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. Len makes it his duty to ensure she has the happiness and life she deserves. He could've easily refused her orders to do cruel things, such as killing Miku, but his love for her was everything to him. He didn't care what he had to do as long as he saw her happy.

When many people were going against Rin, Len stood by her side. Even though he could've overthrown her evil rule over the kingdom, 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. 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.

When the time came for him to be 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. 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 horribly 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, one day, the girl says goodbye to him, stating 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 at 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 have 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

It's about a boy who was a pawn his entire 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 too sad, the joylessness of Fifth in the beginning, even him making fun of the word Pierrot, makes his death much more sad. Even the last sentences are tear-dropping. I definitely recommend this song and the album, The Evil Chronicles.

5 The Disappearance of Hatsune Miku - Hatsune Miku

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 the master's computer.

6 Re_Birthday - Kagamine Len

You thought they turned into a Vocaloid? Listen to Kept Waiting for a Response.

I walked around the house aimlessly after watching this.

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. I just heard it today, and 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 immediately 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 in second.

8 Regret Message - Kagamine Rin

Imagine being selfish all your life, and then a sibling, loved one, or someone who would love you unconditionally dies for you. You then realize how selfish you were, but they're gone. You have to live all alone now. Every single day, you send a message wishing they would only come back.

In all your regret, you fall into the ocean, wishing for them to return while you scream and cry in the water. You think you see them, but you really don't. You promise to see each other in your next life. Then you die tragically. Regret Message made me cry a lot.

9 Paradichlorobenzene - Kagamine Len

Len's frustration with the world is evident in 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. 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 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, on the other hand, is about a real-life issue. Every day, 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. She feels 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 its true meaning. Listen to Rolling Girl and you shall understand.

The Contenders
11 Kokoro - Kagamine Rin

You know when one person is cold as ice and the other desperately wants company? That's perhaps the most depressing situation known to human beings. Len spent his entire life trying to make Rin understand what "being human" means, but still, she asks him, "Why do you cry?" Then Len died, filled with regret because he couldn't complete the Kokoro.

My favorite part is when, after hundreds of years, Rin finally gets her Kokoro and Len returns. The part that made me, someone who never cried once during a video or book, start to shed tears was when Rin began crying because of "unknown emotions." I mean, Rin, you can just admit that you miss Len, alright...

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 the other side of the large fence that separates them emerges. As they began throwing letters to each other in the form of paper planes, it became apparent that both would cherish them greatly and read through them at every opportunity, which is shown by Rin.

After her father forbids her from further contact with Len, her illness takes a turn for the worse. Nevertheless, she still manages 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 they ever meet, and she goes to say something but cannot bring herself to, so begins to cry.

The bridge starts, and it shows Rin in bed, clearly unwell. Her father rushes 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 show him on the other side of the fence in his uniform. Finding Len sitting in the alleyways reading her letters, with two guards at his side, he takes the planes from Len, 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 inaudible. Judging by the look on the father's face as Len yells, I'd say 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. As sadness turns into anger, the father lets the guards drag Len off while his pride is now wounded. Len is then thrown into the rooms they use to gas the prisoners, and it fades to black with him enveloped in darkness.

Months later, the illness has now... 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, saying, "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 "Proof of Life" just a little sadder for me.

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

VOCALOID has a way of making sensitive topics like abuse 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 realize it's about a girl being physically and sexually abused until you turn on the subtitles. That's what's unique about VOCALOID. They transform sensitive topics into upbeat or beautiful songs that kind of teach us something.

From scary songs to sad songs, "I'm sorry, I'm sorry" has to be one of the saddest songs ever. 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". In the song, she suffers so much throughout that her father and the friend she loved have seduced her at such a young age, which will impact her for the rest of her life.

It also relates to real life struggles, which is depressing and scarring.

15 Ayano's Theory of Happiness - IA

If you've 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 color 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 who 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 disappears, ruining all of her dad's plans.

The emotions, 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. 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. Here's 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 Rin's 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. Kaito tries to kill Miku because he was jealous, and Rin gives her life for Miku. How in the world is that not sad?

This is the only song that makes me almost cry. There aren't any Vocaloid songs that make me almost cry, even though I really did cry the first time I watched the PV. This complex romance is the best of all!

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.

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 regretted 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 happens 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.

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?" "Yes," I literally cried.

Is it weird that I am hearing the song now and crying? I mean, I listen to it every day 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 familiar feeling to me, and this song helps me embrace it all. I love it!

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.

21 The Lost One's Weeping - Kagamine Rin

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

How 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. 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 towards 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 whom 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's 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 unpleasant. It 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, and 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, she felt her world breaking and crumbling until 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 weep 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. This is what I call a beautiful song. The tuning, voice, and meaning of it are 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 a 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 are 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, to the point where 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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