Most Depressing Vocaloid Songs

So... we all know that Len died like fifty times... which one of them is the saddest? And not only when he dies. Everyone can cry at the Disappearance of Hatsune Miku. So which song made you cry the most?
The Top Ten
1 The Servant of Evil by Kagamine Len

This song is such a tragic story. After being separated for many years Len and Rin are finally reunited, and Len makes it his duty to play the part of making her happy, and having a life she deserves. He could've easily refused her orders to do cruel things, such as kill Miku, but his love for her was everything to him, and he didn't care what he had to do as long as he saw her happy. When many people are going against Rin, Len stood by her side, even though he could've overthrown her evil rule over the kingdom, but he didn't because he cared about her more than himself. When they finally went to kill Rin, Len without question switched places with her, without a care for himself, and he could've easily left her to die, he didn't have to die for her, he chose to do so. He didn't ask her to switch places, he ordered her to, and sacrificed himself so she could have a second chance at life, and when the time came to have him killed, he didn't dare look at the crowd, he knew his sister was ...more

This song was my favorite though I changed my way of view about this song. At first, I was frantically fallen in love with the song that I played it every day or not every time I can spare. I love the way he loves. It's so deep. He's empathetic to her twin sister. HE understand too well that he want to take all of your pain if he can and if not, at least, he can reduce or share with the suffering. He would even sacrifice other important people in his life and even his life that it's so touching. He's very kind... But recently, my way of viewing it changed. Instead of showering it with positive thoughts, I began to realize the negatives. I ignored it at first cause I thought it was unnecessary a small detail which was wrong... Rin became the new queen and great expectations, traps, hatred and jealousy, responsibilities became a must to be met. Rin tried to be strong and her natural soft and kind side became hidden until Len came back to her and ease and help her in every way... In ...more

Servant of Evil. At first I had no idea what Len was saying,I just fell in love with the melody. I later download the song. That's when I looked up the English lyrics. I read the lyrics while listening to the song. The song has so much emotion. I held back my tears and tried to make it through the song without crying. Epic fail. I cried a lot more than I thought. I was completely and utterly confused. Not because the song, but because I felt a weird feeling for this song. I felt the passion, the guilt, the gratitude, the love. I felt it all. Len sacrificed himself to save his twin sister. If that's not love, I don't know what is. Len always dies in songs. But just about every time. It's to show his love. This is one of my favorite songs ever. >w< bai!

This song takes the cake. I only had to listen to this song once to start bawling like a newborn baby. It had a large plot that held feelings and different sides of the same story. It shows that despite the fact that his sister was considered evil and cruel, he still loved her above all and was so affectionate over his twin that he was willing to take her place be killed. The song also shows that the so-called "Daughter of Evil" was not so cruel when it came to her brother. This song was practically a universe of sadness. Overall, no song

2 Prisoner

I saw this a few years ago, and to be honest, the visuals and the brutal story scared me. But when you look into it deeply, it is a very sad story. A boy is taken into a concentration camp and is treated in a horrible way, but then falls in love with a girl beyond the fence and sends paper planes to communicate with her. He knows that he cannot gain freedom, but believes that he can overcome anything if she is there. The girl becomes the light of his life. However, the girl one day says goodbye to him, saying that she is going to go somewhere far away. He then says that living his life full of suffering, he has cried the most in his life that time. He doesn't even know the girl's name, but wants to see her. The girl's father is a general, and finds the letters that the boy and his daughter has been exchanging. He rips the letters and sends the boy into a gas chamber where he dies.. Truly tragic. I also love the guitar throughout the song. Len's vocals are also soothing.

Hello, this is the person who gave an explanation for Servant of Evil above! So... I'm only explaining Kagamine songs now... Anyway, explanation for Prisoner...

There was a prisoner living in a concentration camp, supposedly similar to the Holocaust... One day, he fell in love with this girl across the fence. They traded paper planes for a long time. Until one day, the girl said she had to leave and the boy cried so much... A guard came over later and ripped the planes up in front of the boy's eyes. Soon after, he was sent to the gas chamber to rot. His last wish was to know the girl's name...

This is same as before... Only explanation for events in Prisoner...

Creator: Shuujin-P

Cast:

Len Kagamine as Prisoner 408
Rin Kagamine as The Girl From Across the Fence (If someone knows the real name, please tell me!

Thank You!

Let's get this straightened out: I despise Len Kagamine. I hate him. In the Servant of Evil, I was laughing hysterically. Call me a sadistic jerk, but it's the truth.
Yet something in this song, in the story, just brought me to tears. The prisoner (Len) and the girl outside of the fence (Rin) loved each other so much... And they were ripped apart by one another's own tragic stories.
Rin had a disease and she couldn't walk anymore, therefore she couldn't see Len again. She then died from it.
Len was taken to a gas chamber after he was discovered reading the paper plane messages Rin had given him. In the gas chamber he suffocated.
In Paper Plane, it is revealed that he is reunited with Rin through death, but does that ease the sadness in any way? Not really. Two young, innocent people had their lives taken away.
What really struck a nerve was that it reminded me so much of The Boy in the Striped Pajamas. Memories of that, added to the overall depression that the story in ...more

How is this second! Servant of evil is not sad at all. It has a sad story but still! This is so sad! I love these kinds of forbidden love stories, but UGH, It's just so heartbreaking. At the end, all he wanted to know was her name. They were both slowly dying and all they wanted to do was be with each other. I just don't even know anymore. by the way 10/10 for whoever wrote this song!

3 Witchcraft Maiden
4 Regret Message

Imagine if you were selfish all your life and then your sibling/loved one/someone who would love you unconditionally died for you. You then realized how selfish you where but they were gone. You have to live all alone now, and every single day you send a message wishing that they would only come back, and in all your regret, you fall down to the ocean wishing for them to come back while you scream and cry in the ocean. You then think you see them, but you really don't. You promise to see each other in your next life.. Then you die tragically. Why.. Regret Message made me cry, a lot.

I know Servant of Evil is sad, but Regret Message is even sadder. The PV made me cry my face off (not literally, but you know what I mean... )! In the PV near the end you see Rillane (Rin in Story of Evil) crying her head off, yelling, and screaming while standing (and eventually kneeling) in the ocean. When I saw this part, I started crying with her. Pretty intense. I can't BELIEVE that Regret Message is number 24. I thought it would be Number 2 (Servant of Evil is obviously going to be first. It's Len's most famous death... And more). BUT NO, It is number 24.

Imagine thinking about how your twin just died because of you. Many other people died too. All because of you. Now, you are trying to send a wish into the ocean via a bottle. A message (of regret) in a bottle. You wish you had realized your sins before everything had happened. That is Regret Message for you.

Regret message is the first Vocaloid song to make me come close to tears. Yeah, I know a lot of people think Servant of Evil is really sad (and it's my number one favorite song), but Regret message is like elaborating on the pain you feel when you listen to Servant of Evil. It shows how sorry that Rin is and makes you wish Len didn't die even more than the many other times he died. It shows how cracked Rin's heart was and makes you feel her sorrow. It makes you wonder what would've became of them if they both survived the revolution.

It made me cry, and trust me, that is saying A LOT. Because other than this, I've never, ever, EVER cried over any book or movie or Vocaloid song before, EVER. But this is just so incredibly beautiful. I was crying at the end, when the random scentist guy was saying,
"And now let's indroduce you to someone."
And then Len was standing there.
In the book, that never happened. Rin grew up without Len and became a nun and when she died, she was surrounded by everyone who loved her.
A little different to how Len ended. Oh jeez, I think I'm gonna start crying again.

5 Paper Plane by Kagamine Rin

The first time I ever heard this song, I could feel my heart being torn in two. A forbidden love between an army general's sickly daughter, and a young prisoner boy from on the other side of the large fence that separates the two. When they began throwing the letters to each other in the forms of paper planes; I could tell that both would cherish them greatly, and read through them every chance they got, which they did as shown by Rin. After her father forbids her from any further contacting Len, her illness takes a turn for the worst, but she still goes to see him one final time at the fence. Throwing over the paper planes; she goes to leave when he shouts out to her that he will wait for her to come back, that he will treasure the letters she sent over. This part broke my heart because she knows full well that this would most likely be the last time she ever met him again, and goes to say something, but cannot bring herself to, so begins to cry. The bridge starts and it has Rin in ...more

This, along with the song that comes before it (Prisoner) are probably the most depressing, but beautiful out of all of the songs by Rin and Len. It depicts Len being a prisoner in a concentration camp (most likely Auschwitz from a scene in Prisoner) and Rin being the daughter of a nazi, with sadly no chance to live through her illness. Through communicating using only paper planes thrown over the barbed wire, the two develop a beautiful relationship, and love each other dearly. In the very end, when Rin takes her last breath, in the camp, Len is doing the same. Both taken unfairly, Rin by illness, and Len by force, they meet again above, being able to hold hands for the first time, and both are finally able to be truly free. The story is beautiful, and probably one of my favorites.

This song, along with Kokoro, made me cry rivers. The story is so heartbreaking on so many levels. Rin plays a girl who is rumored by fans to have ALS and is the daughter of a Nazi. She one day meets a prisoner boy (played by Len) who is in a concentration camp and they fall in love. Rin sent paper planes to the boy as a way of communication. The girl kept on coming until a few months later, when she got very sick due to her disease. Also within that period, the prison guards (including Rin's dad) found Len reading the paper planes from Rin. They then went up to him and tore the paper planes to shreds right in front of him. Infuriated, Len punches the guards. Due to this, Len is sent to the gassing chamber, where he is later gassed and dies. Back at the hospital where Rin is being taken care of, the disease has really taken a huge toll on her. She can no longer move and she goes into depression, and she says "If I hadn't pretended to be tough, it would've been fine". The heart monitor ...more

Yes, this song really deserves to be the first in the list. It was so sad it made me cry :'( Some people I know think the way they communicate is just stupid, but I think it was sweet and cute the way they used paper planes. God, while watching this, I REALLY felt like punching the hell outta Rin's stupid dad.

Sure, he cares for her and everything, but he had no right to separate her from Len! I mean, she's sick and probably doesn't have a chance of surviving (I'm really sorry for saying this) so she needs to be happy while she can! Poor Len, he dies in the end too.

Not the BEST Vocaloid song, but I still love it. This song has one of the saddest lyrics EVER. I lost it when they met each other again after dying. You should also check out the music box version; it's very calming and almost as good as the original version, meaning it can also make you cry.

While listening to it (music box ver. ), I imagined Rin and Len sitting under a tree. It was snowing at that ...more

6 The Disappearance of Hatsune Miku

Just Miku signing off at the end with a "goodbye" and "I'm sorry" make me want to hug her a billion and a half time. I don't know, the realization of surrounding and the doubt of it. The realization that "ignorance is bliss but those days are over" makes it extremely sad.

It is pretty sad, but not that sad to be no. 8. It's probably all the Mikutards that voted this. It's just that Miku is getting uninstalled, no big deal. How can you even cry. I hardly feel sad. All my friends (Mikutards) said that this is sad... But how is this sad?! If you really want something that is sad and makes you cry, listen to Servant of Evil, before listening to Regret Message, Daughter of White and then Kept waiting for a response. That made me recreate the Pacific Ocean. If not, listen to Prisoner and Paper Plane or Soundless Voice and Proof of Life. Kokoro and Witch and really underrated, but is much more sadder than Disappearance of Hatsune Miku. The only thing impressive about this song that it is the same speed as Eminem's Rap God

This is a really sad song. My interpretation of it is that Miku's 'master' is disappointed in her, and decides to uninstall her. Realizing this, Miku pleads for her master to keep her, but gets no answer. Desperately, she tries to sing one more song before her time runs out, which is why the song is so fast. She then thinks she is just an imitation of a human being, and that she should accept her fate, trying to remember the taste of her chopped leeks. She thanks her master for everything, and is removed from master's computer.

I never cried, but it's even sadder when I tell you this (I guess). This is what I read somewhere but I changed it up:
This song was created because Miku was being forgotten by the people who liked her, or she wasn't doing so well. So a song was created to let everyone know that this was gonna be Miku's last song. When a lot of people liked it and were listening to it, it encouraged the people who make Vocaloid songs to make more Miku songs. SHE'S BACK.

7 Paradichlorobenzene by Kagamine Len

This is the saddest song I know. I mean, Len feels that he's unwanted and he starts going insane, including breaking all the rules and possibly killing that stray. He just feels sad and he starts going on possibly a rampage. Now he wants this other girl to go insane with him. I even wrote a book (it's very short but very interesting) that's literally the meaning of the song and has some quotes from the English lyrics

Len's frustration with the world shows with the way he tries so hard to defy it. He tries to go against everything in the world, because of envy and jealousy. He sings about how his pent-up frustration is released into the world by means of overwhelming jealousy, knowing that he has no right nor reason to say those things. Rin's counterpart, Antichlorobenzene, shows different views on the same world problems, and also highlights how destructive he became, almost inhumane.

To whoever said "How is this sadder than calalini?! " I think this song is sadder because more people can relate to it. That's why so many people find Hello/How Are You? sad. Many people may relate to Calalini. I think I may KINDA relate. But hasn't everyone experienced that feeling that you just don't get enough attention and nobody cares about you? It's really scary, confusing, and depressing to experience

Not very sad, but it's depressing. Basically about how life means nothing

8 Fifth: The Pierrot

Its about a boy who was a pawn his whole life, working for an organization of assassins. he explains how he loves dancing and performing, but must work for the Pere Noel. When the member Seven asks Fifth to leave with her, he declines and tells Ms.Santa/One. Later, Eight teams up with Seven and they murder Fifth. While it doesn't seem to sad, the joyless of Fifth in the beginning, even him making fun of the word Pierrot make his death much more sad. Even the last sentences are tear dropping. I definitely reccomend this song and the album, the evil chronicles

This song just made me cry, I mean especially with senya's voice and pv. It just like, I can't explain it but you can really sympathize because I'm sure once in out life we tried being a pierrot to someone else. I let my emotionless friend who doesn't cry on sad songs or movies hear and see it and she cried and it totally shock me at how her tears just fell from her eyes like what you mostly see in anime

The first time I heard this song was by Kanseru, and it had the pv with it. I had no idea what it said, but just the video made me want to cry. I listened to other versions and found the lyrics and it is by far the saddest song I have heard.

This song really made me cry, yet it took a few times of listening to it to realize he dies...

9 Re_Birthday

This is an explanation for this song:

Okay first of all you would need to know these three songs:

Daughter of Evil

Servant of Evil (listed in this list)

And Regret Message (short summary: Rin lives on and remembers when Len told her that if you put a message in a glass bottle and put it into the ocean, it will come true one day, so Rin does goes to a beach and does that and wishes that if the two twins were to be reborn, they hope to be twins again.)

Re_Birthday then tells about how Len is in some pitch black place place (in my opinion I think wherever sinful souls go to when they die) where he is chained there to repent for all his sins from Servant of Evil. It then tells about how he got the message from Rin in Regret Message and how he will be reborn in a new time and place (most people think as a Vocaloid).

You thought they turned into Vocaloid? Listen to keep waiting for a response.

I walked around the house aimlessly after watching this.

I found this one more cheerful to be honest...

10 Soundless Voice

I loved the sound of it..just heard it today, I loved the melody of it. I heard in the comments it was sad, but looking at the lyrics got even sadder. How he would want to lose his voice..for Rin.
In fact, I immidiently thought of Hitotsuzuku I figured he made it since he is known to have such depressing songs. Just how isn't this in the top three? This is probably the saddest song I've ever heard, with Proof of Life and Rolling girl coming at second.

Honestly, this song is amazing, despite being sooo sad.. Len and Rin lived together, happily, until Rin died, leaving Len alone and begging to hear her voice again. What makes this sadder is that he keeps on having flashbacks to when she was alive, he knows that she would just want him to be happy, he can't while shes dead. I think the best part of this song is when he goes AHH! letting out his scream of agony. Wheyher Len loved Rin as a sweetheart or his little sister, this song is heartbreaking. (-' o '-)

I feel like soundless voice needs to be recognized. I think we all know what happened in our hearts when Len saw Rin on the snow, dead, and then he lay there with her. The Kagamines stomped all over my heart... Again.

I always support Hitoshizuku and Yama. Especially their stories and operation of vocaloids. The biggest tragedy Blessed Messiah and the Tower of Ai is even not on the list...Porbably because it's a new song?

The Contenders
11 Rolling Girl

Servant of Evil is no more than an overdramatic fairytale. There's nothing to cry about, it's not a true story. There's really nothing that depresses people. Rolling Girl is about a real life issue. Everyday people commit suicide because of their life problems. That's something to cry about. It's about a girl who doesn't feel understood and like she doesn't belong. Like she doesn't deserve to be in the world. People kill themselves for the same reasons. The girl tries to strangle herself and just die to end it all. Yeah a guy who loves her saves her from dying but that's not the point. It has a happy ending to it, unlike Servant of Evil but the story teaches you a lesson. I cried listening to the upbeat tune. The lyrics give it it's true meaning. Listen to Rolling Girl and you shall understand.

This is the most depressing song to me. I've never cried while listening to it (I'm not that type of person) but I can relate to it so much, in so many ways, that I definitely look at life a different way now. I know nearly every person has explained the lyrics, but I'll try to do it anyway. Rolling Girl is about a girl who is (or thinks she is) a failure in life. She's really misunderstood, and it got to the point where she is ready to kill herself so she doesn't have to "roll on." At the same time, though, there is a little part of her that wants to roll on one more time, and that voice, along with all the "stop rolling" and insane voices in her head, overlap and really display what the girl is suffering through. You can get this much from the song alone, but the PV is...well, I don't know. I guess it's sort of relatable? Listen to it if you haven't already. It gets more crowded, the vocals start to sound a little like desperate screams, and the girl is completely ready to commit ...more

Rolling Girl is definitely one of the most depressing Vocaloid songs out there. Let's be honest, here: Servant of Evil is simply a story, one with a sad ending, but hey, it is not at all realistic. Why is it at the top? Because it might as well be one of the most popular Vocaloid songs. But Rolling Girl is so easy to relate to for many people. The girl in the song feels she is worthless. But she keeps telling herself to just keep trying, to keep going, to not give up on life just yet, no matter how painful it is. To be truthful I'm most likely going to end up comitting suicide at some point in my life, but in the span of listening to this song, I felt both miserable for the girl and motivated; motivated to keep rolling.

How is this 9? Sad romance songs do tug at my heart but this one takes the cake. It almost deludes you thinking that Miku at least has someone...until you get to the end and you realize she's truly alone. It's so deep and symbolic that anyone can have their own personal meaning, and I think that's what makes this song truly sad. My interpretation is that the boy, who everyone thinks is 'helping' Miku, is actually her depression telling her to stop living. How heartbreaking is that? When I thought that she at least had this random boy helping her, she really doesn't. It truly represents those who have real life depression and loneliness, and is something that I cry at imagining others actually feeling this much pain and agony.

12 Proof of Life - Rin Kagamine Proof of Life - Rin Kagamine Cover Art

I know most people think Soundless Voice is sadder, but in my opinion Proof of Life is right up there with it. In this song, Len sings his grief as well as in Soundless Voice, but we also get confirmation that Rin can feel him. She IS scared, she IS lonely, she doesn't want to leave and it's hurting her. She's not just the comatose object of Len's song this time, she's a dying girl fighting to thank her brother before she accepts her death and the entire time she's staying strong, "I don't want to sing a sad song." As much as I love Soundless Voice, and as much as I love the twins the same, this will always make Prood of Life just a little sadder for me.

Many people don't know of this song and I don't know why, I've never cried so hard at a song in my life. The main story is about Rin knowing she will die soon and how all she wants is to leave something behind as proof that she was alive. As the song progresses Len begins to sing saying that they share a soul and that he can't take it being alone without her, Rin tells Len to continue to be happy and sing happy songs as that is all she's ever wanted to do and that she'll be by his side so he won't ever be alone. However Rin is scared and feels alone but she continues to be strong throughout the song and at the very end she thanks Len for her life. I've listened to a lot of sad vocaloid songs but this one is definitely at the top of my list and I HIGHLY recommend that any vocaloid fan to listen to it ♡

Since it is the replied song for soundless voice, it made the song so depressing. How rin begged len for singing a happy song and do not want to sing the sad song had depressed me so much. In the soundless voice, by it's melody you know it is a sad song that rin does not want to hear.

This is as sad as Regret Message, Servant of Evil and Soundless Voice. It is so touching.

13 Kokoro by Kagamine Rin

You know when one person is cold as ice and the other wanted company desperately, that's maybe the most depressing situation known by human beings. Len used his whole life to try to make Rin understand "being human" but still she asks him, "Why do you cry? ". Then Len died, with regret because he couldn't finish the kokoro. Then there's my favorite part, Rin gets her kokoro after hundreds of years and Len arrived again. The the part that made me, who never cried once during a video or book, starting to rain tears, was when Rin started crying because of "unknown emotions". I mean, Rin, you can just admit that you miss Len alright...

Well there is two version of Kokoro that I know;The lambada organ version and the normal one. Me and my best friend don't like Rin at the first time so when we found this kokoro video which shows that Rin died me and my best friend are yelling"FINALLY! "but when we knew what's the meaning of this song we kind of cried. Rin wanted to understand humans and becomes one although she's a robot, she thought if she had a heart she could understand them but when she got one it's too much for her to take which made her having some kind of errors and make her programs shutting down. And the Lambada Organ one, Rin was a genius that lived in a free-bacteria lab. She told everyone at first, She's not supposed to be alone, she's supposed to be twins but somehow she was born alone without him. So she tried everything to make a human which will be her twin, and the stupid but sweet part is that unborn human was in a bio-liquid cylinder thingy which will dissolve everything that you put in and it will ...more

When I first heard this song, I was very confused, so for those of you that want an explanation, here it is.
Once, a smart scientist named Len created a robot and named her Rin. When he first creats her, he realizes she is missing something: a heart. (Kokoro means heart in Japanese.) So Len started making this heart. But it takes so long to make a heart that by the time it is finished, he is in his dying days. Once Len dies, Rin goes on his computer and obtains this heart. Once she gets it, she gets to feel all the emotions like happiness, sadness, anger, etc. Then, something bad happens. The heart was too big for her, unable to withstand that weight. So she dies, right next to Len's grave.
Then, Rin and Len meet in the afterlife, where they can be together with each other for all of eternity.

This song is so sad
Although I think it could be sort of linked with the disappearance of hatsune Miku to be honest with you.

And also isn't this song in the start of magical kitty Len Len?

14 Alluring Secret Black Vow by Kagamine Rin and Len

How could this romantic song not be any sadder, Rin an angel makes a deal with the devil to become a boy so Miku would love her and Kaito tries to kill Miku because he was jealous and Rin gives her life for Miku. How in the hell is that not sad.

This is the only song that makes me almost cry. There aren't any Vocaloid song that makes me almost cry even I really did cried at the first time I watch the PV. This complex romance is the best of all!

This has always been one of my favorite VOCALOID songs. It shows how much someone is willing to sacrifice for the person they love. It's a beautiful songs and very tragic.

This has always been one of my favorite Vocaloid songs. Just the instrumental contains so much emotion, it gives me goosebumps. A tragic love that was never meant to be.

15 Ayano's Theory of Happiness

If you watched Mekaku City Actors (Kagerou Project), you would understand the story:

SPOILER ALERT!

One day, Ayano's mom and dad adopted three kids from the orphanage. They had red eyes and weird powers, and were called monsters. Ayano comforted them, saying that red is the colour of heroes, and always played with them.

When the mom dies, and their dad almost dies, the dad is possessed by the worst snake (power) of them all, who will do anything to grant his wish. In order to do this, all the kids with red eyes will be sacrifices.

Ayano, on the other hand, wanted to understand more about this "curse". She went and found her mom's research about it, which says that snakes will possess children that go into near death situations in pairs. One dies, and the other is possessed with the powers. Ayano also finds out about her father.

She decides that no matter how much she wants her mom back, this can't happen. She decides that she wants to save her ...more

Now then, this is definitely one of the saddest songs that I have ever listened to, like, EVER! I suppose if you haven't listened to all the other songs or watched the anime it would be a bit hard to understand why, so basically:

Ayano's father and mother adopts 3 orphans, all of whom has red eyes and strange powers. They were isolated by the other children but Ayano cheered them up by saying that red is the colour only heroes would wear and made up a hero group(brigade or something like that), to make herself have something red as well, she wore a red scarf. But then, their mother died and things just starts to go wrong, with their dad being possessed and thinking of sacrificing the 3 kids who, of course, had done nothing wrong. Therefore, as the good big sister Ayano is, she learns about this curse that the 3 kids have by experiencing near death situations or something and decides to save them, she has to commit suicide, which Ayano eventually did by jumping of a ...more

This is definitely ONE of the saddest. I'd say it's tied with Rolling Girl.
I have bits and pieces from the anime based on Kagerou Project, specifically a few that led me to conclude this:
When you have such a happy life and then adopt (I think) three kids with terrible pasts...and you make them happy again...that's tear-jerking from happiness. Then the mom passes away, the dad seems to fall into depression, and that happy life you had crumbles away in an instant. To save them, you realize you would have to die. Ayano does this in an instant. She cares about the three kids she adopted so much that she dies for them. Now THAT'S sad.
(SPOILERS: If I'm remembering correctly, Ayano's sacrifice was senseless in the end and helped the villain. That doesn't help it much either.)

Ayano loses her mom, she *figuritively* loses her dad, so all she has left is Kido, Kano and Seto. When she finds out about her father's *plan*, she decides that she not only wants to save Kido, Kano and Seto, but also the 2 other kids who her dad was planning on hurting. Ayano's theory of happiness, was for everyone she loves to be safe, and despite the fact that she could've killed her dad and ended it like that, she would rather end it so that possibly, her dad (and not the snake) could remain. In conclusion: *starts sobbing hysterically*

16 I'm Sorry I'm Sorry - Hatsune Miku

This song takes a view on a poor brainwashed girl who is obviously being abused, who decides to run away to be with a man that has been nice to her, only to find out that he is repulsed by her body. In the end, she just gives up and comes back to her abusive father and his friends, all the meanwhile repeating "I'm sorry, I'm sorry, I must surely be a bad girl." This not only shows how abusers can gain the trust of the ones they abuse, but how easily the abused can be broken when they have no one to turn to.

Is it bad that I actually like this song? I don't like it because of the lyrics, video, or idea of the song because those are all horrifying. But, I like the song because I can imagine certain anime characters screaming out this song at a talent showcasing because they couldn't think of anything else to sing. That, and the fact that I like screaming along.

The song isn't exactly depressing in the way you would usually think. It's depressing at how you realize, that, something like this does happen in the world. Terrifying AND depressing. But still a great song.

It may seem really creepy and disgusting but just think about it... I honestly think this is the saddest of all the vocaloid songs I've heard.

17 Magic Mirror (Mahou No Kagami) by Rin and Len Kagamine

When I listened to Magic mirror, I only started crying at the very end when len says "Everything on the other side of the mirror is "the mirror image" of everything on this side. Our completely opposite fates will never permit us to be together. "I merely return to you what you have given me. "

The phrase "I merely return to what you have given me" was just so sad. heres my theory. A mirror is the opposite image of the real thing. since len was the reflection of rin, he was the total opposite of her. So when he grants rin her wishes (curing her illness so she can walk/ ending the war/ allowing her to live a rich life as a princess) he has to return back to his own world where it is the total opposite of rin's world. By granting all of rins wishes, he had to sacrifice his own life. so when he returns to his world, there will be war, he will be poor and stricken with illness while rin lives happily. I feel that this song is so sad because of this ultimate act of sacrifice

I first knew about this song when my best friend told me about it but I was not really clear on the story yet and I still haven't read the lyrics.

Then the next day she explained it again to me and let me hear the song.

I swear as soon as I heard the mirror breaking, I almost choked my best friend. I was really upset after that and my mood went from hyper to depressed at once.

When I first heard it, I cried. I feel the same way Rin does at the beginning of the song, the feeling of being lonely. And as the song progesses, I feel like Rin does in everyway. By the end of the song, I already cried my eyes out. I think why I cry every time I sing it or listening to it is becuase I can relate to how Rin feels.

When I first heard the song, I wasn't even 100% sure what the song even meant because I didn't pay attention to the lyrics. But you can HEAR the emotion coming from Rin and Len. When that mirror broke, I had a mental breakdown, I could not stop crying.

18 Seasonal Feathers

She sacrificed her freedom for someone she loves and it's mutual. It's actually somehow wholesome in context but the chords and notes make it sound way sadder than it looks. "If someday I'm no longer the beautiful girl you love would you still love me?" "yis," I literally cRiED.

Is it weird that I am hearing the song now and crying? I mean I listen to it everyday and I always cry! I was pretty emotional by the end of the song. The feeling of losing someone close to you is a very familier feeling to me and this song help me embrace it all. I love it!

One of the saddest Vocaloid songs I have heard in my life. I bawled my eyes out (not literally) for the next ten replays (which is a record).

Ooh, definitely a tearjerker.

Tissues definitely recommended. You'll probably need at least one box.

19 Psychotic Love Song / Yandelenka

This is so sad, Len was in love with a girl. He was really in love with her. She started hanging out with this other guy. It made Len jealous and angry. His mind fell apart and he murdered her. He immediately regret it after he killed his love. We can only assume from the PV he killed himself after.

Love makes people do crazy things. It has a nice sound to it, but it really is depressing seeing how vocaloid songs are just songs about what happen in life and just get distorted a little. I cried while listening to this because any one of us can do this and that thought is terrifying.

I find this song depressing because it is very real, and also that my favourite Vocaloid sings it. I'm Yandere for Len! Is there anything wrong with that?

Very depressing lyrics and story, but a catchy beat. It can probably fall into the horror category.

20 Witch - Megurine Luka

This song strikes me as beautifully tragic. Miku's jealousy leads her to lie about Luka knowing fully that she will be killed because of it. Gakupo is tricked by her lie and reluctantly believes her. When Luka is about to be burned alive she grows a pair of black wings and flies away. I like to believe the interpretation that Luka was not a witch, but an angel.

Don't think I need to explain more about this. Literally being burnt alive because "tHis wiTch LoVeS yoU iTs pRobAbLy pLotTiNg a murDEr oR soMetHinG!1!". Miku out here ruining relationships hahaa.

This one makes me physically sick with sadness and nerve. From what I've gathered Luka is accused of being a witch so is put on the cross through Miku's Believe and/or jealousy? Anyways, it's messed up. BUT I LIKE IT!

I had no idea what this song was about before I watched it. It made me really sad. I it is also such a good song. I recommend it.

21 The Lost One's Weeping - Kagamine Rin

WARNING: My opinion and interpretation. You don't have to agree.

How the actual heck is this not in the top 10? This is literally the most relatable song out there. Servant of Evil is an overdramatic fairytale that people somehow cry at. Lost One's Weeping covers a real-life issue of how people can break under the pressure and stress of the school system. The boy in the story, like all of us, is forced into education and tries his hardest to do well, and while he succeeds in math and science, he is useless at Japanese. We can see that he begins to have suicidal thoughts as the song progresses, especially in the end.

In the chorus, the boy talks about himself, questioning if they even know how he feels and what he's going through, and if they can stop him from hanging himself. The lyrics become desperate at the end, and the boy questions what growing up is and whether it is worth it. He is uncertain who he should ask. And the last line in this song implies that he hung ...more

Sure, a lot of songs on this list are terribly sad, fanciful stories, but it is songs like 'The Lost One's Weeping' that actually resonate with me. The message behind it is so painstaking, so REAL, that I feel emotional every time I listen to it. It primarily critiques the school system, illustrating how a student's mental health is belittled and interspersed with the dissatisfying and relentless work, and the trapped loneliness of this. If you want to hear a really emotional version, I seriously recommend you listen to MafuMafu, because he really does it justice!

This song explains how a young boy is so pressured to do well in his education that he cannot remember his past dreams and who he used to be, and thinks the only one to blame for this is himself. He contemplates whether or not living like this continuously is the right thing to do, and when the time where he can grow up and escape from it all will come. But he doesn't know what it truly means to grow up or if its even worth it anymore, because if he doesn't find a way to succeed in school his life won't matter anyway.

School...makes me feel like an utter failure.
I remember seeing this in a "most depressing vocaloid songs" video, and searched it up... to see if anyone knew how I felt about school, and that if I wasn't alone.
It became my most favorite vocaloid song, as I could connect with it.

This song was one of those songs in which I could actually see myself...and it will always have a special place in my heart.

22 Kept Waiting for a Response

Although it's not canon as stated by mothy, but it's the saddest song about Story of Evil. It got me every time! I hold the tear to the Kaito's part and can't hold back anymore. There's something in the melody and the lyric make you sad, truly utterly sad

This one, they say took place after Servant of Evil and Regret Message. Rin is now a nun in an orphanage, and she's about to die. You HAVE to see what the orphans do for her. It will make you cry in the end.

I think that this song is the saddest. Not because is the only one that was capable of truly make me sad, it's because the lyrics are depressing. Maybe you will think that they are even if you aren't too sensible.

(Sorry if my spelling or grammar is bad, English isn't my first language)

I always start to tear up at the part where Len and the other kids (Yes, there were other kids! ) found Kaito. Len wrote a fake letter of response to Rin and by that point I was like ". Need more tissue! "

23 Little Mermaid - Megurine Luka

I thought that that everything would be fine but then I heard, I listened, to the very end of the song. I cried. I wonder though, if their were someone, mermaid or not, that still sings for their loved one? Even if they can't hear them, they still do?

This is barely sad. It's beautiful of course. It's amazing and it fits the story really well. It follows the original story more than the Disney version. So don't get me wrong, I love the song. But it never made me sad.

Its just so sad! It follows the original version of the little mermaid and pulls off the mood so well! The lyrics were lovely! And the way it was sung was just wonderfully tragic! I just love it!

I cried so much!

24 Lie by Megurine Luka

I usually listen to vocaloid covers as I prefer to hear emotions. But the tuning of Luka in this song is superb. The sadness is clear in her voice...

I believe most of these songs you just need to experience for yourself to really hear the music right. Maybe some people don't understand, but I do. I feel the struggle all over again in this song, being torn apart by one particular person. That's what makes this song one of my most favorites.

This song is so sad. Especially if you watch the music video. There's so much emotion in Luka's voice and this song will surely make you cry. I personally love this song even though it's so sad and makes me cry every time I listen to it.

This song is probably one of the saddest and most emotional things I've ever listened to. If you're looking for sad writing music, look no further.

25 Just Be Friends by Megurine Luka

Very very bittersweet. Shows perfectly that some things aren't meant to be but sometimes it's for the best. This song broke my heart in every way possible the more I listened to it and understood it. The saddest Luka Megurine song for me.

The music is so good that I listen to it quite often, I don't know Japanese, so when I remember what the lyrics are about, I just get depressed. Every. Time.

This song is just.. I love the beat and tune so much, but every time I hear it al I can think of is a relationship that didn't bring anything but pain.

Such a happy tune... until you read the lyrics and proceed to bawl over your pool of tears

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