Saddest Songs Ranking [2026]

from Y to YJimii Samu P21rank/position

Hatsune Miku from Y to Y

An extremely famous Vocaloid song by JimmyThumbP.

It is the first work in the “Mr.

Y Trilogy,” which consists of songs featuring Hatsune Miku as the vocalist: “from Y to Y,” “Pierrot,” and “Calc.” Numerous related videos, including cover versions, have been posted, gaining widespread popularity.

Calc.Jimii Samu P22rank/position

Calc.

This is a Vocaloid song that gently stays by your side in the sorrow of heartbreak.

Created by JimmyThumb-P, a Vocaloid producer known for numerous hits like “from Y to Y,” it was released in September 2010.

The unforgettable parting is sung over a fast-paced band sound, resulting in something that really pierces the heart.

Before you know it, you end up empathizing with the protagonist and feeling tears well up.

Many popular singers have covered it, so if you’re interested, be sure to browse the videos.

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Cowardly Mont BlancDECO*2723rank/position

DECO*27 – Coward Mont Blanc feat. GUMI

When it comes to GUMI songs, this is the one! I’m sure many Vocaloid fans would agree.

This track, created by the Vocaloid producer DECO*27—who has also written many songs for famous artists—was released in 2010.

The lyrics candidly portray the protagonist’s emotional weakness: even though they were supposed to love that person, at some point they lost sight of their true feelings.

You can feel that pain coming through the music, and it tightens your chest.

There’s also a novel adaptation, which I highly recommend checking out as well.

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Unrequited loveAimer24rank/position

Aimer “Kataomoi” MUSIC VIDEO (FULL ver.)

“Kataomoi” captured many hearts with lyrics that portray deep affection and bittersweet longing.

It’s a popular song by Aimer that carries the wish to fall in love again, even after being reborn.

Many fans resonate with the lyrics, which sing that love in the heart doesn’t change, even if feelings are one-sided or appearances do.

The strong will to keep thinking of someone dear is truly moving.

Released on the 2016 album “daydream,” it’s a song we especially recommend to anyone carrying the ache of unrequited love.

It’s sure to become a source of comfort.

Happy Endingback number25rank/position

back number – Happy End (full)

Produced in November 2016 as the theme song for the film “My Tomorrow, Your Yesterday,” this piece portrays the poignant feelings of a woman who has decided to part ways.

Though her love remains, she suffers because she must leave the person she cares for.

Inside, the pain makes her want to cry, yet she puts on a brave face and pretends to be fine with a smile.

These complex emotions are expressed with delicate nuance.

Written and composed by Iyori Shimizu and co-arranged with Takeshi Kobayashi, the song reached No.

3 on the Oricon weekly chart and was certified Double Platinum by the Recording Industry Association of Japan.

It is a song that deeply resonates with those who, despite the pain of heartbreak, are trying to move forward, and with anyone who has experienced parting from someone dear.

moonlightOnitsuka Chihiro26rank/position

Chihiro Onitsuka – Gekkou (Moonlight)

When it comes to Chihiro Onitsuka, her signature song is “Gekkou” (“Moonlight”).

Released in 2000, it was her second single.

Many people may strongly associate it with the hit drama Trick, for which it served as the theme song.

It’s a ballad that deeply resonates with those whose hearts are tired—one that can move you to tears.

If you’re holding in your pain or sadness and can’t let it out, it might be good to let yourself sink all the way down with a song like this.

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First loveUtada Hikaru27rank/position

Hikaru Utada – First Love

A signature ballad by Hikaru Utada that conveys endless feelings for a parted lover through gentle piano and a crystal-clear vocal.

From the faint bitterness felt in a goodbye kiss flows the protagonist’s emotions—filled with the sadness and resignation of the one left behind.

Yet it’s not mere lingering attachment; there’s a realization that they learned “how to love” from the person they broke up with, and a quiet strength in accepting that this romance will forever hold a special place in their heart.

Released as a single from the March 1999 album First Love, it was used as the theme song for the TV drama Majo no Jōken (Forbidden Love).

It’s a song that gently embraces anyone who has someone they’ll never forget, or who keeps thinking of a former lover even after parting.

Fleeting eternityYasuha.28rank/position

［Eng Subs］Hatsune Miku – Ephemeral Eternity【Vocaloid Original Song】【Multilingual Subtitles】

A bittersweet love story spun on Miku’s singing voice.

Crafted by Yasuha.

and released in April 2023, it’s an R&B‑tinged ballad that gently accompanies those bearing the pain of heartbreak.

The fleeting memories of a fading love are portrayed through a soft melody and a transparent, pure vocal tone.

Immersing yourself in the emotion of how once‑happy times now feel like a burden makes your chest tighten.

This is a song that quietly stays by the side of your wounded heart.

Kurayasukoppu29rank/position

[Hatsune Miku Soft] Kuraiya [Original Song with PV]

When you start thinking about the meaning of life, it turns into a quagmire—you can’t get out of it, can you… This song is by the Vocaloid producer scOpe, known for works like “Irony” and “Keppekishou,” and it was released in 2013.

The tender piano tones gently wrap around the wistful band sound—its sound alone is enough to make you cry.

And of course, it’s the feelings woven into the lyrics.

You just want to be happy, and yet why does it hurt this much? It’s impossible not to empathize with that sentiment.

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366 daysHY30rank/position

HY – 366 Days (Official Music Video)

There may be many people suffering from lingering feelings of love that won’t fade even after a breakup.

This is a poignant ballad by HY, a band from Okinawa, known for being written by Izumi Nakasone based on her own experiences.

It vividly portrays the depth of love so strong you remember your ex’s scent and gestures, and the turmoil of an unattainable love—piercing straight to the heart.

The track was included on the album “HeartY,” released in April 2008.

At the time, it was used as the theme song for the film and drama Akai Ito, and became a major talking point.

It continues to be cherished, even serving as the theme song for a drama starting in April 2024.

On nights when your heart aches from an unfulfilled love, or when you just need a good cry, please give it a listen.