric Clapton wrote about his son. It's real. There is nothing more devastating than losing your child. Relationships mean nothing compared to looking at yourself in a tiny form and having to watch it die.

2 Hurt - Johnny Cash

At the bottom of everything, extreme emotion is surprisingly void. Instead, a numb calmness takes over. The only way to know if emotion even exists is to hurt, metaphorically or literally. Johnny sees all the fake people living fake lives, lies called society. He produces artificial happiness to fit in with society, taking drugs to feel happy. At least he used to use heroin. His old vices and cruelty give him long flashbacks. He cannot erase what has happened in the past. He once had problems with these drugs. He wants to give everything he can to his wife, making up for his ruined heart. His fame is not important because of these bad decisions. He wants to warn them. He will hurt them! He thinks he is entirely worthless. If he could have a second chance, he would do it all over again, being pure and whole as a man.

Even though I prefer the original version a little more, I will admit that this cover is absolutely one of the best covers I've ever heard. To the point where I cry even more than the original. From the dying, frail voice of Johnny Cash, the clean and happy-but-sad chords of the guitar (mixed in with the perfect atmosphere of the piano), to the change in the original's meaning and the tear-jerking (and I don't mean this in a bad way) music video, it is undoubtedly hard not to love this cover almost as much as the original, and in some ways even more.

Although it's normal, Johnny Cash's voice is cracking when he sings it, almost as if he's ready to cry. It adds substance to the song, as he sings about his regrets and how he's turned into something that he has come to hate, something that has hurt him and everyone around him. This can connect to anyone with a mental illness, or who has done things that can't be forgiven. It can connect to anyone, big and small, because the lyrics hold power and meaning.

1. I would like to say that some of the songs on this list are total bull. I mean, where are you now? That is one of the most lifeless and generic songs I have ever heard. Songs like Snuff by Slipknot, Jeff Buckley's Hallelujah, or So Far Away by A7X are power ballads where you can feel the emotion that the artists put into the songs, making them capable of transporting you to another place entirely. This is one of those songs. The lyrics and video tell the story of a legend who was a shell of his former self before his death seven months after its recording. Songs like these are the true emotional powerhouses, not the garbage that makes up some of this list.

3 Yesterday - The Beatles

This song brings me to tears because of certain memories that, while sad, make my life seem just a little better and brighter.

Four years ago, my great-grandfather passed away due to a terminal illness. Before he was sent to the hospital, he got up in the middle of the night and played this song on the guitar while singing it to my great-grandmother, who he woke up. She sleeps in a rocking chair for whatever reason.

I remember waking up in the middle of the night to hear the sound of the guitar for one minute, then recording the whole scene on my phone while sobbing and choking on my tears the next. They saw me and told me to come in, and we proceeded to finish the song and then sing Blackbird and Let It Be.

When I went home (my family lives in another part of the country), I learned how to play the songs that we sang that night, and now I'm pretty good at those songs. I can proudly say that I'm really skilled with a guitar.

Last year, my great-grandmother ...more

If there's anything that can break your heart, it's nostalgia. Like in the third verse of Firewood by Regina Spektor. Nostalgia is a very powerful subject and a nice change from the usual love songs. There are too many of those.

How can this not be at number one?!

Paul McCartney wrote this about his mother who passed away. It's so heart-wrenching just listening to this song. It makes you reminisce about better times.

Let it be written in stone that the Beatles are one of the rock bands that shaped the minds and hearts of today with their lyrics and tunes. "Yesterday" could ring in my ears forever.

4 Wake Me Up When September Ends - Green Day

Green Day is my all-time favorite rock band. I remember the first time I heard this song was in the morning before going to school. I was probably in first grade, and my mom changed the channel on the TV to MTV Hits. That's when I heard this song for the first time. I really liked this song even though I was small and didn't really understand the meaning of it. After that, I would always turn on MTV and hope that they would show the video. Today, I love this song even more because I understand the true meaning of it, and it's so touching. Whenever I listen to this song in September, I think about 9/11. One of the best rock songs out there. Love it! Amazing!

The time of blissful happiness has gone away as autumn enters, and now you have to deal with the harsh realities of life and death.

As the end of summer comes closer, you naturally get older as you are about to go back to school again.

Green Day lead singer Billie Joe Armstrong wrote this about his father, who died of cancer on September 1, 1982. At his father's funeral, Billie cried, ran home and locked himself in his room. When his mother got home and knocked on the door to Billie's room, Billie simply said, "Wake me up when September ends." People only become what they really are when they feel pain, so that they can't hide their real personality anymore. You get to know the real character of somebody only in extreme situations where limits are exposed.. The feeling of loss will never disappear.

Schools use bells to signify the end or start of classes, and is thus a sound that children hate to hear, especially after a carefree summer. It's just one more step of ...more

This song used to make me cry. The first time I heard it, I was 4 years old and I was told that it was a song about a kid that enlisted in the U.S. Marine Corps and he wishes to sleep through basic training. That is all I can remember from it. That was one of the greatest days of my life, and it has been almost ten years. To me, this is one of the greatest songs ever written. I am very happy to see this on the top ten list.

Although it might not be the saddest song of all time, it touched my heart and made me cry. I felt strongly compelled to vote for it. It doesn't hurt that I love Green Day, either. The meaning behind the song made me even sadder. Billie Joe wrote it about his father, who passed away in September when he was ten.

5 My Immortal - Evanescence

She hurts badly for multiple reasons, I think, both emotionally and physically. She and this guy were very close, and losing him was like losing a part of her. Time can't erase the wounds of her loss, and unbeknownst to her, she's reopening the wounds by holding on to him. When she was upset and crying, the person she lost would wipe away the tears and make her feel better, and also protect her from her fears. Although they stayed with her in spirit after passing and continued to protect her, she cannot seem to let go of them and their memory.

The course of this song makes me sad because it's basically saying that she has been with this one person for a long time and now she just lost him and can't get him back. Which makes me feel really sad because, well, whenever someone passes away you can never see them again, and if you had something really important to say to them, you can't anymore. Whether it's because you wanted to say sorry for something you accidentally did, or if you wanted to tell them something extremely special, or what if it was a family member or your own child. You wouldn't be able to apologize for whatever you did by accident. You couldn't say that special thing that you wanted to tell them. You probably might not have been able to say goodbye to that family member of yours, and if it was your own child, you would be heartbroken because they are supposed to live longer than you are, and they probably weren't able to try new things or even completely grow up. Now I know this because of too many TV shows ...more

Soon after I heard this song, my most beloved cat died. So now, this song happens to be the one I sang during the little funeral I had for her. It makes me burst into tears every time I listen to it.

No doubt, the song struck me to my heart and a brief story. I loved being at the Indiana Jones Epic Stunt Spectacular at Disney's Hollywood Studios in Orlando, Florida, as an extra with host Mindy. For years, we were the very best of friends, and by March 2020, we were on the verge of something special in our lives when the coronavirus hit Disney, shut everything down, and broke up our friendship. When I think of Mindy and that show, I break down into nonstop, uncontrollable tears. Let's hope this show reopens so that we can finish some unfinished business.
Its Joeysworld.

6 Stan - Eminem

A song with a story.

Basically, a fan of the artist Eminem, named Stan, writes letters to Eminem. He can really relate to Eminem in the first verse. As the song goes on, he begins to get more distraught, naming his daughter after one of Eminem's songs (Bonnie), talking about his Uncle Ronnie, who he hasn't sung about at all, and other things. On verse 2, he gets a bit crazier, saying that he thought it was messed up that Eminem didn't answer fans, though Eminem gets tons of fan mail every week. Stan gets angry when Eminem does not give his little brother, also a fan of Eminem, an autograph; they stood in the cold to get it. At the end of verse 2, Stan makes the threat that he will no longer be a fan of Eminem if he doesn't get a response. This is clearly an empty threat, as he has shown deep levels of obsession so far. However, it does demonstrate that Stan is ready to take action if he doesn't get a call, which foreshadows the ending. As it turns out Em does lose ...more

I hate this song because every time I hear it, it brings me to tears. In my opinion, it's the greatest song he ever wrote. The raw emotion put into every single word, the way he visualizes the fall of Stan from an ordinary fan into a horrible person, makes this a pure masterpiece. I don't care about your opinion of Eminem and his controversial ways. You cannot deny he is a genius.

As much as I am not a big fan of Eminem or rap in general, this was a really great song. Unlike the songs above, which can lead to sadness, this song has sadness and anger emanating from Eminem. You can really hear the depth of emotion in his rapping, and the video shows it a lot.

Well, this song is sad - hell, yes, it is - but the way Eminem describes the feeling of a fan makes it seem like he is singing for me, or for us. Don't we all feel like this for our favorite band or artist? You want to live with them, smoke up with them. The lyrics are so intense. Nobody has written something like this in the last 28 years. He may be the god of rap, but his songwriting is above all. No one could have even thought to write a masterpiece like this. Though I listen to metal, Eminem may be a rap god, but he is metal as hell. This song captures all the emotion and makes you want to rap like hell. It's a masterpiece of emotions.

7 Wish You Were Here - Pink Floyd

Wish You Were Here is addressed to Syd Barrett, an original member of Pink Floyd whose mental dysfunction led to his departure from the band. He was replaced by David Gilmour. Barrett wrote most of Floyd's debut album, The Piper at the Gates of Dawn. "Shine on You Crazy Diamond" is also a tribute to him, and The Wall is viewed by some as his biography.

Definitely the best. This song is about the iconic ex-guitarist for Pink Floyd, Syd Barrett. It is about how, though Syd was alive at the time, it was as if he was dead. His brain was dead from all the psychedelic drugs he took, and he was clinically insane. He lived out the rest of his life in his mother's basement, by law. So sad.

I've never understood how this song is sad. Yeah, the lyrics are pretty deep, but the tune to me doesn't sound sad at all. This song is so overrated. High Hopes, which wasn't even on this list until I added it, has moved me more.

How I wish,
How I wish you were here.
We're just two lost souls swimming in a fishbowl,
Year after year.
Running over the same old ground,
What have we found?
The same old fears,
Wish you were here.

8 How to Save a Life - The Fray

This song is absolutely incredible. The lyrics are very meaningful. The singer, Isaac Slade, has a very unique voice that's unlike any other. We can feel his emotions throughout the time he sings this song. This song is definitely the saddest song of all time, and it is absolute genius. How to Save a Life is my favorite song ever.

This song makes me want to cry. It's nostalgic now, but I remember all the times I've been hurt, even physically, and remember the times I really wanted to die. I felt worthless. This song makes me feel sad, but I remember it all. I do regret wanting to die. Although I feel foolish, as I sit now, I want to fall asleep forever.

One time, I actually saved a life when I was deployed. This was the only song I had on my iPod, and it got me through the bad times. Like this if you also love the troops.

This song is very sad because it discusses death, whether from disease or suicide. I can relate because I have lost someone very close to me, one of my parents actually. This definitely triggers tears, even if you haven't lost someone.

9 Stairway to Heaven - Led Zeppelin

This song makes me sad but also very excited. I just love it! It's easily one of the best rock songs. And the lyrics feel so passionate! If you watch the live version, Robert (the lead singer) says, "You know, I feel like this song's about hope." Then the famous guitar riff hums its way in and the crowd is bawling and screaming their lungs out. And the live version is amazing as well. But this song overall is just so beautiful that it's sad. I think that's why I vote for it. It's about the natures of life and how precious life itself is! Stairway to Heaven, in my opinion, is easily one of Led Zeppelin's best works and one of the best songs of all time.

I don't know why this is even on this list. How on earth can you take this for a sad song? And if you listen very hard, the tune will come to you at last: To be a Rock, and Not to Roll? Stairway is, quite possibly, the most powerful rock and roll song of all time. It's all there, the whole package. I remember it being voted the #1 song by radio station listeners in San Diego (on KGB's yearly poll back in the day) several years in a row. With good reason. Definitely not sad or depressing whatsoever!

If you really pay attention to the mood and beginning lyrics, it is very sad and should be number 2, beside Bohemian Rhapsody, which is about someone innocent being executed and these are their final thoughts.

Wow! This song has adrenaline in the solo! Robert Plant's best work! No need to mention Jimmy Page's guitar solo, which symbolizes rock guitar! Great song with great lyrics and guitar!

10 Hello - Evanescence

I'm not even going to lie. Last week was easily the worst week of my entire life as of the day I'm writing this comment. This may sound like an exaggeration, but I lost one of the most amazing people I ever knew, and admittedly, I've had it pretty good. For 15 years, this is the first time I've had to go through a major family death, and it's probably also one of the hardest I'll ever have to go through as well. This song was already sad before, but now it actually hits home for me like no other song has before. That's not all, though, because on top of the child in the song losing someone close to them, it starts with them in denial until they have to see it for themselves. This beats "My Immortal" by a mile, in my opinion.

I think that this song is much more depressing than "My Immortal" because it's about a young child, at first in denial about a loved one's death, who then sees the body for themselves, and my tears start forming.

This song is a song that only a few people know, but it is amazingly beautiful. I would say that it's my favorite Evanescence song. You will just love this song if you don't know it.

I was having a bad day and I ended up bawling my eyes out pathetically when I first heard this song. I actually learned it on the piano. I still listen to it and play it all the time.

The Newcomers

? Would've, Could've, Should've - Taylor Swift
? Heather - Grandson
The Contenders
11 American Pie - Don McLean

I listened to this with my grandfather (it was one of his favorites) when I was little, all the time. He died 3 years ago, and I miss him so much. I can't listen to the song anymore because I couldn't stand the pain.

I'm not sure how sad this song is, but it carries a lot of emotional memories for me. In school, we would sing a song at the end of each year, and this is the one we sang the year that my friends all moved away.

That's why I listen to The Saga Begins. But even that is still sad in the end. Weird Al can't make me laugh with this song, no matter how much I love the melody or Star Wars.

Such a nostalgic song, and an incredibly deep one at that. But once you begin to connect all the lyrics, it's so sad. Don McLean is good at making songs like that.

12 Mad World - Michael Andrews

I was waiting for this to show up. It honestly saddens me that it's so low on the list (52). Just listen and tell me it doesn't leave an impact. In a short few minutes, everything about life is reflected, and we realize just how much we've had to go through in this Mad, Mad, World...

Such a sad song. Most will know this from Gears and Dom's death. Gears incorporated this song greatly. It's just such a sad but good song, and at the same time, it gives me a good feeling that's unexplainable.

Every time I hear this song, it makes me want to curl up in a ball. The words are so thought-provoking and really make you think. It is a mad world, definitely. Just take a moment to reflect...

This song is really sad. Look, I know everyone has their own problems to be sad about, but then there are big things happening on Earth. These things make me sad. The world is mad. This song has the best explanation for that... Got to be higher!

13 Last Kiss - Pearl Jam

This song is the saddest thing I've ever heard. It is the ultimate embodiment of regret and love lost. I cannot believe that it is all the way in the top 40.

I used to hate this song but then my boyfriend passed away last year and ever since then I listen to this song all the time...

A really sad song about a boyfriend and a girlfriend getting in a crash and the girl is dying so he has one last kiss before she dies.

Though I'm not a big fan of love songs, I was shocked not to see this one here!

14 Hero of War - Rise Against

This, Wake Me Up When September Ends, and I Miss You. I picked this song because it is the untold story of a soldier and the horrors that you face if you were or currently are a soldier. I think the most emotional part of this song is the first line and then the refrain at the end: "He said, 'Son, have you seen the world? And what would you say if I said that you could? Just carry this gun. You'll even get paid.' I said that sounds pretty good." Just a masterpiece and one of RA's best songs. Wake Me Up When September Ends deserves its top-five spot because it has a double meaning. It is a tribute to the loved ones of the victims of 9/11, but it is also a tribute to Billie's dad who died when he was seven. "Like my father's come to pass, seven years have gone so fast. Wake me up when September ends." Both are really great and emotional songs.

This song brought tears to my eyes with its beautiful lyrics and message.

This song is much different from Rise Against's usual stuff, and it is by far Rise Against's best. The guitar, Tim's voice, and the lyrics are what make this song so powerful.

This song is sad because it is true. War is depicted as cool and awesome when really, it is everything but that. This shows a soldier learning this the hard way. No one sees the dark side of war. "Is that all they see? Just medals and scars. So damn proud of me."

This is personally my saddest song.

The first time I heard that song, I found it pretty boring because of the lack of speed and guitar and drums in it. Then the second time, I listened to the lyrics and at the end, I burst out crying into my pillow because I didn't want my parents to see me. It's the first time I've cried in years! The lyrics are so powerful!

Once I saw this title and began to play it, it made me cry. Truly, it's so hard to be a soldier and a keeper of peace. Right now, they are here in our country helping out our devastated people hit by Typhoon Haiyan. Salute to these heroes, and thank you for the quick response. The eagle is always watching.

15 Dance with the Devil - Immortal Technique

The only reason this isn't higher is because nobody knows about Technique. In this song, he's not a rapper but a storyteller. This song just moved me to tears, and I hadn't cried in years. Dance with the Devil is about how far you're going to go to look cool for the public. It's ridiculously sad and inspirational at the same time.

How is this not at least in the top 10? If this isn't the saddest song ever written, I don't know what is. The first time I heard this song, a friend showed it to me, and by the end, I was speechless. When people hear this song, it gets to them. It tears at your heart, and you feel for the guy. No song even comes close to this one.

During the last verse, when that line comes (I don't want to spoil it), you'd better hear it yourself. You will be stunned! It's not at the top because people don't know about this song and Immortal Technique. Another sad song by him is You Never Know.

I guarantee that everyone who has heard this song voted for it. I love Eric Clapton and Tears in Heaven is beautiful, but this should be number one. The only reason it isn't is because not enough people have heard it.

16 Creep - Radiohead

I love this song. Everyone at one point has probably felt like a loser, someone who doesn't fit in. Creep is also beautiful in the sense that it captures how you feel like everyone around you has perfect lives and are literal angels compared to your rotten, stinking self.

There are plenty of Radiohead songs sadder than this one. Fake Plastic Trees, Street Spirit, Let Down, and No Surprises are much more depressing.

Expresses the feelings that everyone gets at some point in their lives. If you haven't heard it yet, listen to it and you'll understand.

Definitely. One of the most depressing songs I've ever heard, too. And come on, everyone has heard it at some point. It's a great song to write (or drink) to.

17 Hurt - Christina Aguilera

Every time I hear this song, I cry my eyes out. I've lost both of my parents, but this reminds me of my mom. We didn't have a perfect relationship, and I always felt that I wasn't good enough. As I get older, I realize that she was trying her best. I didn't always understand her. The lines in the song:
Would you tell me I was wrong?
Would you help me understand?
Are you looking down upon me?
Are you proud of who I am?
leave me in a puddle that takes me hours to recover from.
Christina's vocal emotion is spot on! I love this song with every fiber of my heart.

It's 2013, and I still cry during this song, remembering my father. I cry, cry, and cry, even if I've listened to it around 100,000 times and a half. I cry. And it's Christina who made me cry because she's so amazing, so perfect, and so stunning, even after all these years of living. My father would have loved the song, and I wish there was a way I could show it to him.

My best friend and I performed this at our talent show at school, and everyone loved it. It is amazing and strong inside and out, and now every time I hear this song, I remember all those beautiful memories and I just can't help myself but cry.

A deep song. At first, I thought it was about a love relationship. Later, I learned that this song is telling us to appreciate the ones who are always behind our back, supporting and guiding us. Thank you, Christine, for making Hurt beautifully with your undoubted voice!

18 Fix You - Coldplay

Yes, this song is sad in the beginning, but it soon becomes inspiring at the end. I think that Amsterdam should replace this song. That song is filled with suicidal thoughts and depression. Don't get me wrong though. Fix You makes me cry every time, but it comes when the guitar comes into play, just because that sudden change in mood is so powerful.

Come on already. Tears in Heaven is still a sad song, but not many people can relate to it. Fix You has lots of different verses that can relate to lots of different people. Plus, the organ and piano help to make it sound even more depressing, instead of just Chris's voice. The guitar part helps make it even more emotional and motivating, like you've got up to the thing that's making you sad. This should be in the top 10, and maybe even first, but that's a bit too much to be honest. - mathyfox441

It's so sad - shows the desperation at the start (when you try your best but you don't succeed, when you get what you want but not what you need). This gives way to hope for the future, making this song both heartbreaking and uplifting in classic Coldplay style (lights will guide you home... and I will try to fix you).

You know, I never cry hearing Everybody Hurts or Hurt by Johnny Cash, but there is something about this song that makes me tear up every time. It's beautiful, it provokes tears, and should be much higher on this list. Having the song in my head, I'm crying while writing this. I love Coldplay.

19 The Long and Winding Road - The Beatles

This is probably the saddest song made by The Beatles. It's basically a tribute song to John Lennon after his death. It's very touching and bittersweet.

Why did I have to submit this? It's almost as sad as Yesterday, which is like the North Star of sad songs.

20 So Far Away - Avenged Sevenfold

This song is about the passing of the Reverend Tholomew Plague (Jimmy Owen Sullivan), who passed away in 2009. The band, Avenged Sevenfold, decided they will not go on without Jimmy. But they might possibly have another album coming out (for all you A7X fans out there!). Jeez, I'm such a fangirl! But anyway, that's why I voted for the song. Because it's about an ACTUAL PERSON, and well, I LOVE AVENGED SEVENFOLD!

Keep calm and listen to Avenged Sevenfold, people. They have a song in Black Ops 2 called "Carry On." LOOK IT UP. IT'S AMAZING.

You simply feel it there, that painful loss of The Rev. This song is actually full of life for me because it is about someone who really lived. It has soul. And that's the reason why I vote for So Far Away.

Ok, the fact that it's #48 makes me feel sad. This is a terribly sad song, because the Rev is one of the greatest drummers of all time. The fact that the music video only makes it more sad is something that I'll always remember. RIP Rev. A7X foREVer.

This song was written in memory of the band's drummer, The Rev. We will always remember him as the drummer with a unique voice for the chorus of multiple songs, as well as this song, as it marks his legacy.

21 Everybody Hurts - R.E.M.

"When the day is long, and the night, the night is yours alone. When you're sure you've had enough of this life." It's a beautiful and touching song from one of the best albums of the '90s and, of course, one of the most influential bands in the past 30 years.

This is the saddest song ever. I've listened to most of the songs on this list, and this is the only one which has me steadily crying throughout the whole song. Maybe it's just me, but this is by far the saddest song I've ever heard.

This song is sad but it's also hopeful. At first, it makes me want to sit down and bawl my eyes out, but then when that final part comes in and Michael Stipe starts singing "hold on, hold on," I just get up and think that things will get better in the end and I will get through hard times.

This is definitely one of the saddest songs in history! It makes me cry every time, not to mention it goes head to head with You Raise Me Up.

22 Open Fields of Grace - Jackie Evancho

Actually, I would have picked 'Teaching Angels How to Fly,' but it is not listed. Written by James Breedwell and given to a then 9-year-old Jackie Evancho to sing about a girl named Kimberly who died very young. The parents wanted a song dedicated to their daughter. There are several YouTube clips of it.

From her latest album "Awakening," this piece will bring tears—especially if you've recently lost someone near and dear to you. More so than "To Where You Are." Guaranteed.

No words to describe it...

23 He Stopped Loving Her Today - George Jones

This song tears away even the toughest person's fear of crying in public. Upon hearing the lyrics, I am reminded of every lost love that will never return to me and how terribly sad I am to have been left behind with nothing but pictures and videos that haunt me. To my son who just passed away, I say, Hold the lamp high, Matt. I'll be there soon.

Country music has always had a major role in expressing sorrow, along with Blues. This is the quintessential sad song of the South. Nothing is more Country than this sad song about "love her 'til you die."

This song has to be #1. I am not a country fan, but this song is unbelievable. If you click and listen to this song, it will definitely move up the charts where it belongs.

This song always makes me cry. My grandma always plays it because it hits home for her. Her husband died, and this was her song of sadness.

24 Dear Agony - Breaking Benjamin

In my top 3 favorite songs of all time. It's about the feeling of your life just fading away, and you're fighting until the end and more. Also, I deeply miss a friend who had this as his favorite song, so now I cry every time I hear it.

I remember the song Blow Me Away was my first song by Breaking Benjamin, which I heard on the radio. I looked for more songs by him and listened to them, but when I heard this one, I had no idea that Breaking Benjamin could be that sad.

By far the saddest song by Breaking Benjamin! I still love it, though. If you actually listen to the lyrics, it just makes you feel really down.

The voice of Benjamin Burnley is full of pain. It's like you can feel it, and it gives you an inexplicable desire to cry.

25 Hymn for the Missing - Red

WHAT! 318?! ARE YOU KIDDING ME? Trust me, you haven't heard a real sad song until you've heard this one. Every single time, this song will get you straight in the feels. It's so soothing and beautiful to the point where it leaves you in tears afterward. If you haven't listened to it, you really should!

Great song from a totally underrated band.

Probably should be higher on this list. The instrumental piece at the end is really good.

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