[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)
Sea Roar TrainKozakura Maiko
A song by Maiko Kozakura that portrays a heartrending love.
Set on a train journey along the Sea of Japan, it skillfully expresses the feelings of a protagonist carrying the pain of heartbreak.
Even while putting on a brave face, they are consumed by regret, and their resolve to win back love once more is deeply moving.
Kozakura’s emotive vocals beautifully convey the complex mix of sorrow and hope.
The overlap between the beautiful scenery unfolding outside the window and the protagonist’s wavering heart is also striking.
It’s a song that comforts those who wish to heal from heartbreak or seize another chance at love.
OH MY LITTELE GIRLOzaki Yutaka
It’s a famous love song by the one and only Yutaka Ozaki.
It has been used as the theme song for various works, including the film Hot Road.
Ozaki’s powerful vocals and straightforward lyrics really strike a chord.
It’s a masterpiece I hope you’ll listen to while thinking of someone you love.
cosmos (flower)Yamaguchi Momoe
Tomorrow I’ll leave my parents’ home and finally get married.
This is a classic wedding song sung from the daughter’s perspective, capturing that mix of joy and bittersweet emotion.
Even if marriage changes her last name, she’ll never forget her gratitude to the parents who raised her—there’s a strong bond you can feel.
One more time, One more chanceYamazaki Masayoshi
This song portrays the ache of continuing to seek a lost love and the longing for another chance.
Masayoshi Yamazaki released it in January 1997, and it was used as the theme song for the film “The Moon and a Cabbage.” His refreshing voice appeals quietly yet powerfully.
In 2007, it was also chosen as the theme song for Makoto Shinkai’s animated film “5 Centimeters per Second,” winning new fans as well.
Gently enveloping the pain kept in one’s heart, this work evokes the hurt of heartbreak and feelings for someone dear.
Many listeners will feel a tightness in their chest and find tears flowing naturally.
It’s a recommended track when you want to find a touch of hope or healing amid sorrow.
[Tearjerker] Heart-wrenchingly bittersweet and sad songs (201–210)
I’m home.Teshima Aoi
This song by Aoi Teshima, known for her signature tracks “Teru’s Song” and “Letter to Tomorrow,” was chosen as the theme for the drama “Heaven and Hell: Two Psychos.” Her greatest charm—her calm, breathy voice—alone can stir a poignant ache in your heart as you listen.
Looking closer at the lyrics, they depict through vivid scenes how a beloved person has suddenly disappeared from the room they once shared, making it feel all the more real and striking.
If you’ve been through something similar and are feeling fragile, this is a song I truly hope you’ll hear.
You’ll likely find many moments that resonate, and the tears will come naturally.
Why did I end up falling in love with you?Tōhōshinki
This is the eighth single released by Tohoshinki in 2008.
As the straightforward title suggests, it sings about the feelings of seeing an ex-lover get married.
Even if you were very happy while you were together, those memories can become painful after a breakup—it’s something that happens.
Heartache takes time to heal, but it’s something we’d like to cherish as a good memory in the end.
I miss youHayashibe Satoshi
Tomofumi Hayashibe, who made his debut thanks to an audition show, released his first single “Aitai.” It’s a ballad that expresses feelings for a precious person one can no longer meet.
Since the specific situation isn’t clearly stated, it’s a song that’s easy to relate to your own experiences.
Also pay attention to his conversational singing style and high-tone voice.
The sound itself is soothing.
And if you like it, there are multiple versions available, so try comparing them.
