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
- Guaranteed Tearjerker for Men! Japanese Breakup Songs Depicted from a Male Perspective [2026]
- 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)
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.
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.
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.
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.
Flavor Of LifeUtada Hikaru
This is a masterpiece that delicately portrays the bittersweet pain of heartbreak and parting.
Released in February 2007, it’s a song by Hikaru Utada and served as the image song for the TBS drama “Boys Over Flowers 2 (Returns).” It beautifully expresses the many emotions brought on by saying goodbye to someone you love, with a memorable melody that resonates as if you can feel the very essence of love throughout your whole body.
The song topped the Oricon Weekly Singles Chart for three consecutive weeks and was also included on the album “HEART STATION.” It’s a track that resonates deeply during the poignant moments of love or when you’re feeling uncertain about a relationship with someone important.
SakurazakaFukuyama Masaharu
A timeless masterpiece that gently cradles the feelings of a lost love, overflowing with bittersweet longing and tenderness.
Its sweet melody and emotionally rich vocals weave a heart-stirring love ballad that portrays a love unchanged even after a farewell.
Released in April 2000 as Masaharu Fukuyama’s 15th single, it was chosen as the theme song for the “Mirai Nikki V” segment of TBS’s “Unnan no Hontoko!” and ranked second on Oricon’s annual singles chart that year.
Healing hearts and resonating with many throughout the year, this song is perfect for the spring season.
While carrying the pain of parting, it conveys a pure wish for the other person’s happiness—an exquisite love song to listen to during spring’s farewells and new encounters.
The Continuation of TearsKahara Tomomi
It’s a heartfelt ballad that captures the sorrow of an adult heartbreak.
It portrays a woman who has gone through a devastating breakup and, having overcome the pain, now looks back on the past with calm reflection.
It’s not merely sad; the strength to smile as she recalls the memories and the sense of gratitude toward her former partner come through and are deeply moving.
Released in May 2005 to mark Tomomi Kahara’s 10th anniversary since her debut, this was her 24th single and a lead release from the album “NAKED.” It was also used as the ending theme for TV Tokyo’s drama series “Wednesday Mystery 9,” so some listeners may find it familiar.
This song gently supports those who are trying to move forward after a painful relationship.
Listening alone on a quiet night, it seems to teach us that even painful experiences will one day turn into cherished memories.