Top 10 Most Depressing Vocaloid Songs

So, we all know that Len has died like fifty times. But which one of those deaths is the saddest?

And it's not just when he dies. Everyone cries at The Disappearance of Hatsune Miku too.

So, which song made you cry the most?

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. 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.

   This song just made me cry, especially with Senya's voice and PV. It's hard to explain, but you can really sympathize because I'm sure that at some point in our lives, we've all tried being a pierrot for someone else.

   I let my emotionless friend, who doesn't cry at sad songs or movies, hear and see it, and she cried. It totally shocked me how her tears just fell from her eyes like something you'd mostly see in anime.

4. 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.

   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 going to 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.

5. 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.

6. 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.

7. 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.

   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 feels like an elaboration on the pain you feel when listening to Servant of Evil.

   It shows how sorry Rin is and makes you wish Len hadn't died, even more than in the many other times he has. It shows how broken Rin's heart was and makes you feel her sorrow. It makes you wonder what would've become of them if they'd both survived the revolution.

8. 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.

9. Rolling Girl - Hatsune Miku

   What I love most about Rolling Girl (by wowaka) is that it has a clear theme of a young girl (which I will call Miku) with depression, but it allows for different interpretations. Some also associate the song with bullying, failing in education, and self-harm. On a more meta level, the song can be seen as wowaka expressing his discontent with Miku being credited as the artist of his work instead of himself.

   This song is depressing due to its realistic nature that applies to real issues and the powerful rock sound. Some people take a more literal approach to the boy in the fanmade music video and see him as a romantic partner or friend who supports the girl. Whereas some take a more metaphorical approach and see the boy as a representation of the girl's depression.

   Some people believe Miku closing her eyes, holding her breath, and hugging the boy at the end of the song is her aiming to reduce her suicidal thoughts, as the boy is a support in her life. Others see it as a representation of her leaning into her depression and ultimately committing suicide, most likely in a way related to breathing, such as strangulation or hanging.

   Another interpretation is one more time and I will roll again. Both lyrics can be seen as having positive meanings and also negative meanings.

10. 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...

The Newcomers
11. ?

    Shinitagari - Hatsune Miku

    You want to die is an underrated song. Miku is drianed from constantly being put into the role as a therapist for her friends that use her for expressing nothing but their painful emotions. Miku wants her relationships to be two-sided and tells them 'if you want to die, go ahead and die then', which leads her friends to see that complaint without actions leads to no improvement. Her friends eventually try to see the positives in their lives and start to care for Miku as a friend, not as a therapist.

    So, in this song, Miku is kind of the mom/therapist friend with her own issues too. All of her friends (I'll just say Rin, Luka, and Gumi for now) have their issues that they always complain to her about.

    Rin constantly puts herself in situations where she enjoys the idea of her death. Luka always threatens to harm herself, though she never takes any action. Gumi only speaks of the idea of her suicide.

    Miku, quite obviously, gets annoyed by the constant complaining and unwanted venting from her friends. Eventually, she kind of gives up on dealing with their issues - not telling them directly but thinking that if they want to die, they should just go ahead and die.

    I don't know how to explain it best.

12. ?

    Suicide Song - Hatsune Miku

    

    I think this so is pretty sad and upbeat.

The Contenders

13. 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.... read more

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. 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.

16. Magic Mirror (Mahou No Kagami) - Kagamine Rin and Kagamine 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. Ayano's Theory of Happiness - IA

    If you've 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 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...

18. Alluring Secret -- Black Vow - Kagamine Rin and Kagamine 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.

19. 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.

20. Seasonal Feathers - KAITO & MEIKO

    This is a very emotional song. Len is a human who married a crane (Rin), but he didn't know that she was a crane. The story begins by telling us that the two met on a snowy day like the one in the story. Soon, the setting changes to the season after winter, and Rin is shown singing with the birds. Len says, "You have a nice voice," and Rin asks, "If I no longer have this voice, would you still love me?" He answers, "Of course," with a warm smile.

    Then the story moves into summer. We learn that Len collapsed on the mountain, and since they were a poor couple, they couldn't afford medicine for him. Rin began to pluck her feathers to make a cloth until her fingers became scarred. While she was treating Len, he noticed her injuries but didn't say anything. Instead, he said, "You have beautiful fingers," and Rin asked again, "If I no longer have these fingers, would you still love me?" Len answered, "Of course." Later, he started coughing while holding Rin's hand, and she realized his hand was cold.

    The story tells us that Rin worked through the seasons, day and night, saying she had to finish the cloth faster. She kept saying it was just a little bit more until her fingers could no longer move. Sadly, she was too late. Len's illness took over and killed him. In front of his grave, Rin asks, "If I'm no longer a human, would you still love me?" while placing her last feather in front of his picture. She admits that this was the question she was always afraid to ask him.

    After that, Len's soul appears along with bits of light. He embraces Rin and answers, "Of course. I promise that I'll embrace you when those wings can no longer fly, and also, I will always love you." Rin then breaks into tears, holding his arms around her neck.

21. 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, it's the saddest song about the Story of Evil. It gets me every time. I hold back the tears during Kaito's part and can't hold back anymore.

    There's something in the melody and the lyrics that makes you sad. Truly, utterly sad.

22. 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."

23. Reboot - Megurine Luka, Kagamine Rin, and Hatsune Miku

    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.

24. Witch Hunt - MEIKO, KAITO, Hatsune Miku, Kagamine Rin, Kagamine Len, and Megurine Luka

    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.

25. 15 Years Pursuing a Cute Boy - GUMI

    

    Miku wrote all these poems for a boy that died 15 years ago so she could take them with her to "heaven" when she died. The boy wrote her a letter before he died, saying not to open it until 15 years later.

    Miku gets hit by a train and loses all her memories, except for the one about her love. She doesn't remember his death. She only remembers she loves him.

    So for a few more years, she writes poems for him and throws them into his house.

    Another year, Miku is hit by a train again. She wakes up in a hospital bed, and it all comes back to her, causing her to break down into tears.

    She races out of the hospital and looks for the place the boy buried the letter. She finds it and keeps it.

    Well, what can I say? It made me cry. People say it's stalkerish, but I say it's touching.

26. Can't I Even Dream? - Hatsune Miku

    A song that stays with you for a really long time. A song that someone would sing when they feel like they are left behind, alone.

    The aura of the piece is depressing, yet somewhat pleasing.

    Besides the actual lyrics being depressing, the piano keys you into a feeling of loneliness.

    I don't actually find many Vocaloid songs depressing, but this tops the list.

    About Miku chasing after her prince charming but never reaching him.

27. 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.