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Masterpieces of Vocaloid Ballads [Tear-Jerking / Heart-Wrenching]

When you’re feeling wistful or sad, what kind of music do you listen to?

Some people might choose bright, uplifting tracks.

But I bet quite a few prefer slower songs that seem to stay close to how they’re feeling in the moment.

So in this article, I’ve put together a collection of Vocaloid ballads.

I’ve picked out a wide range, from recent hits to long-loved classics.

I hope you find a song that fits your heart perfectly.

Vocaloid Ballad Masterpieces [Tearjerking & Bittersweet] (91–100)

emptiness/void (kara)Presto

“Sky/Void (Kara)” feat. Hatsune Miku
Empty/Void (kara) Presto

Perhaps everyone has moments when they “somehow feel empty.” That’s exactly when I’d like you to listen to “Kara/Kyo (Emptiness/Void).” It’s a piece by Vocaloid producer Presto, created using Hatsune Miku.

The song centers on the two kanji in the title, expressing both “feeling hollow inside” and “the futility of life.” However, it isn’t gloomy—by the end, it points toward hope for the future.

Listening to it will surely lift your spirits.

prisonerPrisoner P

Prisoner [Inmate] - Kagamine Len
Prisoner Prisoner P

It portrays the tragedy of two people who should never have met, who do meet and are then torn apart—and that alone is enough to make you cry.

On top of that, the raised-pitch vocal quality unique to VOCALOID sounds like a pained scream, squeezing my heart.

I can’t believe this song is the author’s debut work.

Singing in the pouring rainshigure (late autumn/early winter drizzle)

Singing in the Pouring Rain / Ame Uta-ru
A sudden shower sings in the pouring rain.

“Singing in the Pouring Rain” is a work released by Shigure in November 2019.

It’s an original song written for the 10th-anniversary compilation album of Amau Utaeru, “EMERALD.” Its emotional, dramatic progression is captivating, giving the impression that feelings intensify as the song advances.

The lyrics, imbued with a sense of parting from a loved one, tighten the chest.

It’s a piece that makes you want to keep facing forward and moving on, even in the rain.

PuzzleStag Beetle P

Hatsune Miku Original Song 'Puzzle'
Puzzle Stag Beetle P

Included on the 2010 album “Flashback Sound.” From the intro, the weeping-sounding guitar melody really grabs me.

The contrast with the piano is beautiful too, fitting both a bittersweet state of mind and emotions on the verge of overflowing.

It feels like my feelings are about to undergo a gestalt collapse! The days I lost without noticing, and the days we laughed together—surely both are irreplaceably precious.

detoxrice straw bag

You’ll be drawn into a world shaped by Otomachi Una’s transparent, crystalline singing voice and distinctive sound design.

This work was released in April 2025.

PaletteYuyoyuppe

This is a masterpiece born from the collaboration of Yuyoyuppe and meola.

Waves of sound spread out over an intense synth-driven base.

Megurine Luka’s mature timbre and natural singing using the English library further elevate the atmosphere.

It was released in 2009.

Crybaby BoyfriendHONEY WORKS

[Kagamine Len · Hatsune Miku ┗|∵|┓] Crybaby Boyfriend [Original PV]
Crybaby Boyfriend HONEY WORKS

A heartrending song depicting the breakup between a crybaby boyfriend and a strong-willed girlfriend.

You can feel the time they spent together—smiling and crying while thinking of each other—coming through and touching the heart.

The way the two try to face a sad farewell with smiles is deeply poignant, and you can sense the love they have built up until now.