I'm listing 10, but I can't really rank them, so that's why they're not called my Top 10 Vocaloid songs. I'll try to go in the order I found the songs. This will also include covers by real people or other Vocaloids/Utauloids. Be prepared for a lot of Kyaami/Cilia. Also, quite a few of these songs contain s*i**dal implications or some occasional a**se implications. I'll point out songs that are sensitive.
Odds and Ends was the first Vocaloid song that I got genuinely invested in, back in middle school when my best friend at the time was super into it. The visuals paired with the lyrics made me cry. And, if you've known me for a certain amount of time, you'll know that I love when media makes me cry. So this song really opened up my mind to the potential of Vocaloid.
This one is a bit sensitive. Rolling Girl (particularly the Mawarine Shuu version by Kyaami). I first got into the Wowaka/Miku version during my Undertale phase, on a Papyrus animatic. Interestingly enough, a different Papyrus animatic introduced me to Kyaami and her covers (Baloney Speaker), and I quickly found this cover. Normally, the version of a song that I prefer is the first version I hear. But Kyaami is such a tuning goddess that this version has a CRAP ton of vocal power and emotion.
This one is very sensitive. My R, particularly the Rachie version. I like songs that have a disconnect between the melody and the lyrics. So having a very upbeat, playful melody interact with the blunt, matter-of-fact discussion of death is something that really appeals to me. And the desperation in Rachie's voice when the modulation happens... WOW!
The Meltberry cover! This song is hella catchy and super fun to sing! The video is very stylish and the discord within the song grew on me a LOT. I have good memories with this one. Listening to it on repeat on a long car ride and jamming out to it all weekend... I don't have TOO much to say about it, but I definitely love it.
Electric Angel! I like the Kagamine twins cover much more than the Miku version just cause I prefer the energy and chiptune vibes. This song, like the one above it, is hella fun to sing and really catchy. This sort of sparked a Vocaloid "reawakening" in me, causing me to try and find all sorts of new songs. Also, I got weirdly philosophical surrounding this one... beings singing about their own status as something without wills of their own being given songs to sing... and the song they were given to sing was about said status... so they never really had free will in the first place... MOVING ON.
More of Kyaami being a Tuning Goddess with the Kagamine Len version of Lost One's Weeping. I love how angry and frantic this one sounds. I legit wrote a college essay about a very similar topic the same day I found this song. It was abt a misconception people have about my generation. This is one of a few Vocaloid songs that I crank up to nearly max volume, because it's one of the ones that feel way better if it sounds like it's being screamed to you.
Hachi/Yumi's Donut Hole... gosh, this one has inspired me creatively SO much. I first listened to it nonstop whilst I was reading one of my all-time favorite fanfics, "Project Rewrite." It was also what triggered me to create "Before I'd Met You All." All of the different layers and parts to this song make it really interesting to listen to, and the lyrics are very intriguing. It feels like you can make a lot of different stories out of them.
Ah, Parade of Mediocre People. The song I wish I had in middle school. I was a stereotypical r/notliketheothergirls and I was the worst. I like the different ways you can interpret what's going on, I like the fact that there are conversations going on that aren't necessarily being sung, I like that it's one of the only songs in the Diary of Underage Observation album with a happy ending, I LOVE the visuals. The beat is great. Overall? Real good.
Very sensitive. Mafumafu's cover of his own (originally Vocaloid) song, "Hated by Life Itself." I found this on a V3 animatic (don't watch it unless you've finished the game or got mercilessly spoiled). I cried. And then s*** started to hit close to home during a low point in my life, and I cried MORE. It's another one of those songs that I play at almost max volume. I want the desperate singing to melt my brain. Because it sounds SO emotional. The lyrics are top-notch and the singing is actually unreal.
Kyaami/Cilia once again, this time with her own song. This one is the most recent obsession. It's just so bright and cheerful and kind. The lyrics are full of cutesy images and sweet lyrics, and the beat is so infectious. It's not nearly as emotionally impactful as some of my other favorites, but it just makes me feel warm and fuzzy. Sometimes happiness is okay.
And that concludes my list of my ten favorite Vocaloid songs! I hope you all enjoy the music!!!