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[Memories] A Collection of Nostalgic and Classic Popular Vocaloid Songs

It’s no exaggeration to say that Vocaloid grew up alongside internet culture.

Sparked by the release of the MEIKO library in 2004, countless masterpieces have continued to be created up to the present day.

Especially after Hatsune Miku’s debut in 2007, there are surely people who devoted their entire youth to the explosive Vocaloid boom centered on Niconico Douga.

In this article, we’ve put together a collection of nostalgic Vocaloid songs that helped shape that scene.

It’s a playlist perfect for diving into memories or discovering something new!

[Memories] Collection of Nostalgic and Classic Popular Vocaloid Songs (81–90)

FREELY TOMORROWMitchie M

[Amazing Tuning] Hatsune Miku 'FREELY TOMORROW' [Official PV]
FREELY TOMORROWMitchie M

Posted in 2011, Mitchie M’s “FREELY TOMORROW” is a nostalgic Hatsune Miku song.

Its unique appeal lies in a distinctive sound that blends an 80s–90s dance-music vibe with a catchy yet slightly quirky and enigmatic vocal melody.

Also, the phrase “XX sugee” (meaning “XX is awesome”), which spread thanks to this song, was used in the titles of many videos at the time—so for those who witnessed it in real time, it’s likely to feel all the more nostalgic!

The Tailor of Enbi Hillmothy

[Official] The Tailor of Maruosaka / Megurine Luka [Japanese-style Story Original]
The Tailor of Enbi Hillmothy

This is a highly narrative-driven work that combines a Japanese-style sound with a mad, distorted worldview.

The song is by mothy, also known as Akuno-P, and was released in 2009.

It is one of the Seven Deadly Sins series alongside pieces like “Conchita, the Epicurean Daughter,” and was created with the theme of “envy.” The protagonist, a tailor, becomes jealous when he sees the person he loves walking with a woman who isn’t him… Written like this, it might seem like the theme is “infidelity.” But those who’ve listened know that’s not it, don’t you?

When the con man starts to laughNashimoto Ui

With jagged, distorted guitars, a roaming bass, brisk drums, and a noisy vocal, this rock track’s ensemble is irresistibly cool.

It’s a song by Nashimoto Ui, a Vocaloid producer known for band-driven sound, released in 2009.

Fans of grunge and alternative rock likely found it especially striking.

And that ending…

it gives you chills.

Back then, a fan-made animated MV based on the song was also widely watched.

Lili Lili Burning Nightsamfree

Let’s pump up the energy with a hype, upper-tempo Eurobeat vibe! Produced by Vocaloid producer samfree, “Riririri★Burning Night” was released in 2010.

It’s an electric tune that follows in the footsteps of “Luka Luka★Night Fever,” which came out in 2009.

As the title suggests, the track features the Lily voice library, and in 2014 it became the first original Lily song to surpass one million views, drawing lots of attention.

The cool tone of the vocals fits the style of the track perfectly.

Kokorotoraboruta P

This piece conjures a grand, expansive world by blending electric sounds with the tones of traditional Japanese instruments.

Created by the popular Vocaloid producer Toraboruta-P—also known for hits like “Toeto” and “Four-Leaf Clover”—it was released in 2008 and included on compilation albums such as EXIT TUNES PRESENTS Vocalostar feat.

Hatsune Miku.

The story-driven lyrics, centered on a robot with a heart, deliver an achingly poignant finish.

Some listeners may have found themselves in tears the very first time they heard it.

from Y to YJimii Samu P

A Vocaloid song that portrays a breakup with a lover, tightening your chest with emotion.

It’s a track by Vocaloid producer JimmyThumb-P, who also created hits like “Calc.” and “No Logic,” released in 2009.

A heart-stirring ballad that wraps a bittersweet piano rock sound in gentle strings.

While the lyrics carry the sadness of a “farewell song,” a sense of hope comes through in the end—perfect for when you want to move on from a broken heart.

[Memories] A Collection of Nostalgic and Classic Vocaloid Hits (91–100)

Cowardly Task Force UrotanderShin P

If you haven’t heard it before, first take a look at the number of comments on the video page.

I have a feeling you can get a sense of the atmosphere at the time it was released just from that figure.

It’s a song by Vocaloid producer Shin-P, released in 2007.

As the title suggests, it’s the theme song for ‘Hikyou Sentai Urotander,’ and the lyrics convey Urotander’s ‘anything goes as long as we win’ spirit.

That whole surreal vibe really feels like internet culture from back then.

If you listen to it with someone you’ve known for a long time, it might spark some nostalgic stories.