[So touching it makes you cry] A heartbreakingly wistful and sad song that tightens your chest
A feeling like your chest is being tightly squeezed…
Heartbreak, parting from someone precious, the daily pains…
Here are some heartbreaking songs that will bring tears to your eyes when you listen.
We’ve gathered tracks for those who want to have a good cry or be comforted by songs that share the same feelings.
From timeless classics to the latest releases, we’re covering a wide range—so be sure to read to the end.
Even with sad songs, finding ones you can relate to helps you realize you’re not alone.
By the time you finish listening, your sadness and heartache might just turn a little more positive.
Let these wistful songs guide you, and allow yourself to honestly let out your weakness and pain as your emotions lead you.
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[Tearjerkers] Songs so heartrending and sad they make your chest tighten (191–200)
White LoversKuwata Keisuke

This is a song that offers comfort to those who have experienced a breakup.
Released by Keisuke Kuwata in 2001, it delicately portrays the sorrow of walking alone through a snowy town.
Chosen for a Coca-Cola commercial, the piece moved many listeners, winning a Japan Record Award Gold Prize and becoming a major hit with 520,000 copies sold in its first week on the Oricon weekly chart.
It’s best enjoyed on a quiet winter night while gazing out the window.
Let yourself be wrapped in its heartwarming melody, which beautifully evokes memories of a love that has passed.
I won’t fall in love anymore.Makihara Noriyuki

We often hear stories like, “Only after someone is gone do you finally realize how precious they were.” In Noriyuki Makihara’s smash hit ‘Mou Koi Nante Shinai’ (“I Won’t Love Again”), the feelings of a man who can’t help but regret are depicted as he realizes that life was fun and comfortable precisely because his partner was there in his everyday life.
Few people probably think, while their partner is still by their side, about what it would be like if they were gone.
But when you listen to this song, many will likely feel inspired not to take day-to-day moments for granted and to appreciate the person who spends those moments with them.
beloved personShio Reira

A song filled with heart-stirring poignancy.
Leira Shio’s gentle yet powerful vocals leave a strong impression.
It’s a heartbreaking love song that portrays two people drifting apart because of their different ways of expressing love.
Included on the first EP “No one” released in August 2024 and used as BGM for the dating reality show “Kimi to Ookami-kun ni wa Damasarenai,” this track is recommended for those who’ve experienced heartbreak or a breakup, or who are struggling with their current relationship.
Why not listen to this song and honestly embrace the complex emotions within you? You’ll surely discover something new.
HANABI ~episode Ⅱ~Hamasaki Ayumi

It’s a number that brings a rush of bittersweet fragility to the heart, vividly portraying feelings of a love that scatters beautifully like fireworks.
Included on the single “&,” released in July 2003, it’s a perfect song for those carrying the pain of heartbreak or lingering attachment to the past.
Ayumi Hamasaki’s translucent vocals and the gentle melody provide comfort to listeners.
It’s recommended for moments when you want to look back on wistful late-summer memories or when you’re trying to overcome a farewell with someone important.
[Tearjerker] Heart-wrenchingly bittersweet and sad songs (201–210)
It hurts.Kiyoshi Ryujin

This is a single released in 2010 by singer-songwriter Ryuji Kiyoshi.
The song moves from piano-centered sounds into a grand, expansive atmosphere that truly stirs the heart.
While it can be seen as expressing the pain of unrequited love, the fact that the lyrics never explicitly state this makes it feel more like an expression of deeper, inner hurt.
The meticulous portrayal of feelings toward the person they love and the strained, wrung-out vocals make it a track that feels like an outpouring of emotional anguish.
PerfumeEito

This is the song that triggered Eito’s breakthrough and can be considered his signature track.
It was born almost improvisationally during a session with friends, so the accompaniment is kept simple with just an acoustic guitar.
Precisely because there are so few instruments, you can really savor the vocals and the lyrics.
The lyrics are based on Eito’s real experiences, expressing the emotions tied to them—a heartrending breakup song.
Scents can act as triggers that bring back memories; at times, they can also lead to pain.
periodIshizaki Hyuui

Sung by singer-songwriter Huwie Ishizaki, this song portrays heartbreak and lingering attachment from a male perspective.
The lyrics include scenes that evoke the fun times the couple once shared, yet they’re interwoven with many lines where he tries to tell himself she’s no longer there.
Listening to it makes your chest tighten more and more.
Surely, many of us have struggled to force ourselves to forget an ex we once loved.
It’s a song that will tug at your heart as it overlaps with your own experiences.



