RAG MusicHeartbreak Songs
A wonderful heartbreak song

[2026] Recommended for Men in Their 40s! A Collection of Classic Japanese Breakup Songs

When you go through a heartbreak, it can feel like there’s a gaping hole in your heart.

Little moments can bring those memories rushing back, leaving you with a pang of sadness.

In this article, we’ve gathered Japanese breakup songs released from the 1990s to the mid-2000s—the soundtrack to the youth of those who are now in their 40s.

The nostalgic melodies you used to listen to back then and the lyrics that resonate in your chest may hit even deeper now.

As you look back on past loves, why not find a small push to move forward, together with these timeless songs that stay close to your heart?

[2026] Recommended for Men in Their 40s! A Collection of Classic Japanese Breakup Songs (11–20)

Crimson-colored sunsetFujifaburikku

A heart-wrenching ballad lovingly passed down since their indie days.

It resonates deeply with a lyrical melody, capturing the tangled feelings toward one’s hometown and the earnest resolve to face forward even while carrying the weight of everyday struggles.

After being included on the 2004 album “A la Mode,” the song was released as their sixth single in September 2005 and was also chosen as the ending theme for TV Kanagawa’s “saku saku.” It appears on classic albums such as “FAB FOX” as well.

Following the sudden passing of Masahiko Shimura, Tamio Okuda covered the song in a solo acoustic performance, famously singing it through tears.

When you want to reflect alone at dusk on past loves or your youth, this song is sure to offer gentle companionship.

OverMr.Children

It’s a heartbreak song with strong fan appeal, included on the 1994 album “Atomic Heart.” Rather than depicting a dramatic breakup scene, Kazutoshi Sakurai—who wrote both the lyrics and music—captures the cruel reality of “love’s end” that confronts you in an ordinary, fleeting moment.

The way the protagonist recognizes, from shifts in the other person’s expressions and behavior, that there’s no room left for him feels painfully real, and Sakurai’s vocals amplify that poignancy.

It’s harder to be presented with the cold, undeniable truth than to be dumped without knowing why.

For those who’ve been there, it’s a song that revives a bitter ache, yet somehow also stirs a sense of nostalgia and optimism—a true classic.

I won’t fall in love anymore.Makihara Noriyuki

[Official] Noriyuki Makihara “I Won’t Fall in Love Again” (Music Video) [5th Single] (1992) Noriyuki Makihara / Mou Koi Nante Shinai
I won't fall in love anymore.Makihara Noriyuki

It was released in 1992 as Noriyuki Makihara’s fifth single.

Chosen as the theme song for the Nippon TV drama “After the Children Go to Sleep,” it became a million-selling hit.

After hearing a friend’s story of heartbreak, Makihara created the song with the hope of making something uplifting to help heal a broken heart.

It remains one of his most popular and representative songs.

Blue BenchSasuke

Released in 2004 as their major-label debut single, this is Sasuke’s signature song that still brings many men to tears.

The setting is a long-awaited class reunion: the person you once loved is there with the same unchanged smile.

Along with the nostalgia comes a surge of fierce regret toward the “you of back then.” Sasuke’s unadorned, down-to-earth harmonies speak for those sweet yet bittersweet feelings in your heart.

Even though there’s no point in thinking “if only, back then…,” the pain of youth resurfaces in unguarded moments.

It’s a masterpiece packed with that lingering male heartbreak, one that conjures up the scenery of those days every time you listen.

Can’t Say Anything… SummerTHE JAYWALK

[Official] J-WALK “Speechless… Summer”
Can't Say Anything... SummerTHE JAYWALK

Released in 1991 as J-WALK’s 18th single, it sold about 980,000 copies and became one of the band’s signature songs.

Thanks to its success, they made their first appearance at the 44th NHK Kōhaku Uta Gassen in 1993, and it became their biggest hit.

Known as a bittersweet summer song, it remains a popular choice for karaoke.

One more time,One more chanceYamazaki Masayoshi

Masayoshi Yamazaki – “One more time, One more chance” MUSIC VIDEO [4K Quality]
One more time,One more chanceYamazaki Masayoshi

Released in 1997 as Masayoshi Yamazaki’s fourth single, this is a classic that represents the 1990s.

Chosen as the theme song for his first starring film, The Moon and the Cabbage, it became a long-running hit and one of the signature songs from the early part of his career.

Its poignant lyrics, which convey the sorrow of heartbreak and the pain of losing someone dear, are especially memorable, making it a timeless breakup anthem passed down across generations.

[2026] Recommended for men in their 40s! A roundup of classic Japanese heartbreak songs (21–30)

Only You ~Summer Heartbreak~Sazan Ōrusutāzu

Only You ~Summer Heartbreak~ [2024 Remaster]
Only You ~Summer Heartbreak~Sazan Ōrusutāzu

A poignant classic that colored the summer of 1995.

This exquisite heartbreak ballad portrays lingering feelings for a summer romance that has ended, set against the backdrop of a beautiful seaside scene.

Released as a single in July 1995, it became a major hit as the theme song for the drama “Itsuka Mata Aeru” (Someday We’ll Meet Again).

It was later included on the acclaimed album “Young Love,” and has become a special number—so much so that Keisuke Kuwata has called it “one of my favorite songs” among his own works.

The rich, weighty sound and Kuwata’s voice, which gives full voice to helpless, aching emotion, truly resonate in the heart.