Here's a list of the "classics" that I know of. These are songs that are beloved in the Vocaloid fandom as a whole, and are often referenced or have memes made about them. If I'm missing anything, please let me know! I'm still new to the vocaloid fandom considering its history and age.

Here I will highlight some of the more recent "trendy" Vocaloid songs that got really big during my time as a Vocaloid fan.

These 3 fall into the same time period in my mind, I was starting to get into vtubers and Hololive, and I remember EVERYONE had either a king cover or a vampire cover, or both... lol
I even found a poster of Polka's cover of Vampire, godly book-fair find. That's when I put DECO*27 on my radar.
as for Lagtrain, it didn't live off the covers like the other too, but it was such a vibe, man. I had a Lagtrain themed wallpaper for, like, the whole year.

After that, Kairiki bear dropped this banger which led me to explore their music further, and introduced me to flower. Till now I'm in love with the illustration style for the thumbnails/MVs

I was already a PinocchioP fan when this song dropped, but damn was it stuck in my ear ever since. PinocchioP's music has a unique PinocchioP flavor, yet every song is so different! Here are some of my personal favs With or Without Me (very underrated) and Anonymous M (very unique)

Another DECO*27 song that took the internet by storm. This song's popularity is owed in part to @x_cast_x's animation which got VERY popular on vertical video platforms, but I do also think the song stands on its own; it's very catchy.

It's not every day you get to see a miku song with a magical girl beam, along with the way that section was animated; it inspired many artists to make their own versions, turning this into a popular animation meme.

I cant in good conscience write about trending Vocaloid songs without mentioning Mesmerizer, so here.

More goofy Teto hehehehehehe...

Writing this made me realize how much a quality music video helps with a song's popularity. While "Monitoring" and "Mimukauwa Nice Try" both have their own merits, The music video just elevates them so much. "Mimukauwa Nice Try" in particular, has a lot of unique decisions and turns the situation itself into part of the song.

Tetoris was even more goofy Teto, using the tetris theme as a base makes it stick to an already catchy tune.

Finally, SAWTONE's "Confessions of a Rotten Girl" was just the perfect song to represent the Fujoshi community; they have basically adopted it as their national anthem now.

Songs and creators that need more love frfrfr, in no particular order:

I so hard wanted to talk about Jamie's music in all the above sections, but I couldn't find the right opportunity, so I'm making a section JUST to highlight her wonderful work.

I honestly think you should go and listen to all the songs; they are ALL worth a listen, AND the way she keeps coming back to old tracks with little references or soundbites is just so... *dies*

I can't just list out her entire library, so I will highlight some of my personal favorites from her.

I am pretty certain the first song I came across was "ROT FOR CLOUT" it was very different compared to the other Teto songs I had listened to so far, and so it stuck with me. You can hear the "Jamie lick" at about 1:10; it's a reoccurring motif in ALOT of Jamie's music, we will most definitely hear this again, but for some more examples, I Wish That I Could Fall at 3:30, Cadmium Colors at 2:22, and Radiant Revival at 2:04.

Then this goofy shrimp showed up one day, it's just the perfect mix of funny meme and catchy song. The way Jamie tunes their Miku makes her sound so cutely expressive! And the music video is just so much fun, it's just a bunch of friends messing around with a Miku plus :D

I'm going a bit out of order here, but I want to keep "Machine Love" for last. "BIRDBRAIN" is just Teto being literally me. The MV's animation + real life is one of my favorite aesthetics, I've tried making similar before, but I don't really have the art skill for it T_T. This song yet again just feels so fun, through the real life shots and the funny bit at 3:00+ you can really tell how much fun she's having with the MVs and music. You can also hear a light Jamie lick motif at 0:40

I could go on and on and on about this song, it's not just a tribute to "Song of the Eared Robot"; It is a tribute of love to Teto, as well as art and music in general. Adding onto all that, the idea of a machine falling in love is one I've been fascinated with for a long time, Monika is my favorite DDLC character after all :)

But going back to what I said about being a tribute to Teto, the MV is filled to the brim with references to other songs, Teto memes, and even previous Jamie Paige songs. The song and MV are also a mixed effort between a BUNCH of different artists, all adding their own unique experiences through their art... It is an amalgamation of pure and sincere human emotion, which is fascinating to think about in the context of this song being about a computer learning to feel...

Jamie lick at 2:05

Links:

• Jamie's personal website.
• Jamie's youtube.
• FLAVOR FOLEY a music circle Jamie is a part of, also pure peak.