Heisei-era heartbreak songs: A roundup of classic tracks from the ’90s to the 2010s
From around the 1990s through the 2010s, countless timeless songs were released in the Heisei music scene.
Among them were many heartbreak songs, and I’m sure many of you have been listening to them ever since they first came out.
In this article, we’ll introduce a wide selection of those Heisei-era heartbreak songs all at once.
We’ve chosen tracks that carry a nostalgic feel—ones that will bring back memories from those days when you listen.
If you lived through that era, please enjoy them while reminiscing.
And if you’re from a younger generation and didn’t experience that time, we encourage you to take your time listening while reading the lyrics.
- Breakup songs that were hits in the 2000s
- A heartbreak song that was a hit in the 90s. Classic and popular tracks in Japanese music.
- Emotional songs from the Heisei era. Nostalgic tracks that really hit you.
- Tear-jerking J-pop from the ’90s. Hit songs and real tearjerkers.
- Breakup songs sung by male artists that I’d recommend to Gen Z
- [Heisei Love Songs] A carefully selected collection of gem-like love songs that continue to be cherished even in the Reiwa era!
- [Female Heartbreak Song] A soul-stirring song dedicated to you, who loved with all your heart.
- [Heisei Songs] Classic hits from the Heisei era that are popular on Instagram Reels
- Tears won’t stop with these sentimental lyrics! Heisei-era tearjerker songs
- [Tearjerker Guaranteed!] A Heartbreak Song Told from a Male Perspective
- My heart aches with bittersweet pain! Breakup songs I’d recommend to Gen Z
- Just listening makes my chest tighten... Breakup songs recommended for the Yutori generation
- Recommended breakup songs by male artists for the Yutori generation
Heisei-era heartbreak songs: A roundup of classic tracks from the ’90s to the 2010s (21–30)
tobacco / cigarette(s)Koresawa
A singer-songwriter beloved for relatable, down-to-earth lyrics, Koresawa delivers a piercing song of regret.
The protagonist is portrayed desperately trying to recover the warmth of lost days from the small personal items their partner left behind.
The depictions of miscommunication—“If only I’d paid more attention to them,” “If only they had cared more about me”—will resonate painfully with anyone who has parted ways with a long-time partner.
Released in March 2017, this work is marked by its acoustic sound.
For those who feel their own shortcomings led to the breakup, this song may quietly sit with you and allow you to shed your tears.
366 daysHY
This is a ballad about the lingering feelings of being unable to forget a lost love.
Included on HY’s 2008 album “HeartY,” the song was used as the theme for Fuji TV’s drama and film “Akai Ito.” Its gentle melody, highlighted by a memorable piano line, carries lyrics that reflect on the memories of a lover who remains in the heart.
The duet version by vocalists Izumi Nakasone and Hideyuki Shinzato is also captivating, with the interplay of male and female voices bringing out the nuances of emotion even more vividly.
It’s a recommended track for those who have experienced parting with someone dear or are trying to overcome the pain.
Never again…BENI
This is a ballad with an R&B-style melody, marked by a poignant blend of piano and strings.
The transparent, airy vocals delicately express emotions swaying between lingering feelings for a former lover and the reality that there’s no going back.
Released in December 2008, it’s BENI’s ninth single and was used as the ending theme for the music program “Hz.” Created as an answer song to Dōzi-T’s “Mou Ichido… (One More Time…),” it’s said that BENI herself shed tears during the music video shoot.
It’s a song that will gently stay by your side on nights when you want to wash away your sorrow with tears.
Don’t forget.DREAMS COME TRUE
This is the 10th single by DREAMS COME TRUE, released in October 1991.
It was also included on the album MILLION KISSES, released the following month, which became a huge hit and was certified 2× Million by the Recording Industry Association of Japan.
The lyrics dwell on lingering feelings for a former lover, and the heartfelt plea—“Even if you hate me, please don’t forget me”—is deeply moving.
It’s a ballad that gently wraps the pain of parting.
beetle (specifically, a rhinoceros beetle)aiko
It’s a song by aiko that portrays a delicate heart: identifying with an insect that protects itself with a hard shell yet is fragile inside, and acting tough precisely because it’s in love.
Like that insect that cannot survive the winter, the song foresees the end of love, yet its deep affection moves you as it tries to accept even the sadness as a cherished memory.
Released in November 1999, it was also used as the ending theme for TBS’s CDTV.
If you’ve ever found yourself putting on a brave front in front of someone you like, you’ll understand this all too well! As you listen, may you embrace that awkwardness as a part of yourself and find the courage to step forward into tomorrow.