Huge post is huuuuge. I picked a bunch of my favorite Halloween-themed/scary songs, but since almost all of them have different versions/videos, I ended up with nearly 30 videos under the cut, oops. I also included Youtube mirrors with subs for everything I could, because the lyrics are a great part of what makes these songs so awesome. Also please let me know if there are any broken links or whatever because hahaha SO MANY LINKS. ;;d
ENJOY, CHILDREN, AND HAPPY HALLOWEEN \o/
TRICK AND TREAT
【鏡音リンレン】trick and treat【オリジナル曲】Opening with an OSTER Project classic! Rin and Len go trick and treating and... a bit of cannibalism ensues. :3 A fun song with an awesome video that really manages to be creepy at times.
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Mirror with subs @ Youtube TRICK AND TREAT [KUROANE]
【 trick and treat 】 歌ってみたらものすごい楽しかった。ver.黒姉More of the same, but covered by Kuroane. Both her Rin and her Len voices are fantastic and she does a great job of bringing out the creepiness in the song.
CONCHITA, THE EPICUREAN DAUGHTER OF EVIL
【MEIKO】悪食娘コンチータ【鏡音リン・レン】Another classic, brought to you by Mothy aka Aku No P (that dude responsible for the "Of Evil" series) and in my opinion one of his best works. Meiko, Rin and Len sing about a woman who liked to eat everything. ♥
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Mirror with subs @ Youtube CONCHITA, THE EPICUREAN DAUGHTER OF EVIL [ARRANGE COVER]
【巡音ルカ】悪食娘コンチータ【アレンジカバー】A sort of classical-dance-y cover by Luka. I prefer the original by a lot, but this is a good alternative for people who may not be as fond of Meiko's voice (also, the PV is hilarious).
HOLD, RELEASE, RAKSHASA AND CARCASSES
【オリジナル曲PV】結ンデ開イテ羅刹ト骸【初音ミク】I pimped this before in my Hachi post and everyone and their mom knows it, BUT IT'S STILL HOGGING A SPOT IN THE RANKING AND IT'S AN AMAZING SONG and so you have to put up with my bias. :| Traditional Japanese song meets traditional Japanese mythology meets Miku and Hachi's talent. A must see for everyone.
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Mirror with subs @ Youtube CRAZY CLOWN
【KAITO・初音ミク】クレイヂィ・クラウン【オリジナル】Metaphors (?!) with really dark overtones, a happy circus-y music, and Kaito and Miku dressed up as clowns. It's really a shame the song is so short.
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Mirror with subs @ Youtube ALICE HUMAN SACRIFICE
【オリジナル曲】絵本『人柱アリス』【歪童話】The story of a little dream that didn't want to die and so it decided to trap people so that it could live forever. This is the original version of that one Alice Vocaloid song everyone and their mom knows.
ALICE HUMAN SACRIFICE [5 PEOPLE]
【ヤマイ トゥライ Re:A 歌和サクラ うさ】人柱アリスを5人で歌ってみたFeaturing Yamai, Tolie, Re:A, Utawa Sakura & Usa, this is in my humble (and perhaps biased) opinion the best Utattemita cover there is of this song. This version also comes with that one wicked awesome PV. IF YOU'RE GOING TO CLICK ON JUST ONE OF THE TWO, CLICK ON THIS ONE.
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Mirror with subs @ Youtube FEAR GARDEN
【鏡音リン】恐怖ガーデン【オリジナル】In which Rin has very questionable hobbies. The song isn't really all that great, but it gets over 9000 scary-guro points.
FEAR GARDEN [PV]
【グロ注意】 恐怖ガーデン 【PV】More of the same, but this time with a cute/horrible accompanying PV. Again, if you're going to click on just one, pick this.
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Mirror with subs @ Youtube SADISTIC VAMPIRE
【鏡音レン】「SADISTIC VAMPIRE」【オリジナル曲】Not scary at all, not even sadistic (the title has always been rather confusing for everyone, trust me), but this gets to be here just because vampires go together with Halloween and Len is a lot more dazzling than Edward Cullen. Not to mention it's a huge earworm that will not leave you alone for days.
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Mirror with subs @ Youtube SADISTIC VAMPIRE [USA]
(。・x・)つ 【SADISTIC VAMPIRE】を歌ってみた@うさUsa's cover! Which... doesn't exactly sound like Len, but is still pretty sexy and one of my favorite covers by her.
THE HUMAN WHO LOVES OGRES
鬼を愛する人(オリジナル曲)/Vocaloid-MEIKOThis is here just because I love Meiko and the song is great and the PV is even more awesome and more importantly, because I can. :)
DARK WOODS CIRCUS
【初音ミク・鏡音リン・レン】暗い森のサーカス【不気味ワルツ】Miku, Rin, Len, and a bit of Kaito sing about the scariest, saddest circus. Also welcome to Machigerita who will be showing up a lot in the rest of this post, because he is an absolute monster when it comes to Vocaloid horror.
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PV with subs @ Youtube DARK WOODS CIRCUS [3D FUNDOSHI]
3次元フンドシが「暗い森のサーカス」を歌ってみました。I can't decide how I feel about this fandom. It's really good, but half of the time, I'm listening to it and I forget there are no singing robots singing because all of the high notes are sung almost perfectly. This one comes with bonus voice acting and that yet another scary/gorgeous PV.
WIDE KNOWLEDGE OF THE LATE, MADNESS
【初音ミク】博識であるが故、狂気【ホラーソング】Machige strikes back with the prequel to Dark Woods Circus. I just put it afterwards because I've always felt it has a lot more impact this way. NO PLOTTY SPOILERS FOR YOU.
WIDE KNOWLEDGE OF THE LATE, MADNESS [PV + OMAKE]
【初音ミク】博識であるが故、狂気【PV+おまけ】This is the one you should click on if you absolutely refuse to give Machige more views. A PV that will make you go "AUGH WHY IS THIS SO CUTE AND YET SO TERRIFYING WHY WHY WHYYYY" over and over again. The omake at the end makes it extra awesome.
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Mirror with subs @ Youtube ARK
【鏡音リン・レン】 Ark 【再調教版】This one is here just for
nekokoban. ♥ A Rin/Len cover of the Sound Horizon song. (Also gratuitous pimping of the
Vocaloid_Horizon tag on Moontube, because ffffffff).
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Mirror with subs @ Youtube NECROCARNIVAL
【初音ミクオリジナル】necrocarnivalMiku, electronic, and a song that seems perfectly innocent until you look at the video illustration and the lyrics. Thriller meets Vocaloid, I guess.
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Mirror with subs @ Youtube CIRCLE ME, CIRCLE YOU
【童謡ホラー】 かこめかこめ 【巡音ルカ、初音ミク】A Miku-Luka duet about abandoned children who just want to play with you. How cute! :3 This one gets extra creepy points because it uses the traditional Japanese children's song. NIGHTMARES FOREVER.
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Mirror with subs @ Youtube BLACK AND WHITE WARD
【リンレンオリジナル曲】白黒病棟【疾走悪夢】Rin and Len, a hospital, and gore. This song is amazingly vague, and it's really hard to understand what's going without an accompanying video. The problem is, there's like fifty different PVs out there and they all sort of tell different stories, so here: have the
song tag and have fun looking at them all. :Dd
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A different PV with subs @ Youtube BLACK AND WHITE WARD [VALSHE]
【鏡音レン・リン】白黒病棟歌ってみたver.バルシェ【精神×統一】Valshe's cover with one of the prettiest PV's for this song out there. As always, her singing is gorgeous, even amidst a frantic, psychotic song.
ROTTEN GIRL GROTESQUE ROMANCE (STALKER)
【ミクオリジナル】ロッテンガールグロテスクロマンス【ストーカー】YANDELOID WARNING! But you could probably guess that from the title alone, right? :'D Another terrifying song by Machige, it doesn't even need a PV because the illustration alone is guaranteed to make you cry.
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Mirror with subs @ Youtube HALLOWEEN MONSTER PARTY NIGHT
【VOCALOIDオリ曲】ハロウィンモンスタァパーティナイトAnd now, for something slightly more cheery! ... Or is it? Meiko, Kaito, Miku, Lin, and Ren and Machigerita again. :'D
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Mirror with subs @ Youtube MRS. PUMPKIN'S COMICAL DREAM
【オリジナル曲PV】Mrs.Pumpkinの滑稽な夢【初音ミク】Last, but definitely not least, we have one Hachi's newest songs that came out a couple of weeks ago just in time for Halloween. There is no kinetic typography in this one, but that's okay because the PV is gorgeous anyway.
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Mirror with subs @ Youtube MRS. PUMPKIN'S COMICAL DREAM [MII-CHAN]
Mrs.Pumpkinの滑稽な夢を歌ってみたったver.みーちゃんAs opposed to all of his previous songs, Hachi actually released a karaoke track for Mrs. Pumpkin, which means everyone and their mom has covered it and... all of the covers I've found are equally great. But if I had to pick one, I'd go with Mii-chan's because he gives the song a completely different feeling and it's just... well, listen to it. A+++ awesome.