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 (1–10)

windKobukuro

This is a ballad that sets bittersweet memories recalled with the arrival of spring to a gentle melody.

Released in February 2002 as Kobukuro’s fourth major-label single, it was used as the theme song for Fuji TV’s “Ucchi Kuru!?” and also inspired the drama “A Story I’ll Never Forget.” The lyrics trace feelings for a former lover and delicate emotions, as if time gradually melts away the pain.

Its depictions of spring are superb, and it’s a masterpiece that conveys not only sadness but also the strength to look forward.

The song was performed at the 57th NHK Kohaku Uta Gassen in 2006 and has remained beloved for years.

I’d especially recommend it to men who’ve had those moments when a past love suddenly comes back to mind and their chest tightens.

I wanted to kiss you again.B’z

This is a classic B’z ballad that portrays a heartrending love story between a man and a woman, set against the changing seasons from a summer meeting to a winter parting.

The lingering melancholy and Takahiro Matsumoto’s weeping guitar further deepen the sense of lingering regret and attachment.

Included on the album “IN THE LIFE,” released in November 1991, the song was initially a candidate to be released as a single, but was ultimately passed over because “ALONE,” which had a tie-in, was prioritized.

Even so, it remains extremely popular among fans, ranking 4th in the vote that determined the tracks for the best-of album “B’z The Best ‘Treasure’.” It’s the perfect song to sit with on a night when a fleeting moment brings back memories of a past love and tightens your chest.

I miss youBEGIN

It’s an extremely famous ballad as the debut single by BEGIN, a band from Ishigaki Island in Okinawa.

Carried by a melody tinged with the scent of the blues, Higa Eisō’s tender yet aching vocals resonate deeply.

The lyrics portray, with painfully real detail, the lingering feelings and overflowing regrets for a lost lover.

Even knowing there’s no going back, he can’t help but search for her traces—this broken-hearted song captures a man’s longing that truly hits home.

Released as a single in March 1990, it was also used in a Nissan commercial and as the theme song for the TV drama “Shin Konjiki Yasha: Hyakunen no Koi.” Celebrated on the show “Ika-ten,” this classic is a perfect pick for a quiet night, sipping a drink alone while reminiscing about past love.

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

You are freeCHAGE and ASKA

[MV] You are free / CHAGE and ASKA
You are freeCHAGE and ASKA

Recut from the 16th album “RED HILL,” this is CHAGE and ASKA’s 33rd single, released in November 1993.

At the time, it was featured as the commercial song for Asahi Soft Drinks’ “J.O.,” and the music video starring Hong Kong star Michelle Reis left a strong impression.

Blending urban sounds with 90s R&B and emotive choral work by 14 Karat Soul, the track is truly moving.

The lyrics, which accept a breakup by acknowledging the other person’s righteousness—a quietly adult kind of sorrow—are sure to resonate.

Because it unfolds at a relaxed tempo, you’ll want to be careful not to lag behind the rhythm, but it’s a song to sink into on a night when you want to gently soothe the pain of heartbreak.

I want to take only you away just like this.DEEN

Released in March 1993 as DEEN’s debut single, this masterpiece has long been cherished as one of their signature songs.

Its poignant melody and lyrics that portray a deep longing for someone drifting away strike right at the heart.

Written by Sho Uesugi and composed by Tetsuro Oda, it was also used in an NTT DoCoMo “Pocket Bell” commercial and went on to become a million seller at the time.

The sweet, clear vocals gently cradle the pain of heartbreak, making it a song many find themselves wanting to listen to in quiet moments.

It’s also a karaoke staple, a classic ballad perfect for singing with poise while reminiscing about those days.

It’s included on the album “DEEN,” so be sure to enjoy it with a sense of nostalgia!

Last SongGACKT

GACKT「Last Song」MUSIC VIDEO
Last SongGACKT

Starting from a silence like freshly fallen snow and gradually building into passion, this dramatic progression makes it one of GACKT’s most memorable ballads.

The poignant theme of a “last song” dedicated to a loved one resonates deeply with listeners.

Released as a single in November 2003, it also plays a crucial role in the narrative of the album Crescent and continues to be cherished by fans today.

It was performed at the 54th NHK Kōhaku Uta Gassen, a widely known episode where its overwhelming expressiveness deeply moved audiences at home.

It’s a song that gently stays by your side when you want to quietly accept a love that has ended, or on nights when you look back on the past alone and try to face forward.

My LifeMr.Children

Mr.Children, the powerhouse band that has produced countless classics and continues to lead Japan’s music scene.

This track, which closes their third album “Versus” released in 1993, is a hidden gem that was later included on the best-of album “Mr.Children 1992–1995.” Despite not being a single, it has long been cherished by fans and was even performed during their 2007 stadium tour.

The lyrics, which embrace the frustrations of everyday life and the pain of heartbreak as part of one’s own journey, really hit home.

Though it never had a flashy tie-in, Sakurai’s words—portraying down-to-earth struggles—may resonate especially with grown men who’ve tasted both the sweet and the bitter.

It’s a warm, encouraging number that helps you relax your shoulders when you’re feeling down.