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

Isn’t it in the 1990s that singer-songwriters began covering a wider range of musical genres and self-composed songs seemed to become the mainstream?

From among the many timeless masterpieces born in the ’90s, we’re highlighting popular tracks—focusing especially on those by male singer-songwriters—and presenting them in a ranking.

1990s Male Singer-Songwriters: Popular Songs Ranking [2026] (21–30)

An uncool way of getting dumpedŌe Senri29rank/position

Uncool Way of Getting Dumped (Senri Oe) / Takahashi Kosuke @ Aoyama RizM (2018/6/14) @takahashi_kosuke
An uncool way of getting dumpedŌe Senri

This is a signature song by Senri Oe, who enjoyed immense popularity as a singer-songwriter in the 1980s and 1990s.

It was also the theme song for the drama “Men Who Want to Get Married,” and it became a hot topic because Oe himself, who was active as an actor in the show, appeared in it as well.

His character is bright, funny, a bit uncool yet kind of cool—and the lyrics, which seem to reflect that persona, resonated with listeners.

Boys who heard this song surely shed tears, overlaying it with their own heartbreak.

Happy endingOhtaki Eiichi30rank/position

This is a gem of a love song that Eiichi Ohtaki released for the first time in 12 years as the theme for Fuji TV’s Monday 9 p.m.

drama slot.

Its gentle, heartwarming melody and lyrics that carefully weave together the feelings of a woman in love harmonize beautifully, propelling the song to a massive hit with 970,000 copies sold since its release in November 1997.

Used in the drama “Love Generation,” the track also became Ohtaki’s first solo entry into the Top 10, showcasing his rich musicality to the fullest.

Portraying a sweet and bittersweet love story, this song is recommended for those harboring feelings for someone special or wishing for a happy future with a loved one.

Male Singer-Songwriters of the ’90s: Popular Songs Ranking [2026] (31–40)

Ruby RingTerao Akira31rank/position

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.

A long nightMatsuyama Chiharu32rank/position

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 Noriyuki33rank/position

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

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!

Hold my soulHimuro Kyosuke34rank/position

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.

I love youKawamura Ryuuichi35rank/position

Ryuichi Kawamura “I love you” MUSIC VIDEO
I love youKawamura Ryuuichi

A heart-stirring ballad woven from a delicate singing voice and profound expressions of love.

Ryuichi Kawamura’s solo debut is a memorable masterpiece whose romantic melody is complemented by imagery evocative of waves breaking on the shore.

Chosen as the ending theme for the music program COUNT DOWN TV, the song was released in February 1997 and reached No.

4 on the Oricon Weekly Singles Chart.

It continues to shine with undimmed brilliance as one of Kawamura’s signature tracks.

This gem of a love song—delivered with his distinctive expressiveness and soaring high notes—will resonate deeply on a nighttime drive when love is in the air or during special moments with someone important.