Saddest Songs Ranking [2026]

two peopleaiko85rank/position

aiko - “Futari” music video

Despite its upbeat, fast-paced pop melody, this aiko classic grips the heart with a piercing, aching sadness.

Released as a single in March 2008, it’s also included on the acclaimed album “Himitsu.” In 2014, it was featured in a commercial for Hoyu’s BeautyLabo Whip Hair Color, leaving a lasting impression on many listeners.

The song portrays the frustration of knowing in your head that you shouldn’t fall in love, while your heart can’t keep up.

The bravado of telling yourself you’re glad you realized it before getting in too deep, and the vivid imagery of the Ferris wheel in the background, are sure to cut to the core of anyone suffering from an unrequited love.

Precisely because of its bright sound, it brings even more tears—making it a track you’ll want to listen to on nights when you’re burdened with feelings you can’t do anything about.

Reach for the SkyKasamura Tōta86rank/position

Reach for the Sky　/ feat. GUMI

Tota Kasamura, who has produced many piano ballad Vocaloid songs.

The piece he created using GUMI entirely in English is “Reach for the Sky.” This song portrays a woman who throws herself into the sea.

The scenery as seen from the ocean floor is depicted as both beautiful and cruel.

Try listening while substituting the sea and stones mentioned in the lyrics with various other things.

Also captivating is the richly expressive singing achieved with GUMI.

Every single word of the lyrics is filled with emotion.

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yamamoto

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orionYonezu Kenshi87rank/position

Kenshi Yonezu – Orion, Kenshi Yonezu

Kenshi Yonezu, who has crafted numerous heartrending love ballads, also created this song, “orion,” one of the most popular numbers among his love songs.

It’s also known as the ending theme for the anime March Comes in Like a Lion.

A love song themed around the winter constellation Orion, it conveys the chill of winter air, deepening the sense of melancholy.

Even if the love is unrequited, you find yourself wishing toward the sky—your chest tightens with the urge to entrust your hopes to God or the stars.

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utatane

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bamboo-copterKasamura Tōta88rank/position

Taketombo / feat. Vocoflex

A heartrending melody and lyrics that leave a deep mark on the heart.

It’s a song by Tota Kasamura, released in May 2024.

The feelings of someone who has gone through a breakup are portrayed with delicate nuance.

The gentle tones of the piano and the strong, resonant vocals create a harmony you can’t help but be absorbed in.

And the repeated words “It’s okay”…

it truly shakes the soul.

Of course, it’s wonderful to listen to yourself, but if you have a friend who’s struggling, sending it to them might just help.

First loveUtada Hikaru89rank/position

Hikaru Utada “First Love” (Short Version)

It’s a striking song that starts abruptly with Hikaru Utada’s vocals, without any prelude.

Whether it’s the chorus or the build-up to it, every part of the track conveys a sense of poignancy.

The lyrics vividly express the sadness and pain of first love.

The intricate melodies—ones that only Hikaru Utada could write—also speak to the complexities of love, making the wistfulness all the more palpable.

The end of lovemafumafu90rank/position

It’s the End of Love / Mafumafu [Music Video (Drama ver.)]

A song by Mafumafu, the singer-songwriter also known from the musical unit After the Rain.

It tells the story of a bittersweet love: going to a summer festival with someone you like, but lacking the courage to confess and letting it end there.

I’m sure many people have had a similar experience.

The lyrics are packed with delicate, true-to-life feelings, like memories of a fleeting love from school days.

If you’ve ever given up on a crush at a festival, please give it a listen.

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sasashina

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#302Hirai Ken91rank/position

Ken Hirai '#302' MUSIC VIDEO

Ken Hirai, a singer with a captivating husky high-tone voice, is known for his many popular love songs! In these lyrics, the protagonist has feelings for a woman who has just had her heart broken.

The song depicts the two of them going to karaoke together, and it’s truly moving.

That’s because, while he feels it’s unfair to be kind to her when she’s vulnerable, he still wants to be her support—an expression of love from the bottom of his heart.

If you’re wondering what to do when the person you like has just gone through a breakup, maybe treating them gently, as in these lyrics, could be one way to go.

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Hane Keisuke

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