Pick out the challenging songs that will earn you respect if you can nail them at karaoke!
Have you ever thought, “I’d look so cool if I could get through this song at karaoke,” only to crash and burn halfway through?Songs that are hard to sing hide plenty of tough spots—wide vocal ranges, complex rhythms, and blisteringly fast phrases that barely leave room to breathe.But that’s exactly why the sense of accomplishment when you nail them is second to none.In this article, we introduce a wide variety of challenging songs that are worth taking on at karaoke.If you want to test your limits or are looking for a spark to help you level up your singing, let this guide you to your next song choice!
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- [For Men] Masterpiece Enka Songs with High Difficulty
- [Challenge] A compilation of Vocaloid songs that are difficult to sing
- [For Women] Masterpiece Enka Songs with a High Degree of Difficulty
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- Feel-Good Songs: Belt Them Out at Karaoke! A Roundup of Popular Numbers
- Recommended karaoke songs for male vocalists with high voices
Picked out tough songs that will make people take notice if you can nail them at karaoke! (301–310)
Outlineimase

Imase, known for his wide musical range from funky tracks to classic J-pop, has released a string of hits, and his new song is Outline.
This piece features a somewhat grand melody, and Imase’s signature falsetto appears in various sections.
In particular, the falsetto in this track is soft yet demands strong breath support and volume, making it recommended for those who want to focus on honing their technique.
Don’t worry about sticking to the original key—challenge yourself solidly within your own vocal range.
come againm-flo

The English part in the intro might feel like a challenge at first, but let’s have fun and gradually speed it up.
It felt similar to American pop songs, and for the parts where the words get densely packed, listen repeatedly and try to imitate them.
The rap section in the middle is also a good challenge.
Dawn and Firefliesn-buna

This is a song by the Vocaloid producer n-buna.
Since the original uses a Vocaloid, the gap between the low and high ranges is large, making it challenging to move smoothly through the scales.
A good tip for singing it well is to focus on projecting your voice from your diaphragm.
Make sure to articulate the words at the beginning of each measure clearly.
A Naked Heartaimyon

Aimyong’s 10th single, released in June 2020.
Aimyong’s mid-to-low register is incredibly appealing, and that charm is fully showcased in this song as well.
Because her natural tone is somewhat rich and full, I feel her high notes don’t often get the spotlight, but she can belt powerfully in chest voice even in the upper range, while skillfully switching to falsetto for expressive nuance.
To sing this, mastering smooth transitions between vocal techniques is essential.
I think it’s a very difficult song.
That said, the melody itself is very straightforward and easy to remember.
YELLikimonogakari

This is Ikimono-gakari’s 15th single, released on September 23, 2009.
It was produced as the set piece for the junior high school division of the NHK National School Music Competition.
Musically, it’s a very gentle, tender ballad with a very simple arrangement, so to deliver a convincing performance, you’ll need solid vocal ability and expressive singing.
Melodically, there don’t seem to be many highly difficult parts, so it’s a song where thoroughly understanding the piece—including the lyrics—and conveying that meaning is extremely important.
The highest notes aren’t that high either, but be sure to sing them with a firm, powerful high tone!
The wind is blowing.ikimonogakari

It was released in 2012 as Ikimono-gakari’s 24th single.
Chosen as the theme song for NHK’s broadcasts of the London Olympic and Paralympic Games, it reached No.
3 on the Oricon Weekly Singles Chart.
At the time of its release, it was the longest song in Ikimono-gakari’s catalog, and its high key makes it challenging to sing, but it’s a grand piece brimming with bright hope for the future.
Unfit to be a loverMiyuhan

This song, sung by Miyuhan, a multi-talented singer-songwriter from Kagawa Prefecture, is actually an answer song to Koresawa’s smash hit “Tabako”! This much-talked-about track is notable for its leap from a rather low, straining A verse to a chorus filled with sustained high notes, giving it a very wide vocal range.
Subtly delivering that range with a whispery, transparent tone seems more difficult than it might appear.


