[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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[Tearjerker] Songs so heartrending and sad they make your chest tighten (171–180)
I can’t put it into wordskurisu haato
Chris Hart, an American-born singer who debuted in Japan in 2013, has since acquired Japanese citizenship and has truly become a Japanese singer in both name and reality.
His 2016 release “Kotoba ni Dekinai” is a cover of Kazumasa Oda’s classic hit.
Hart’s uniquely soaring vocals bring out new value in the song.
Maplesupittsu
It’s one of Spitz’s signature songs and absolutely essential when introducing bittersweet tracks.
Although it was released in 1998, it has been used multiple times as a TV drama theme and in commercials, so many younger listeners are familiar with it.
The lyrics convey a heartfelt longing for a beloved person who is no longer here, and it really tightens your chest.
Masamune Kusano’s soft, gentle vocals and the warm, quintessentially Spitz instrumentation have a soothing effect, yet at the same time they heighten the poignancy embedded in the lyrics.
far; distant; by farsupittsu
It’s the 23rd single released by Spitz in 2001.
A fantastic world unfolds, drawing listeners into another dimension.
You could call it a love song, and you could also hear it as New Age-style rock.
The endlessly heartrending lyrics bring you to tears.
Hyperventilation LoveTonbokōpu
Tonbocorp is a four-piece rock band whose genre-defying sound has been generating buzz, especially on social media.
Their song ‘Kokyūai’ (‘Hyperventilating Love’) from their first mini-album ‘Uka’ (‘Eclosion’) was selected as the opening theme for the TV drama ‘Yawao to Katako’.
The lyrics evoke the image of someone regretting an irrevocable relationship yet drawing a line and trying to move forward, making your chest tighten with that unrequited feeling.
It’s a lyrical rock tune whose poppy, light-footed melodies and ensemble only heighten the sense of melancholy.
Blueberry Nightsmakaroni enpitsu
The bittersweet breakup song “Blueberry Nights” was apparently written by Hattori, the vocalist of Macaroni Enpitsu, with his ex-girlfriend in mind.
It portrays a woman who can’t give up on him, wavering between her love and the resolve to move on.
It’s incredibly painful when, at the moment of parting, one person has no feelings left while the other still holds deep affection.
For those who are carrying the weight of such a sad breakup, listening to this song might help them feel a bit more positive—thinking, “There are others suffering like this too; I’m not alone!”
[Tearjerker] Songs so heartrending and sad they make your chest tighten (181–190)
the absolute worstMarushii
After breaking up with a partner, some people may find themselves overwhelmed by a complicated mix of emotions.
A song that might give voice to those feelings is “Saitei Saiaku” (“The Absolute Worst”).
It’s a track released by the three-piece rock band, Marcy.
The lyrics express both intense anger toward an ex and the waves of sadness that well up from time to time.
It’s a piece where ineffable emotions feel captured within the music itself.
That said, it has a driving, fast-paced feel, so it’s also a great pick when you want to lift your spirits.
powder snowRemioromen
Although some time has passed since its release, this is still a hugely popular karaoke classic and a standout ballad.
It’s a massive hit by Remioromen, a three-piece rock band from Yamanashi Prefecture, released in 2005 as their eighth single.
After being featured as an insert song in the drama “1 Litre of Tears,” it reached a wide audience.
Above all, the chorus is searingly passionate—the vocals cut deep, as if laying bare every feeling in the heart.
It’s a quintessentially bittersweet song that you’ll want to listen to in winter.
