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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] Summary of Nostalgic Popular and Classic Vocaloid Songs (71–80)

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 Enbizaka mothy

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?

Miracle PaintOSTER project

official MV Miracle Paint feat. Hatsune Miku - OSTER project
Miracle Paint OSTER project

This is a big band jazz-style Vocaloid song that’s sure to put a smile on your face with its bright vibe! Created by OSTER project, also known under the name Fluffy Cinnamon, it was released in November 2007.

The piece is filled with gratitude for a friend who drew the illustrations, and its happy mood shines through both the arrangement and the lyrics.

The walking bass and light, sprightly piano really get you grooving.

At the time, the technique of having Hatsune Miku scat was also an unusual approach to tuning.

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

Ievan Polkka

You might not recognize it from the title alone, but if you were following the Vocaloid scene back then, you’ll know it the moment you hear it—“Oh, this one!” It’s the song that had Hatsune Miku sing the Finnish folk tune “Ievan Polkka.” This cover video was what sparked the association of Hatsune Miku with leeks.

The chibi-style Miku that appears in the MV came to be known as “Hachune Miku,” and afterward she was turned into figures, manga—you saw her everywhere.

It really takes me back to those days when the Vocaloid scene was steadily expanding.

Hello, WorkerHayashi Kei

"Hello, Worker" – KEI feat. Megurine Luka
Hello, Worker Hayashi Kei

It’s a rock number that gives you the motivation to work and the energy to make it through the day.

Created by Vocaloid producer Hayashi Kei, also known as “Not-an-illustrator KEI,” it was released in 2011.

The standout feature of this song is, of course, that it takes “work” as its theme.

At the moment you’re about to enter society, you can’t help but worry, “What am I capable of? What do I want to do?” This piece offers comfort for those feelings.

Please take a moment to think back to who you were when you first listened to it.

Pumpkin SyndromePolyphonicBranch

[Kagamine Rin/Len] Pumpkin Syndrome [Original]
Pumpkin Syndrome PolyphonicBranch

PolyphonicBranch’s “Pumpkin Syndrome” is a unique song themed around Halloween.

Its delicate and diverse instrumentation colors the season and captivates listeners, while the light, upbeat groove and pleasantly shifting time signatures further enhance its entertainment value.

In particular, the call-and-response between Kagamine Rin and Kagamine Len grabs the listener’s attention, and the storylike lyrics create a fantastical atmosphere.

The tale woven by the costumed characters offers both fresh surprises and a sense of familiarity.

It’s a perfect track for a party with friends on Halloween night.

Hajimete no Otomalo

The more you listen, the richer it becomes—a moving ballad number.

Created by Vocaloid producer malo and released in 2007.

In unadorned words, it conveys Hatsune Miku’s feelings.

Its warm message—“I’ll sing for you anytime”—has gently wrapped the hearts of listeners.

If you listen now, you might even cry as you remember who you were back then.

The Hatsune Miku voice library was released in August 2007, and this song was published in October… truly a “masterpiece from the very earliest days of the Vocaloid scene.”