Saddest Songs Ranking [2026]

Amanojaku1641rank/position

Amano Jakku / 164 feat. GUMI (Official)

The heart-piercing, bittersweet lyrics really sink in.

If I confess, we might never be able to go back to being just friends.

It’s a painful, sour song about the flutter of unrequited love and the struggle of constantly lying to my own feelings.

GUMI’s voice sounds forlorn, as if wrung out to the very last drop.

Patchwork Staccatotoa2rank/position

Toa – Patchwork Staccato – ft. Hatsune Miku

It’s a bittersweet Vocaloid song that sings, “If we only seem connected but really aren’t, then I’d rather not be connected at all.” It’s a work by Vocaloid producer Toa, also known for “Music Music” and “Puzzle Girl,” released in 2014.

The crisp sound arrangement might come off as cute at first, but combined with the lyrics it takes on a somewhat fragile tone.

The clear, translucent vocals are memorable as well.

It’s a Vocaloid track you’ll want to sit with and listen to carefully when you’re alone.

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Araki Jakkan

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Happinessback number3rank/position

Happiness / back number (cover)

Back number is a rock band beloved by listeners for their love songs told from every perspective.

Among their tracks, “Shiawase” portrays a heartrending unrequited love.

It was included on the 2011 single “Hanabira.” The song is a grand ballad, its poignant yet warm piano sound resonating throughout.

The lyrics express the feelings of loving someone even while knowing they can never be your partner.

Many will relate to the words, which speak directly with a pure sentiment.

It’s a song that deeply moves the heart with its wish for the other person’s happiness, even without being rewarded.

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mutō

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PretenderOfisharu Higedan Dism4rank/position

Official HIGE DANDism – Pretender [Official Video]

This is one of Official HIGE DANDism’s signature ballads, sung over a dramatic melody about the end of a heartrending love.

The protagonist deeply loves the other person yet realizes they are not meant to be, and their inner struggle is heartbreaking.

Holding an impossible wish—if only in another timeline—and ultimately stepping back while praising the other’s beauty, the lyrics are impossible to hear without tears.

Released as a single in May 2019, it became widely known as the theme song for the film “The Confidence Man JP.” Pouring your feelings into it at karaoke will surely lighten the burden on your heart.

A song that heals the pain of heartbreak and helps you gradually look forward, this masterpiece gently stays by your side in the season of farewells.

Don’t go.Souta5rank/position

Uta-nee Yuki “Don’t Go” (remaster)

The true feelings you can’t bring yourself to say… hasn’t everyone experienced that? This is a signature song by Vocaloid producer Souta, released in 2013.

Its somewhat retro-sounding arrangement pairs perfectly with Yuki Kaai’s softly murmuring vocals.

It somehow makes you feel nostalgic.

The lyrics portray the protagonist’s inner thoughts at the moment of parting with someone precious.

As the title suggests, they want to say “Don’t go,” but can’t bring themselves to say it… It’s a tear-jerking Vocaloid track that makes you imagine all sorts of stories—what might have happened between these two, and more.

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Araki Jakkan

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to liveMizuno Atsu6rank/position

Live (feat. KAFU) – Atsu Mizuno

Set to a calm piano melody, this delicate piece candidly expresses the struggles and conflicts of life.

Released by Atsu Mizuno in July 2021, it exists in two versions: one sung by the artist themself and another sung by the VOCALOID character Kafu.

Carefully portraying the feelings of a protagonist who shies away from society’s expectations and love while still possessing the strength to believe in their own potential, the song resonates with those who, despite carrying their own weaknesses and anxieties, strive to find meaning in living.

Its poetic imagery—seeing the stars in the night sky and the light of the moon as proof of one’s existence—is also noteworthy.

PrologueUru7rank/position

[Official] Uru “Prologue” Premium Studio Live

Sung by Uru, “Prologue” is a heartbreaking song about unknowingly searching for an unattainable love.

Released as a single in 2018, it was chosen as the theme song for TBS’s Tuesday drama “Chugakusei Nikki” (Diary of a Middle School Student) and reached No.

1 on Billboard’s download chart.

The lyrics perfectly match the drama’s story, which portrays a forbidden romance between a teacher and a student.

It’s a song I’d love for students who’ve found themselves falling for a teacher—or teachers who’ve fallen for a student—to listen to.

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Hamada Takuya

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