Top 10 Most Depressing Vocaloid Songs

So, we all know that Len died like fifty times. Which one of them is the saddest? And it's 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 - 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 watching, and he didn't want to see her cry, he just wanted her to know he was dying so she'd live, it was his choice, and he in no way regrets it. At the end Len states he'll wait until he and Rin can be reborn, just because he loves her enough to spend another lifetime with her, and she meant more than his own life.

2 Prisoner - Kagamine Len

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.

3 Witchcraft Maiden - Hatsune Miku
4 Fifth: The Pierrot - Hatsune Miku

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

5 The Disappearance of Hatsune Miku - Hatsune Miku

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.

6 Re_Birthday - Kagamine Len

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...

7 Soundless Voice - Kagamine Len

Honestly, this song is amazing, despite being so sad. Len and Rin lived together happily until Rin died, leaving Len alone and longing to hear her voice again. What makes this even sadder is that he keeps having flashbacks to when she was alive. He knows that she would want him to be happy, but he can't be while she's gone. I think the best part of this song is when he lets out his scream of agony. Whether Len loved Rin as a sweetheart or as his little sister, this song is heartbreaking.

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.

8 Regret Message - Kagamine Rin

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.

9 Paradichlorobenzene - 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.

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

10 Rolling Girl - Hatsune Miku

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 song had me sad for days. To think that she finally found someone, only to realize that it was just her depression telling her to give up is such a punch to the gut.

The Contenders
11 Kokoro - 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 help the unborn human grow, Rin then opens the cap and jumped in which of course making herself got dissolved into the liquid.

12 Paper Plane - 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 the bed, obviously something wrong with her. Her father rushes in, and comes to her side, only for the nurses to pull him away. Standing outside the door, it shows him in his regular clothes; before changing to have him on the other side of the fence in his uniform. Finding Len sitting in the alleyways reading her letters, and with two guards at his side, he takes the planes from Len and begins reading them and tearing them up. Flying into a fit of rage; Len proceeds to hit him, and begin yelling at him about something that you cannot hear. Judging by the look on the father's face as Len yells this; I'd say that it is something along the lines of how he was so cold that he couldn't even let his daughter be happy, that the two were in love; and that he was a horrible father. Sadness turning into anger, the father lets the guards drag him off as his pride is now wounded, and Len is then thrown in the rooms they use to gas the prisoners; and it fades to black with him enveloped in... more

13 Proof of Life - Kagamine Rin

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 ♡

14 I'm Sorry I'm Sorry - Hatsune Miku

VOCALOID has a way of making sensitive topics like abuse and others into an upbeat song that's catchy and iconic. Like "I'm sorry, I'm sorry". The beat in the song is so catchy and so good, you don't even know that it's a song about a girl being physically and sexually abused until you turn on the subtitles. And that's unique about VOCALOID. They make sensitive topics to upbeat or beautiful songs that kind of teach us something in a way. From scary songs to sad songs. I'm sorry I'm sorry has to be one of the saddest songs ever. And I thought that reboot was sad. Until I heard this. I feel like the moral of this song should be "don't be a pervert, don't abuse or take advantage of anybody, and sometimes not trusting anybody". Because in the song she suffers the consequences throughout the whole so much that her father and the friend that she loved have seduced her at such a young age and that would impact her for the rest of her life. And not to mention it relates with real life struggles as well. Which is depressing and scarring

15 Ayano's Theory of Happiness - IA

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 siblings, so she jumps off a bridge. She is possessed, but when she dies the snake the disappeared, ruining all of her dad's plan.

Them feels though... ;-;

16 Magic Mirror (Mahou No Kagami) - Kagamine Rin and Len

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

17 Alluring Secret Black Vow - 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.

18 Psychotic Love Song / Yandelenka - Kagamine Len

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?

19 Seasonal Feathers - KAITO and MEIKO

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).

20 Kept Waiting for a Response - Hatsune Miku

Len is an orphaned boy who was taken in by an old nun, during his time at the orphanage the old nun, Run, is about to die so he asks her that no matter how stupid it is he will fulfill any request of hers, she says that when she was younger she sent a wish in a bottle and wants a reply to it, Len sets off and finds a painter, Kaito, who explains that she was an evil princess who had done wrong and her twin saved her life by switching places with her, before she dies he writes a reply to the letter and finds her by an ocean, he gives her the reply and Run dies in peace. It is the last song in the Story of Evil series and it sent me to tears.

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.

21 The Lost One's Weeping - Kagamine Rin

This. Song. Is. Amazing. And also really relatable. It's about how the school system puts pressure on people and I don't understand why it isn't higher up.

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 himself because he didn't care anymore, and he decided it wasn't worth it.

"It doesn't matter anymore."

22 Witch Hunt - Multiple Vocaloids

The tune is catchy but the meaning is depressing. It really frustrating and depressing when the person you love doesn't believe you anymore and is one of the people who sentences you to death.

I enjoy it as much as I cried during it. The feeling of betrayal is very unpleasent. Feels like someone stabbed you in the guts or something like that!

I love this song, but never really understood the meaning behind it.

23 Sigh - Kagamine Rin

So Rin was depressed in the beginning, sighing all the time and not knowing what to do with herself. An angel, which was Len, reached his hands out for her to give her a nice time. Rin grasped onto his hands then in her world everything was black with yellow flowers growing around. Angel Len would give her things like teddy bears, flower pots, and many more. One day she was taking care of the flowers when she noticed her world was crumbling down. She saw a vision of some sort that showed Len in a hospital bed, and he had a cloth over his face to show that he was dead. I'm sure that this vision could be when he died before he became an angel, but that's in my opinion. Anyway, so she felt her world breaking and crumbling till it exploded to show only white. This part shows that she opened her eyes finally, and now having to see the real world instead of her own world. She cries out, wanting someone to hold her, and what appeared was Len's angel behind her, hugging her from behind but she hadn't noticed. After all that, Rin decided not to weap anymore over Len's death. She wiped her tears dry, and smiled a forgiving smile, knowing that Len was in a better place now. Then the video and song ended.

24 Anime PV: Reboot - Luka, Miku, and Rin

This was the third Vocaloid song I have heard, but even today I listen to it. Now this is what I call a beautiful song. The tuning, voice, and meaning of it is just beautiful. The song sounds amazing, and it's hard to explain in words. Not only that, but the animation blew me away. The PV is probably the saddest thing I've ever watched. Watching it the second time while I was alone in my bedroom, I just couldn't help but burst into tears. I was sobbing as I heard the voices and watched the PV. It wasn't in a bad way. It was in a way that made me feel good. This song encourages me and makes me feel happy, even when I'm sad. The story and meaning is beautiful, too. I want to thank the person that made this song. It is the saddest Vocaloid song in my opinion. But the fact that Zimi was made for this song and never used again just makes it even sadder...
I can still sing this song to this day as a young Vocaloid fan. This is one of my favorite Vocaloid songs and I still get the feels while listening to it.

25 Wrinkle - GUMI

A song that I will continue to cry to long to the point I have my own fair share of wrinkles.

Wrinkle is definitely one of the sweetest songs I've come across. You gotta love it.

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