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  • "Kokoro". The song is sad enough, but combining it with the video pushes it way past the "jerker" phase.
  • Eraser Girl by Maretu. Think ’All The Things She Said’ if it was j-metal. Yeah, exactly like that.
  • Re_Birthday is part of the Clockwork Lullaby series, not the Daughter of Evil series, so it might not even be connected. Even if it is connected, the series implies that everyone was horrible in their past lives and are being punished by becoming Vocaloids.
    • It's generally considered that Re_birthday is part of the Clockwork Lullaby series, while being a response to Regret Message, connection which mothy has confirmed in supporting materials. And it's more of a redemption. Len's forgiven from for his sins and given a chance for a new life (with the very people he'd killed/been killed/etc, even).
    • Len's Append just took Re_Birthday to a whole new level of sad. Here, have a listen. Grab a tissue.
  • The Kagamine twins seem to be the masters of this, with songs like the aforementioned "Kokoro", the follow-up, "Kokoro/Kiseki", and things like "Servant of Evil", "Recycle Bin" and the sequel, "Salvage". Special mention goes to "Proof of Life" and "Soundless Voice".
    • "Regret Message" (and "Daughter of White" makes it worse) But "Re_birthday" is there to make everything better!...assuming you actually interpret it to mean he DOES get better
    • "Servant of Evil" is bad enough, but then check out this one fandub video for "Regret Message." Listening to Rin sobbing helplessly as she begs God to give her and her brother one more chance to be happy together in another life, now that she's finally realized what a horrible monster she's been, just... Gah.
    • "Prisoner" and "Paper Plane" are another two that break hearts as if they were fragile china. The highest-rated comment on "Paper Plane" is currently "3:20 total break down." Those of you who've seen the video just KNOW what that moment is. For those of you who haven't, it's when Len starts singing. Sob.
  • VOiCE. No matter how many tissues you have, it will never be enough.
  • Rin's "Flames of Yellow Phosphorous" is not happy. Of course, it's by Mothy. Mothy also wrote moonlit bear, Miniature Garden Girl, The Daughter of Evil Series, and Desert Bluebird. All of which are tear jerkers.
  • Love is War. It's basically Despair Event Horizon: The Song.
  • Reflect by Miku, about a boy who believes he's too unworthy of anyone's attention.
  • Adding to the Rin and Len list, there's Proof of Life and the follow-up Soundless Voice.
  • Cactus and Mirage. The title sounds amusing, up until the main plotline kicks in.
  • Meiko's The Thought To Tell is one of her few examples of this. She's been reborn as a girl, but still retains the love for a girl who was her art student and has been reborn as her best friend. Her friend also remembers fragments of their past life. Do they get together? Nope, girl gets hitched to a guy that looked like who Meiko was in her past life, and poor Meiko attends the wedding to wish them well.
  • * Hello, Planet is extremely depressing, despite the upbeat tone.
    • Its writer has also penned Campanella, a slow, sweet song based off the equally Tear Jerker novel Milky Way Railroad (or Night on the Galactic Railroad, depending on your translation) during which Gumi invokes this trope, first with her attempts to express her feelings to her friend Campanella, even blasting off into space to search for him...but she knows he's dead. What makes it worse is that throughout the video, you see some flashbacks of her life with Campanella. Near the end, when the wham line finally hits, you see an image of a young Gumi watching a crowd of people holding a small box; meaning that she was actually there AT HIS FUNERAL. Tears increased tenfold.
    • And that same creator, Sasakure P, has recently come out with The Week End is Coming! set in the same universe as * Hello, Planet, shortly before the world ends, that has the same theme of trying to reach someone with your feelings too late. What is with this P and writing soul-crushingly depressing songs?...
    • *Sayonara, World's End is a much more melancholy telling of the same story in *Hello, Planet. Goodbye... goodbye...
    • Another song with similar post-apocalyptic robots and lonely rockets motifs is the (sadly untranslated) Summer Rocket. The PV alone still brought this troper to tears.
  • Can't I Even Dream? by Hatsune Miku.
  • You think Servant of Evil is sad? Try the Classical version. And after you're done crying, listen to the Nico Nico Chorus Classical version. * sniff*
  • Dolls by Kagamine Rin. Rin is a doll who is left behind after her master is killed. She sings alone and hopes to go to where he has gone. She eventually falls apart and finds him in Heaven, claiming "I can smile now."
  • Red Swamp Bottom. Miku is singing about being tortured in hell. To understand why anyone would nearly cry over it, see the rest of the Dark Woods Forest series and try not be at least sad over it.
    • Hell, Dark Woods Circus is mostly horror, but it's pretty tear-jerking by itself. For some people. Especially 2:30 onward. "It's fun!"
      • Especially if you know the context: To quote one Youtuber's comment,"I can only tell you that things like this has happend, and still does. Children are kidnapped, and deformed into freaks. For example, they could crush their bones so they grew together wrong, slice things of and more, and the children were also used for sexual services. And if they said no, or tried to escape, they got acid pour in their faces. That's what the flowers in the vid stands for." Now try watching that ending montage without crying. *sniff*
      • It's made even worse after you see the prequel, Wide Knowledge of the Late, Madness. Basically, it reveals that all the circus players were from an insane asylum. Len and Rin's heads were both sewn onto Rin's body, Kaito had the brain of a dog and was eating human flesh, and Miku watched it all happen with a childish curiosity. Just... *shudder*.
  • Are you a dog lover? Listen to Laika, which tells the story of the first animal in space.
  • Depression of the Young Literati. The title tells it all, doesn't it? It's contagious.
  • The Hedgehog's Love is about leaving someone to keep from hurting them, and convincing oneself that this really is for the best and will make them happy.
  • In Ogre and Maid, a blind woman gets lost in a forest and is saved by a terrifying ogre. Not realising that he's an ogre, she becomes his very first friend and makes him believe that humans aren't really that bad. But when he tries to visit her, the villagers run him off and threaten to kill him if he ever comes back. He gives up and goes back to being alone forever, and she patiently waits for him to return until the day she dies.
  • LOLA's English 'cover' of Double Lariat is an ode to The Unfavourite's desperate attempts to get someone to love her, set to perky guitar riffs. It's not the most polished Vocaloid song you'll ever hear, but that just makes it even sadder.
  • Why Don't You Call Me Yet? is about the singer wanting the person she is in love with to call her, while being too afraid that he has forgotten who she is to call him herself. In the end of one of the PVs, Rin kneels on the floor, looking as if she has given up hope as the song ends. After a moment of silence, her phone goes off, to her disbelief. She answers it with a cheerful greeting, only for a final shot of her crying tears of joy to show up, leaving the viewer to assume that the man she loves has indeed called her.
  • For everyone who thought that "Disappearance of Hatsune Miku" was bad, try Teto's version. There are a few lyrical changes, but they make all the difference.
  • Dark Woods Circus
  • Hello How Are You is a song about insecurity. Warning: This one has a high probability of hitting close to home.
  • Secret Crush by Rin is about a girl that loves a boy and cannot ever tell him how she feels because he may be involved with another woman.
  • Mukashi Mukashi No Kyou No Boku, or "Once Upon A Me" is more of a happy tears kind of song, but it might hit too close to home.
  • 69 by Rin and Len. Rin is some form of doll that has lived for 69 years and is beginning to break down and die. Len realizes she is going to be gone soon and tells her that she's still beautiful even though she's falling apart and they both express their love for one another as the song goes on. Rin has an I Want My Beloved to Be Happy moment as she dies, thanking him for caring about her and telling him that even though she's gone, she wants him to continue to be happy and love again. The end of the PV implies that Len is about to suffer the same fate, so she won't be without him for too long.
  • Alluring Secret~White Vow, Miku's response song to Alluring Secret~Black Vow, is utterly heartbreaking. "I can take this black dress off someday..." *Sniff*
  • This song, eight hundred, by Hatsune Miku talks about 6.5 billion dreams coming true and World Peace... Until you fully listen to the song...
  • The Beast. by Hatsune Miku. It tells the story of a girl who trades away her mortality for a beautiful, ageless body. Just... Oh, just listen. Make sure you have tissues handy.
  • Imitator by Len The whole thing is somewhat depressing but the fact that he won't give up hope clinches it as a Tear Jerker.
  • Alice by FULLKAWA P. Hatsune Miku. And then there's the English version and acoustic cover version...Tearjerker, ENE's version. The previously mentioned English dub.
  • Caoin, by Luka. The word 'caoin' is Old Irish for 'lament', so you should know what to expect.
  • +REVERSE and -ERROR by Lily. In +REVERSE, Lily realizes she's fading away, and says, "Even in the flow of time, it seems I can't go against it...When I first realized it by being loved..." In -ERROR, Lily is still dying, and she realizes this, too. She says goodbye to her friends and master...and eventually gets mad because it feels like her master doesn't care. It ends with her saying, "But I still want to breath...Just like the end of the dream I showed you, even works are stuck, ERROR."
  • Gallows Bell. This one cover is especially nice.
  • "Kokoro" now has a drama reading of the manga. Special credits to Mio, who did the professor's, computer's and robot's voice.
  • "Disappearance of Hatsune Miku", which is a happy, cheery song in a major key...about Miku suffering while being uninstalled. Or getting a virus. Or being unable to sing well anymore. Or losing all her memory
  • Eraser sounds so happy, until you find the lyrics. "I want to delete for the all / Since I can't smile / I want to delete for the world / I suppose I'll just walk while crying."
  • "The Heap Princess and Apostrophe", made by the same person that created Hello, Planet. Since it's another post-apocalyptic song, you can see where this is going.
  • From Y to Y. It's melancholy tune and pace just gives a hint of what kind of Break Up Song it is. Then try listening to this well made English dub version.
  • Meltdown by Rin, despite its energetic and happy-ish beat, has a rather depressing meaning. It's vaguely about her future self feeling remorse for her past actions, and she strangles her young self (her past). She can't take it anymore as the timer ticks down to her "meltdown" when she jumps into a nuclear reactor. Well, at least there's the more positive interpretation of Rin forgiving herself...
  • "Rolling Girl". There are a myriad of interpretations for it, but most of them are depressing.
  • "A Certain Prostitute's Love" is depressing overall, but the ending still hits hard.
  • Hatsune Miku's rendition of "Cirno's Perfect Math Class" greatly contrasts with the original.
  • Gumi's "Mermaid" shows off the heart breaking nature of the original fairytale all with a happy tune.
  • Miku and Mikuo's "Hikari/Light". Basically think a cross between Kokoro and The Disappearance of Hatsune Miku. Yeah, it's just like that.
  • I want to meet you by Gumi is also one.
  • Miku's Fifteen Years Pursuing A Cute Boy starts out as a nice song about a more than slightly obsessed girl sending a boy poems, and becoming something of a literary genius because of her practice. Cue the Wham! Line.
    • Ditto for VY 2's cover by the same artist, now with a PV.
  • This version of Pierrot never fails to make this troper cry. The kind clown who did all he could to try and make the girl he cared for happy presumably dies, though there is a happier interpretation: His saying that the "lying Pierrot has now vanished" may only refer to the side of him that lied all the time and wore the mask. The last picture in the PV suggests that he may still be alive and happy with his friend.
    • This troper is hit harder by this PV of Pierrot, which actually remains true to the song's lyrics, unlike the above (although beautifully animated) PV. There's something about the comforting words of a child making the pierrot shed his facade that hits me every time.
  • The Dark Reprise of Koisuru VOC@LOID (VOC@LOID in love); Kataomoi VOC@LOID (VOC@LOID in one-sided love)...
  • This troper is very shattered by Little Mermaid sung by not only Miku, but with Meiko, Kaito and Luka. Well, it is based on the original Little Mermaid and not the Disney version, but since when did the prince (Kaito) sacrifice himself for the mermaid's (Miku)voice? That's very saddening depending on how you look at it.
  • Little Traveler can do this to you, especially if you love The Little Prince (like this troper does).
  • There's this song, Somewhere, people are dying. The refrain has lines along of "Somewhere, people are dying / And it's of no concern to me / But I'm still sad". oh, and the person also apologizes to God for being born, not being dead, merely living and being happy.
  • Elsetetra -The Silver Witch-, sung by Luka as the lonely titular witch.
  • In the otherwise scare-filled song, Kaito Ga Uninstall, we have a tear jerker when Kaito is about to kill Rin and Len. If you pause at just the right moment, you can see Len shielding Rin with his own body to protect her. Awwww...
  • Sorry to You - It's absolutely adorable with Gumi's charm, but there's a sniffle-inducing ending.
  • "Let's Kiss, Hiding In A Car", a beautifully melancholy song by Kaito. Might also double as a Crowning Moment of Heartwarming.
  • The fan-created PV for Kagerou Days. It more clearly illustrates what is happening in the song, and really hammers home just how tragic the whole situation is.
  • Last Stage is a hopeful song about never giving up, but its alternate ending, Last Battle is a very depressing song about going on by yourself and running away.
  • Hikari no Kakera, much like Rainbow Girl, Disappearance, and My Honey in the Tragic Dimension, is another song about the master-Vocaloid relationship, and gets the same results.
  • First, listen to Just Be Friends. Then, watch the PV. Then, read the lyrics. The extremely depressing lyrics never fails to make this troper tear up.
  • This relatively new and cute song by the new and cute vocaloid, IA: Imagination Forest.
  • Karakuri Pierrot by Miku. It's about Miku being stood up by the guy she loves, and how even though to him she is just a clown, she's content for him to continue manipulating her.
  • It's surprising that Time Forgotten One by Kaito hasn't been listed yet. It's about a statue doomed to spend his entire life waiting for his long-dead nakama.
  • The Heap Princess and Apostrophe "What do you call it when there's not a soul to love you? No one will love me; I'm all alone." This is one heart-wrenching song because it's about a girl left behind from a war between machines and humans. She thought she was the only person alive until she met a kind robot. "Don't look at me you'll make me cry so many tears", the reason why she says this is because the gentle robot reminds her of someone she used to love [possibly her brother] who died. The robot gets into a fight with other robots and it's implied in the end that both the girl and the robot died as you can see a shot of the crown the robot gave her. "No one has ever doomed with no one to love them. And for you...I was the one who loved you."
  • Cinderella ~another story~ is pretty touching as well. It puts a tragic twist to the classic fairytale in that Cinderella (Rin) has been transformed into a white cat for not returning from the ball at midnight, rendering her forever separated with the prince (Len). This is sung as they both remember the instant they had together, fully aware of this fact.
  • Kept Waiting for a Response, the finale to Story of Evil. And a touchingly beautiful finale it is.

 If my wish really does come true

If my sins have really been forgiven

I want the response to my letter

And will keep waiting for it

  • How have we not mentioned oFFENCe yet? The whole song is about Miku's regret and guilt after she killed her lover in a fit of jealous rage- describing how she still feels his presence and how she can never forget the moment she murdered him. And to top it off, the final verse implies she kills herself too.

 In the first Spring... I met you with an innocent smile on your face,

In the first Summer... You held me tightly in your arms,

In the first Autumn... We swore to "stay together forever"

In the first Winter... Even though... We promised....

But in the third Summer... You stopped laughing,

And in the third Autumn... You no longer held me in your arms,

In the third "belonged to someone else",

So in the fourth Spring... I... I killed you...

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