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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!

Tear-jerking songs recommended for men in their 20s: Classic and popular Japanese tracks (81–90)

Becoming a Thousand WindsAkiyama Masashi

Masafumi Akikawa is a Japanese tenor who shot to fame with the song “Sen no Kaze ni Natte” (A Thousand Winds).

The song is based on the American poem “Do not stand at my grave and weep,” sung from the perspective of the deceased, and its lyrics are meant to encourage those left behind.

The opening line, “Do not stand at my grave and cry,” is particularly striking and seems to carry profound meaning.

What you gave meHOME MADE kazoku

HOME MADE Kazoku 'The Things You Gave Me'
What you gave meHOME MADE kazoku

I think this is the kind of song that really hits you in the chest when you listen to it some time after saying goodbye to someone important.

Even if you’re no longer together, you may find yourself remembering your gratitude and the memories you shared, with tears running down your cheeks.

Until the day I can no longer see youMs. OOJA

Ms.OOJA "Until the day I can no longer see you" (Short ver.)
Until the day I can no longer see youMs. OOJA

It starts with the piano, followed by a female vocal, and the band sound along with strings really elevates the chorus.

It also gives you the sense that the second verse will be enjoyable.

Why not take this opportunity to try it at karaoke? I’m sure you’ll have a great time.

The Last RainYasushi Nakanishi

An ultimate, heart-stirring ballad that vividly portrays a farewell in a rain-soaked city.

Yasushi Nakanishi’s clear, gentle vocals beautifully express the pain of heartbreak and lingering attachment.

This song dramatically captures complex emotions like the fear of losing someone you love and possessiveness.

Released in August 1992, it was used as the theme song for Nippon TV’s “Hitachi Ashita P-KAN Kibun!” Its popularity steadily grew, ultimately becoming a major hit with total sales of about 900,000 copies by 1998.

It has been covered by numerous artists, including Kumi Koda and EXILE ATSUSHI.

For anyone who has experienced heartbreak, it’s a timeless ballad that resonates deeply and begs to be sung along to at least once.

Your SongYasuda Rei

Rei Yasuda 'Kimi no Uta' Video Clip – TV Anime 'Natsume's Book of Friends Roku' Ending Theme
Your SongYasuda Rei

It starts off with a drama-like atmosphere, then the quiet first verse comes in.

It flows into the pre-chorus and smoothly reaches the chorus.

It’s sung by a female vocalist, but the lyrics resonate with men as well, and even when you’re tired, it gives you a little boost.

It’s the kind of song you want to listen to when you’re in that mood, time and again.

Love DrizzleShonan no Kaze

Shonan no Kaze “Koi Shigure” MUSIC VIDEO
Love DrizzleShonan no Kaze

This is a song I’d like to recommend to anyone who has had to say goodbye to someone they loved very much.

If you’re trying to find a new love but can’t seem to move forward, I think this song is perfect for you.

Listening to it and having a good cry might help you feel refreshed.

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.