[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 (51–60)
Cinderella BoySaucy Dog
When it’s hard to get over heartbreak, music can give you strength, right? “Cinderella Boy” is a poignant number that puts into words the indescribable feelings between lovers.
Released in 2021 by the rock band Saucy Dog, its music video—told through illustrations—is striking.
Warm guitar tones melt into the mid-tempo track, moving listeners deeply.
The lyrics vividly depict small, everyday moments, making it impossible not to relate.
It’s a song that resonates with anyone carrying an inexpressible sorrow.
Because you are hereUru
Speaking of Uru, she’s a singer-songwriter known for uploading vocal performance videos of various songs to her YouTube channel even before her debut.
She has released many wonderful tracks such as “Prologue” and “Kiseki,” but it was “Anata ga Iru Koto de” that brought her breakthrough.
The song was chosen as the theme for the drama “Theseus no Fune.” Many listeners were deeply moved by the lyrics, which resonate with the story’s depiction of bonds with loved ones.
It’s a gentle ballad, yet her overwhelming vocal prowess gives the piece a powerful emotional impact.
Lostyama
A song filled with bittersweet sorrow that portrays the painful inner struggle of living while bound to joyful memories with a loved one.
It’s a track by yama, featured as an insert song in the film “The Lines That Define Me,” starring Ryusei Yokohama.
Many of us have experienced despair at a present that won’t move the way we wish, even when we know there’s no going back, and we can’t help but cling to the past.
Memories we want to forget yet don’t want to let go—doesn’t everyone carry one or two of those in their heart?
Tokyokinoko teikoku
As the lyrics say, it’s a lonely song that feels like spending a Sunday all by yourself.
It tenderly sings about the small hurts and moments of happiness found in everyday life.
Though it’s titled “Tokyo,” I hope people who don’t live in Tokyo will listen to it too.
[So Moving It Brings You to Tears] Songs So Bittersweet and Sad They Make Your Chest Tighten (61–70)
Everyday Revolutionneguse.
On long nights spent facing a breakup—or when you’re looking for an outlet for feelings you’ve tucked away—Neguse’s “Nichijou Kakumei” (Everyday Revolution) is just what you need.
Released in September 2022, this song’s warm melody and lyrics pierce deeply into the listener’s heart.
It opens with recollections of happier days and gradually shifts toward the sorrow of lost love.
With fresh, vivid emotion, it traces how small changes in everyday life can lead to a heartbreaking farewell.
In the music video, memories flash by like a revolving lantern, emotionally portraying the loneliness of joyful times slipping away.
The blend of tenderness and sadness in this song will loosen your tear ducts before you know it.
Sakura Lovemosao.
Singer-songwriter Mosawo, who sings love songs from a woman’s perspective and has been gaining empathy and attention.
Her new work “Sakura Koi” was created based on stories from high school girls.
Many tales of unrequited love were sent to Mosawo, and she wove those words into the lyrics.
Because it’s grounded in real experiences, you can truly feel the ache in your chest.
The melody, overflowing with wistfulness, also draws you in and lets the lyrics sink in effortlessly.
You’ll likely find parts that overlap with your own experiences, so let yourself cry your heart out.
If I were to die tomorrowKitanitatsuya
This is a moving song that weaves together wistfulness and hope around the theme of one’s final day in life.
Tatsuya Kitani’s delicate vocals ask what and who you would think of if tomorrow were your last.
Included on the album “roundabout,” released in January 2024, it carries a message that resonates deeply with listeners.
For those of us who get caught up in daily life and tend to lose sight of what truly matters, it teaches the importance of cherishing the present moment.
It’s a song I especially recommend to anyone who has experienced heartbreak or parting and feels lost in life.
Through this work, you’ll be prompted to reflect anew on the meaning of living and on the values we should hold dear as human beings.