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Beautiful tear-jerking songs / songs that make you cry your eyes out

Tear-jerking songs recommended for men in their 20s: classic and popular Japanese tracks

When it comes to songs that make you cry, there are many that rely on sweeping, grand music to stir your emotions, but there are also plenty of works that move you from a more literary perspective.

Pay close attention to every word and phrase—the unique points of view and the precise choice of words that express feelings so accurately are truly striking!

Tearjerker songs recommended for men in their 20s: Classic and popular Japanese tracks (91–100)

Rainy BlueTokunaga Hideaki

It’s one of Hideaki Tokunaga’s signature songs, and its popularity is evident from how many artists have covered it.

He’s also re-recorded it himself, and the existence of several different versions is part of its appeal.

The lyrics vividly convey emotions like heartache and pain—chasing after a love that should have ended, or memories suddenly resurfacing—and the gentle, tender sound that seems to amplify those feelings makes the song resonate deeply in the heart.

FORK IN THE ROADTAKUI

FORK IN THE ROAD by Takui Nakajima
FORK IN THE ROADTAKUI

Takui Nakajima is beloved for his overwhelming vocal prowess.

This ballad, released in the ’90s, lets you fully savor his soaring, emotionally rich vocals.

There aren’t many voices that can move people this deeply, are there? Its grand melody and lyrics about parting will bring you to tears.

I wonder what kind of face that girl would make if I sank a long shot.Okamura Yasuyuki

Yasuyuki Okamura: I wonder what kind of face that girl would make if I scored a long shot.
I wonder what kind of face that girl would make if I sank a long shot.Okamura Yasuyuki

This is a youthful love song by the prodigy Yasuyuki Okamura, released in 1990 as his 13th single.

The very long title is striking, and the song imagines how, if only things were different, he could look cooler in front of that girl.

When you think about what lies behind the lyrics, it evokes a strangely poignant feeling—it’s a song that can move you to tears.

Bridge of Gloryyuzu

Eikou no Kakehashi – Yuzu (Full)
Bridge of Gloryyuzu

It’s one of Yuzu’s signature songs and is well-known by many people.

When your heart feels like it’s about to break, when you’ve suffered a setback, or when there’s a wall you want to overcome, this wonderful song lifts you up.

The chorus lyrics and melody are incredibly moving—it’s impossible to listen without tears!

Together foreverKobukuro

Kobukuro - Together for Eternity
Together foreverKobukuro

This is a highly recommended, moving song for weddings.

Both the lyrics and the melody really tug at the heart, and the harmony woven by the two voices is truly beautiful.

It’s a popular tear-jerking ballad, so be sure to listen to it while thinking of someone special.