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[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 roundup of classic Japanese breakup songs (91–100)

Rainy BlueTokunaga Hideaki

Hideaki Tokunaga – Rainy Blue ~1997 Track~
Rainy BlueTokunaga Hideaki

A massive hit by Hideaki Tokunaga, known for many cover songs.

Its highly expressive lyrics are musically acclaimed, and it’s a quintessential Japanese breakup song covered by a wide range of artists.

It has long been a beloved and highly popular choice for karaoke.

MPRINCESS PRINCESS

[Tonight, Birth! Music Champ] “M” (PRINCESS PRINCESS) / Sumina Maruyama (Maruyama Sumina)
MPRINCESS PRINCESS

When it comes to Princess Princess’s heartbreak songs, “M” is the one that stands out.

It’s sung by a female vocalist, but it also has a different charm when sung by a man, which I recommend.

Though it’s a very sad song, its beautiful melody is captivating, and it’s the kind of piece you want to sing with heartfelt attention to every word of the lyrics.

Lonely Tropical FishWink

Lonely Tropical Fish (Music Video)
Lonely Tropical FishWink

Speaking of WINK, they were a female idol duo that took the world by storm from the 1980s to the 1990s.

They have several heartbreak songs, and “Lonely Tropical Fish” is one of them.

First of all, the title is brilliant.

For people in their 40s, it’s a very nostalgic track.

My loverGorin Mayumi

Based on its lyrics, it’s a heartbreak song that strongly brings to mind an autumn avenue of ginkgo trees.

The quintessential breakup-song lyrics are very direct, with raw poignancy throughout, and it’s well known as a track often sung by women at karaoke.

LOVERS AGAINEXILE

EXILE / Lovers Again (Short Ver.)
LOVERS AGAINEXILE

If you really want to plunge into the depths of despair, sing this song and let yourself soak in all your memories of her.

Once you hit rock bottom, the only way left to look is up, so you should be okay.

I hope good things come your way from here on out.

winter againGLAY

An adult heartbreak ballad.

For those who can’t forget someone even after breaking up, I hope this song lets you sink even deeper into those feelings—and helps you somehow make it through the cold winter.

It’s not exactly that kind of song, but it’s one you can immerse yourself in, reminiscing about those happy days, so please take your time and sing it.

Sly womanSha ran Q

Sharan Q “Sly Woman” OFFICIAL MUSIC VIDEO
Sly womanSha ran Q

This is a hardcore heartbreak song, so I want you to sing it while deliberately facing reality.

In the end, the song concludes with a lingering desire to see her again, so it’s a perfect recommendation for someone who still can’t get over his ex.

Sing it and give her a call.