[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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[Tearjerking] Songs so heartrending and sad they make your chest tighten (111–120)
Tears of the MagnoliaSutaadasuto Rebyuu
From the perspective of someone left behind, “Mokuren no Namida” is a song that sings of unforgettable memories.
It was released by Stardust Revue in 1993, and its lyrics have resonated with many people.
The song is rich with various metaphors, so I hope you’ll take your time listening to it.
It’s also known for being covered by many artists, including Shigeru Matsuzaki.
In addition, there’s a version featuring Kobukuro, which is a must-listen as well.
[Tearjerker] Songs so heartrending and sad they make your chest tighten (121–130)
MissingKubota Toshinobu
This is a track from Toshinobu Kubota’s first album, released in 1986.
It’s a wistful love song with the soulful vibe characteristic of Kubota’s style.
The expressions of morning and night are very poetic, and I find it romantic to view love in this way.
lampSakiyama Soshi
The ending theme for the second season of the anime Jujutsu Kaisen is Soushi Sakiyama’s “Hi.” Released as a single in 2023, it was reportedly crafted to capture feelings toward the character Suguru Geto.
While it has a pop sound, the track is infused throughout with Sakiyama’s distinctive sensibilities.
The lyrics, which poignantly express the sadness and sense of loss when something you took for granted turns out not to be so, are especially striking.
Definitely give it a listen!
Even if I’m not there.Hirai Dai
When it comes to epic love songs filled with thoughts for one’s future family, “Even If I’m Not There” comes to mind.
Released in 2022 by singer-songwriter Dai Hirai, who delivers refreshing tracks that evoke the seaside and sandy beaches, it offers a warm yet bittersweet message to beloved partners and children that truly tugs at the heart.
The beautiful, soothing sound centered on strings and piano is equally captivating.
It’s a song that overflows with gratitude for the precious people by your side right now.
Be sure to listen for his gently resonant vocals that sink into the soul.
#302Hirai Ken
The song chosen as the theme for TBS’s Friday drama “4-Minute Marigold,” which centers on a searing, all-consuming love, is Ken Hirai’s 46th single, “#302,” released in 2019.
It’s a love ballad, arranged primarily with acoustic guitar, that matches the drama’s tone.
The lyrics portray “me” staying close to “you” after a heartbreak, and combined with Hirai’s vocals, they evoke an achingly bittersweet feeling.
Thinking of youMatsushita Kohei
Amid the many heart-stirring songs that take heartbreak and parting as their themes, Kohei Matsushita’s “Kimi o Omou” stands out.
The gentle piano melody and the poignant strings strike a chord, quietly staying close to the listener’s heart.
The song speaks of that bittersweet feeling of being more than friends but not quite lovers.
Its delicacy resonates with many people’s experiences and evokes empathy in those carrying a quiet ache.
His warm voice sinks deep into the heart, offering a soft source of strength in difficult times.
It’s truly a recommended track for releasing your emotions.
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.
