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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A selection of challenging songs that will earn you respect if you can nail them at karaoke! (1–10)
Medianochezutto mayonaka de ii no ni.
This song was released for streaming on January 29, 2026, and the music video was handled by TV♡CHANY, who also worked on “Hippocampal Growing Pains” and “Can I Meet You With Cream?”.
The term “Medianoche” generally refers to a Cuban hot sandwich and is said to mean “midnight.” Among fans, it’s even called “the hardest song in Zutomayo’s catalog,” and when you listen, it’s packed with so many elements that you probably won’t be able to memorize it in one go.
In any case, it’s a song where you have to pay attention to switching between chest voice and falsetto, the rapid-fire sections, sense of rhythm, and breathing timing.
Until you get used to it, I recommend listening at a slower playback speed.
Serenadenatori
This is a newly written song serving as the ending theme for the third season of the TV anime “Oshi no Ko.” It was released as a single on February 4, 2026, and is a dance number themed around vengeance and self-sacrificial love, inspired by the character Aqua.
The arrangement is by Tsumiki, resulting in an addictive sound.
Natori himself described it as a “cursed song,” saying he delved deeply into Aqua’s heart during production.
Because the A and B verses are sung in a matter-of-fact manner, the chorus feels suddenly higher, making it easier to belt.
If you keep your resonance from the very beginning—raising your eyebrows and placing the resonance toward the head—you’ll be able to transition smoothly into the chorus, so make sure to maintain your resonance position.
vivariumAdo
Released on February 18, 2026, this Vocalo-rock track, which she wrote and composed herself, is based on her autobiographical novel “Vivarium: Ado and Me,” out on the 26th of the same month, and it cries out the conflict between self-denial and the search for light.
The live band’s master, Takayoshi “CO-K” Kokei, handled the arrangement, and the first live-action jacket photo is also making waves.
Listening to the song, it feels quite complex.
The tempo is fast, with melodies coming one after another, making breath placement difficult; without being able to take instant breaths, I think it’s hard to sing the whole thing flawlessly.
On top of that, head voice and chest voice alternate repeatedly, so you end up using more breath than you’d expect.
Relax your body and focus on diaphragmatic breathing.
lulu.Mrs. GREEN APPLE
This is the first digital single announcing the start of Mrs.’s “Phase 3.” Written specifically as the opening theme for season 2 of the TV anime Frieren: Beyond Journey’s End, it’s a song themed around “reincarnation,” depicting the strength with which life and memories are passed on.
Although it’s sung with a generally gentle feel, the song itself sits quite high, so breath control and core stability are very important.
If your body wobbles, your voice will also waver instead of projecting straight.
In particular, this song gradually rises in range toward the latter half, so your endurance will be tested—keep your core firmly in mind.
Shifting your weight onto one leg lets you stand solidly on a single leg, preventing your center of gravity from swaying and making it easier to produce your voice.
In that position, it’s crucial to sing while using your breath properly.
UnderdogEVE
In a modern world where the truth has become hard to see, this is a quiet cheer song that says, “It’s okay to be like an underdog,” offering closeness to everyone living with hurt.
It features a highly addictive melody and a sharp, cutting-edge track, and the music video—following “lazy cat”—is a fully animated piece produced by OFF SCRIPT.
The tricky part of singing “Underdog” is the B-melody, where lyrics and melodic lines come in quick succession.
Also, the sections that gradually rise in pitch are spots where you can easily run out of breath.
If you sing without stopping, with the feeling of sprinting up a flight of stairs and building momentum, you should be able to get through it.
Once you clear this B-melody, switching smoothly between chest voice and falsetto in the chorus will likely come more naturally.
humanŌishi Masayoshi
For the TV anime Human-Hating Teacher of the Nonhuman Classroom, the opening theme’s lyrics, composition, and arrangement are all by Masayoshi Oishi.
A self-proclaimed lover of humanity, he says this is one of his favorite songs for how it captures the work’s worldview.
In the music video, he performs a dance in a school uniform, so learning the choreography and singing along is a lot of fun.
Oishi’s hallmarks are his clear, chest-voice delivery and high tones typical of anison singers.
NINGEN is quite fast-paced and keeps to high notes, so if you don’t sing crisply and confidently, you’ll fall behind the tempo or end up with a thin voice.
In particular, the last chorus modulates and raises the range.
Engage your core to keep your voice steady, and project firmly as if sending your voice far away!
TEST MEchanmina
This is the opening theme song for the third season of the TV anime “Oshi no Ko.” Centered on strong messages that sync with the series’ worldview—like “grudge” and “don’t test me”—it’s a fiery track that feels like a self-pep talk.
In the music video, visuals aligned with the lyrics unfold, from captivating performances to an intense midsection pas de deux, resulting in a piece packed with Chanmina’s allure and charisma.
Dynamic contrast is crucial; if you sing it too evenly, it could turn into a completely different song.
Especially in the chorus, exaggerating the accent on the first beat feels just right and lands stylishly.
The song itself is on the short side at 2 minutes and 51 seconds, so if you want to sing something intense, give it a try!