1990s Male Singer-Songwriters: Popular Song Rankings [2026]

Ruby RingTerao Akira31rank/position

Ruby No Yubiwa

Akira Terao, who thrived not only as an actor but also as an artist, had a mega-hit with “Ruby no Yubiwa,” a song that has continued to be sung at karaoke for many years.

To sing this song stylishly, it’s important to first understand your own vocal quality.

If you have a low voice, you can sing it with the same downbeat feel as the original.

If you have a higher voice, try raising the key on purpose.

It’s a song that still sounds cool even with a raspy delivery, so give it a try.

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Ryo

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Goodbye, Summer DaysYamashita Tatsuro32rank/position

Tatsuro Yamashita “Goodbye Summer Days”

Tatsuro Yamashita’s 21st single, released in May 1991, is a classic inspired by his own high school experience of being caught in a sudden shower at an amusement park pool and seeing a rainbow after the rain.

It beautifully captures the bittersweet feeling at summer’s end and the tender emotions of first love before adulthood.

The song was also used in a commercial for Dai-ichi Life and released as an advance single from the album “ARTISAN.” It reached No.

12 on the Oricon Weekly Chart and was certified Gold.

It’s a quintessential summer ballad recommended for those who want to relive their youthful memories or nostalgically revisit the delicate romances of those days.

A long nightMatsuyama Chiharu33rank/position

A long night

This song can be considered a quintessential example of cool Showa-era kayōkyoku sung by a male vocalist.

Known as a leading figure in folk music, Chiharu Matsuyama boldly transformed his style into a rock-oriented sound with this ambitious work, released in 1981.

Featuring passionate lyrics and a powerful arrangement, it vividly captures the emotions of a heart swayed by love.

It became Matsuyama’s biggest hit, selling a total of 866,000 copies.

While described as an “unconventional rock song,” it won over many fans.

Nail the soaring melody in the chorus, and it’s guaranteed to fire up any karaoke crowd!

Winter is starting.Makihara Noriyuki34rank/position

[Official] Noriyuki Makihara “Winter Begins” (Music Video) [4th Single] (1991) / Fuyu ga Hajimaru yo

This is a winter-song masterpiece released in November 1991 by Noriyuki Makihara, who had a huge breakthrough that year with “Donna Toki mo.” It was used as the commercial song for Sapporo Beer’s Fuyu Monogatari in the 1991 season, and I’m sure many people enjoy a beer while listening to it, just like the lyrics say.

Beyond the wonderful melody and vocals, and the perfectly crafted sound arrangement that begins with the harmonica in the intro, the lyrics—skillfully contrasting summer memories with the onset of winter—are simply outstanding.

It’s a shining example of the genius singer-songwriter Noriyuki Makihara at his best.

He has created many other winter songs as well, so be sure to check those out too!

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KOH-1

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Hold my soulHimuro Kyosuke35rank/position

Hold my soul

Kyosuke Himuro, who took the world by storm as the vocalist of BOØWY and enjoys immense popularity as a solo artist, released “Tamashii wo Daite Kure” in October 1995 as the first single following his move to a private label.

It’s a rock ballad perfect for listening to on long autumn nights.

Chosen as the theme song for the TV drama “Kaze no Keiji: Tokyo-hatsu!”, it reached No.

2 on the Oricon weekly chart.

Majestic strings and a heart-piercing melody blend beautifully with Himuro’s uniquely charismatic vocals.

It’s a track you’ll want to savor in the season when people yearn for connection.