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 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

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

The first time you listen to this song, sure, its sad, but you just cannot cry. The second time you listen to this song, you will notice tears rolling on your cheeks. But it strikes me the most how I remember every single detail of the story while listening to the song on its own. When len appeared to rin, when len killed miku, when len died... EVERYTHING, and I mean you will remember EVERYTHING. Then you will see that you are going to cry (or want to cry) whenever you listen to servant of evil again...

It really is sad because it is about a twin brother sacrificing his life so that his twin sister would live, even if she kinda deserve it.

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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. - ArtyLily

This is the first tragic song I ever heard because I like there other songs like gemini and magnet then I saw this I cried a lot

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!

At the end I didn't realise that I was crying.
And this song reminds me of "the boy in slipped pijamas".

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3 Witchcraft Maiden
4 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

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

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 ...more

Why it isn't the first?! Yes, I cried when I listened to servant of evil but I have to watch it for the second times to have me crying! And I actually cried when listened to this for the first time... It really break my heart when I listened to this song (TT)

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5 The Disappearance of Hatsune Miku

This is very sad... To be with someone and getting attached to them, and getting deleted by them suddenly is so sad. Especially the part where she knows its because of her, but she still struggles to pour all her gratefulness to the person for all the good times they had, all the way to the end... ;A;

I found this really, really depressing because, just imagine if when you were born, you found out that you were just a figment of someones imagination or that you were the last one left and slowly fading away, even if everyone was smiling at you as you disappeared, fading from everyones memories, it's still depressing.

How can anyone forget the "farewell song at highest speed"? And all the depressing lyrics at the end. She tries so hard to tell "Masutaa" how much she want to sing... That she's being deleted right after she was installed... And even though she doesn't sing well, she wants to fulfill her dream so bad...

This song is very sad. She literally sings about how she is going to disappear from the world and everyone is going to forget about her, but she won’t forget the great times she had.

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6 Regret Message

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.

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.

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.

Servent of evil is very sad, but regret message ‘s music is sad, Rin’s crying face make my heart crying. I think regret message should be number one!

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7 Fifth: The Pierrot

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

Wait... But Fifth the Pierrot isn't really said. Are we talking about "Pierrot"? Cause that was sad

This song made me cry, I thought it really did explain how she felt about what people think of her

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

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8 Paradichlorobenzene by Kagamine Len

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.

It's about his extreme frustration with the world with its rules with all the crap he just wishes to be crazy in his own way and it's fine and since it's not he wants to sleep

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

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

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9 Soundless Voice

How is this one not at least in the top ten? Anyone who has ever lost a loved one (so basically EVERYONE) is prime game for the feels with this song.

I just can't hold my tears back if I hear for this song.. Really, I'm Fall in Love with this song.T. T

This song made me cry even though I love this song

This one was just amazing! My god, I am crying right now T-T

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10 Proof of Life - Rin Kagamine

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 ♡

This, along with Soundless Voice, is as sad as heck.

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.

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The Contenders

11 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...

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12 Rolling Girl

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

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.

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.

This song is depressing. I cried the first time I listened to it and ever since that first time I listened to it if I was feeling sad.

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13 Kokoro by Kagamine Rin

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

This song is about a Scientist who had lost his daughter/wife/sibling/someone close to him and made a robot (Rin) out of grief. He was almost done with the project before he passed away. Centuries later, the robot seemed to have awoken itself. It's AI was intelligent enough and was able to use her creator's computer and know the password as the scientist gave it to her before dying. The robot tries to find a heart and eventually finds it by searching through the scientist's files/creating one on her own. Finally gaining the heart, she can feel emotions. She sets off to find her creator and comes upon his grave. The robot then sings songs dedicated to her creator before the heart becomes to big for her and short circuits, causing the robot to die/power off next to the scientist's grave. In her last moments, the robot had a smile akin to an angel.

(I'm not sure if this is really true. I just gathered the information from the PVs and Project Mirai.)

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...

This song made me cry so many times. Oh and by the way has anyone noticed that like half the songs on this list are sung my the Kagamines?

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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 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.

The sound is very pretty and tragic

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15 Ayano's Theory of Happiness

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

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


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

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


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 ...more

Ok,so at first I thought this was I peaceful and happy song.Then after reading the lyrics and story I'm starting to realize the true meaning.I was shocked because of how much devotion and love Ayano spend for the 3 and in the end she didn't regret anything and that she act for other's hapiness

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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.

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.

Story about rape, abuse and cannibalism. Pretty strong theme, but great metaphoric message. Kikou is truly a open minded thinker.

Servant of evil is not that depressing. I'm sorry I'm sorry is a haunting song that frightens me.

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

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. - samputen

To be honest, whenever I pay attention to the lyrics of this song I cry. Hear a new cover? I cry. Sing it? I cry. ;_; It gets me every time. It's probably the only song that makes me cry so much too!

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.

This song makes me want to cry! The lyrics, music and PV is even sad! I prefer Mirror's Magic though :P - SeeU

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18 Psychotic Love Song / Yandelenka

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.

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

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.

I cried plus I relate because I love somebody who doesn't love me back

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19 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.

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.

This isn't that depressing

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20 Kept Waiting for a Response

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)

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.

This one is also very sad. Especially at the end.

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List Stats

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Top Remixes (7)

1. Proof of Life - Rin Kagamine
2. Paper Plane by Kagamine Rin
3. Prisoner
1. Proof of Life - Rin Kagamine
2. Kokoro by Kagamine Rin
3. I'm Sorry I'm Sorry - Hatsune Miku
1. The Servant of Evil by Kagamine Len
2. Prisoner
3. Witchcraft Maiden

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