[For Men] Masterpiece Enka Songs with High Difficulty
Needless to say, singing enka requires above-standard vocal ability and expressive power, and it also involves enka-specific techniques like kobushi (melodic ornamentation), so it’s anything but easy.
Even people who aren’t very interested in enka will likely think, “This person is a really good singer,” when they hear someone handle enka well at karaoke.
Here, we’ve researched and compiled masterpieces by male singers that are particularly tough to sing—high-difficulty enka songs.
Along with timeless classics, we also include recent hits.
If you’re confident in your singing, we’d love for you to try these at karaoke—so be sure to check them out.
By the way, we’ve also published another article featuring songs by female singers, so don’t miss that one either!
- [For Women] Masterpiece Enka Songs with a High Degree of Difficulty
- [2026] Amazing If You Can Sing It! Classic Enka Masterpieces [Male Singers Edition]
- [Enka] Songs That Are Easy to Sing Even for the Tone-Deaf [Male Singer Edition]
- A roundup of male enka singers who represent the Showa era
- [Male Singers Edition] The face of New Year’s Eve! Enka singers who appeared on the Kōhaku Uta Gassen
- Enka songs that are easy for men to sing: a roundup of tracks to try at karaoke
- [For Beginners] Recommended Enka Masterpieces for Karaoke — Male Singers Edition
- [Men] Enka Songs That Can Score High in Karaoke
- Men’s enka: a collection of classic songs portraying the way men live and their fighting spirit
- [For Beginners] Recommended Enka Classics for Karaoke — Women Singers Edition
- [Original Endoru] A Collection of Easy-to-Sing Songs by Junko Ishihara [2026]
- [2026] Enka Songs That Are Hard to Sing – Male Singers Edition
- [2026] Idol-Worthy! A Roundup of Handsome Male Enka Singers
[For Men] Masterpieces of Enka with High Difficulty (1–10)
Chikumagawa RiverItsuki Hiroshi
Hiroshi Itsuki, a singer Japan is proud of, has performed numerous beloved national hits.
Among his many classics, Chikumagawa, released in 1975, is one of his signature songs set in Nagano Prefecture.
Sung gracefully over a triple meter, its melody is challenging, spanning a wide range from the low notes of the verse to the high notes of the chorus.
Even Itsuki himself has described it as “not to be sung carelessly.” The key is to convey a rich sense of travel and scenery while taking care not to let the words become muddy in the lower register.
Tears and a solitary drinkAoyama Shin
Portraying in poignant detail the feelings of someone who has lost a lover, this work is likely to become one of Arata Aoyama’s signature songs.
Its profound sadness and sense of loneliness are powerfully conveyed, with lyrics that tighten the listener’s chest and a wistful melody that resonates deeply.
Aoyama’s clear, translucent voice beautifully enhances this heartrending worldview, and the emotionally rich singing in the chorus is especially striking.
Although it’s a highly challenging piece that demands enka-specific vocal techniques—such as vibrato and nuanced dynamics—it also allows the singer to fully express their emotions.
When attempting it at karaoke, it’s key to relax and sing while visualizing the scenes depicted in the lyrics.
ancient castleMitsubishi Michiya
When it comes to timeless, melancholy Japanese classics, this song is the first that comes to mind.
Its lyrical poetry and rich melody blend beautifully, stirring the listener’s heart.
Through the image of a decayed castle, it poignantly sings of lost glory and nostalgia for bygone days—truly the essence of enka.
Since its 1959 release, it has remained beloved by many and is a karaoke staple.
Yet its difficulty is well known: Mihashi’s distinctive vocal timbre and expressive power, along with the wide-ranging melody, put any singer to the test.
Even so, it’s a song I especially hope those with a wealth of life experience will try.
I long for Southern HokkaidoKoyama Yudai
A debut song by Yudai Koyama that sings of Hokkaido’s majestic nature and his love for family.
The lyrics vividly depict the scenery of Southern Hokkaido, and his powerful, folk-influenced vocals leave a strong impression.
Released in April 2024, this work fully expresses his love for his hometown and resonates deeply with listeners.
While honoring the tradition of enka, his performance at the young age of 21 feels fresh.
With its wide vocal range and nuanced kobushi ornamentation, the song is technically demanding, yet Koyama’s “magic voice” captures it beautifully.
Highly recommended for those who have left their hometowns or anyone who wants to savor the depth of enka.
Solo Journey with the Tsugaru ShamisenSaisei
Set against the harsh climate of Tsugaru, this song portrays the lonely feelings of a protagonist who leaves their hometown and continues their journey.
The powerful timbre of the Tsugaru shamisen blends beautifully with Ayasei’s emotionally rich vocals, resonating deeply with listeners.
Released in May 2020, the track drew attention as Ayasei’s second single.
The unique tone of the Tsugaru shamisen and Ayasei’s vocal prowess create a soundscape that will feel fresh not only to enka enthusiasts but also to listeners across generations.
While the song is relatively challenging to sing, imagining the landscapes of Tsugaru while performing will surely make it a piece that touches the heart.