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 Compilation of Classic Japanese Breakup Songs (101–110)

Swan songKinKi Kids

This is a single by KinKi Kids, popular for their overwhelming vocal ability and performances.

The highly narrative lyrics have been highly praised, depicting the pain of heartbreak in a descriptive way.

Its driving melody makes it a beloved heartbreak song among fans.

The Way Back to the FutureKobukuro

Kobukuro – The Road Back to the Future
The Way Back to the FutureKobukuro

A track included on an album by the hit-making duo Kobukuro.

Beloved for their relatable lyrics, this hidden gem is especially popular among Kobukuro fans.

With a universally appealing melody, it’s a well-liked song that expresses regret over being separated.

missingKubota Toshinobu

Toshinobu Kubota – Missing [Official Video]
missingKubota Toshinobu

A massive hit ballad by Toshinobu Kubota, one of Japan’s premier R&B singers.

This soulful love ballad is a classic that has been cherished by many for years.

With lyrics that speak for a man’s feelings after a breakup and a musical style rich in Kubota’s signature, jazz-tinged sensibility, it’s a masterpiece track.

I’m glad I met you.Koizumi Kyoko

Kyoko Koizumi – I'm Glad I Met You (Official Video)
I'm glad I met you.Koizumi Kyoko

When it comes to Kyoko Koizumi’s breakup songs, the first one that comes to mind is “I’m Glad I Met You.” Both the melody and the lyrics are heartrending, and it’s a ballad that men will likely find easy to sing.

It’s also got a good groove, making it a great choice for karaoke.

Graduationsaitou yuki

Yuki Saito “Graduation” MV
Graduationsaitou yuki

As a top idol of the 1980s, Yuki Saito captured the hearts of men everywhere.

Her song “Sotsugyo” (Graduation) is a heartbreak tune that sings of parting from someone you loved and setting off on a new journey.

It’s a nostalgic track that strongly evokes the Showa era.