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- The Decepticons (or Destrons) get a pretty badass one in Transformers: The Headmasters, sung by Mr Hironobu Kageyama, no less.
- Plenty in Mermaid Melody Pichi Pichi Pitch. The first season only had two. "Kuro no Kyousokyoku ~concerto~" was a dark rock revelry filled with Minion Shipping and singing about breaking the bonds between the mermaids; appropriately enough, it's introduced around the same time as Caren, who threatens to tear the group apart, and it's eventually defeated by a song called "Kizuna" (Bonds). "Return to the Sea" hinted at Sara's motivations and got a Triumphant Reprise near the end. The second season gave the Black Beauty Sisters another song, "Yami no Baroque", much like their previous song, and gave each of the new villains their own songs where they sing about their powers (Lady Bat about hypnotism and vampirism, Lanhua about her instant minions, Alala about her Lotus Eater Machine stars) or their loneliness (Michel's "Tsubasa wo Daite", which also hinted at his connection with Michal because her "Ashita wa Mienakute" used some of the same music).
- Holy--look at the Lyrical Dissonance in "Yami no Baroque". An upbeat, pop karaoke tune about crushing, nihilistic despair.
- Though she doesn't sing it in the context of the series, one of Ryouko Asakura's image songs is a rock/techno villain song about the inferiority of humans and their emotions, her inability to feel kindness and joy and her being left out of the end credits.
- She also sings a slightly modified version of "Hare Hare Yukai" in which she sings that even if she knew everything she'd never be able to change her fate. And of course, if you don't speak Japanese, this sounds exactly like the optimistic original version.
- In a similar vein, the first season of the Digimon anime features numerous songs for the villains, most notably first Big Bad Devimon's "Dark Wing" and the Not-So-Harmless Villain second Big Bad Etemon's "Love Serenade." Note that these were also the name of their main attacks.
- Ken Ichijouji, Beelzebumon, and Duskmon had villain songs too.
- Beelzebumon's is weird because he seems to be singing as Blast Mode (he talks about having wings), but he's not a villain anymore by the time he reaches that form.
- Digimon Xros Wars gives us "Dark Knight - Immortal Lord", a song where DarkKnightmon boasts about how he's the only real badass in town and that he's gonna show the good guys how far beneath him they are.
- Ken Ichijouji, Beelzebumon, and Duskmon had villain songs too.
- Team Rocket from Pokémon had their own self-sung theme, at least on one of the American soundtrack albums: "Double Trouble". Though, like some examples above, this also falls into the Quirky Miniboss Squad territory (though "The Boss" does chip in a few lines, too).
- They get their own song in the Japanese version, too. Two of them, in fact: the bombastic "Rokketo-Dan yo Eien Ni" (Team Rocket Forever) and the more comical and fast-paced "Maemuki, Roketto-dan!" (Look Ahead, Team Rocket!)
- They also get a song in the show itself when they decide one day that they're tired of doing their motto over and over again. Ironically, the song is only ever heard again once, and then only in part.
- One of the Japanese soundtracks had the song "Ware wa Collector / I am a collector" for Lawrence III AKA the collector from Pokémon 2000.
- Gash Bell villains have the occasional habit of breaking into song... songs that are quirky but usually made of awesome. For examples, watch Koral Q act like a tokusatsu hero. Kiees mangles Beethoven wonderfully. Gash's creepy stalker has the rare song that's good in both Japanese and English. And, of course, this trope would be horrendously incomplete without a certain V-shaped 1000-year-old melon-eating badass.
- The Yu-Gi-Oh! dub soundtrack has "Face Up, Face Down" sung by Pegasus.
- Revolutionary Girl Utena has very fitting music indeed for Akio. His theme song sounds like it's from a porn.
- Sailor Moon doesn't usually give the villains image songs, but they did for Galaxia. Her song, Golden Queen Galaxia is equal parts bitchin' guitar solo, jazz-tempo piano and evil harpsichord. Pretty badass overall.
- Queen Beryl also got a song as well (albeit it wasn't sung by her voice actress) but it is nevertheless meant to be Beryl's song about stealing energy.
- Manga example: Makube Rokuro has one in the second volume of Osamu Tezuka's Vampires, a devilish Disney Acid Sequence on paper.
- The Red Ribbon Army from the first Dragon Ball anime had its own theme.
- Rip Van Winkle from the fourth Hellsing OVA was fond of singing the German opera Der Freischütz. The YouTube clips seem to have her singing the hero's part -- O diese Sonne!. And when Alucard attacks her in the manga, he sings the demon's part.
- Jinnai Katsuhiko's very martial-sounding Image Song from El-Hazard: The Magnificent World is "Seifukuou Jinnai Katsuhiko", AKA "The Conqueror Jinnai".
- As Misa Amane (like her crush/master Kira) is a Knight Templar extremist with genuine "good guys" as enemies, her song in the Death Note episode "Silence" is technically a Villain Song of sorts - it focuses on hers and fellow villain Kira's support for each other (Kira is even mentioned as "God" in the song). Since Misa is no Card-Carrying Villain, the song is a soft, sentimental, simple ballad, and sounds like the thing that would normally be sung by a non-evil character (both Misa and Light genuinely believe that they are doing the right thing for the world). Not to mention the fact that she's singing it while killing people. The English version is here, and the original is here.
- Since "Mr. Grinch" counts, one may submit that the entire first opening theme to Death Note is, in fact, a villain song. When the lyrics are translated, they are essentially Light's philosophy and goal touted out for the world to see as the show begins. The difference, though, is that "Mr. Grinch" is sung by the Grinch himself.
- This video transforms "Prince Ali" from Aladdin into a full-on Villain Song for Gundam 00's resident Complete Monster, Ali Al-Saachez.
- Fushigi Yuugi gives us Soi's image song "Kooritachi no Pride"
What do you want? I'll snatch it from you
- From the same series, Yui's image song, "Aoi Arashi", wherein she sings of her desire to take revenge on Miaka and Tamahome:
I'll make it so / you alone will never be happy.\
- The Black Four from Kimba the White Lion have a catchy and somewhat surreal number about "doin' dirty business in style".
- Big Bad Miyo Takano of Higurashi no Naku Koro ni has a rather fitting Villain song in the Higurashi no Naku Koro ni Kai ~Character Case Book~ Vol. 2, Bon~Karma, with evil laughing, death threats and all.
- The Mobile Suit Gundam main rival, Char Aznable is given "Char ga Kuru" as his theme music, though it is not in the anime.
- Gundam ZZ has Silent Voice, sung from Haman's viewpoint towards Judau and company, used as the 2nd opening.
- In Rock Muscial Bleach, Aizen, Ichimaru and Tosen have one, spoken in Japanese with a mix of Gratuitous English, "Catharsis of Eternity."
- There's also the Bleach Beat Collections, three of which (at least) have the voice actor for the character singing two songs pertaining to their character. "Kyouka Suigetsu" by Aizen's is particularly haunting, while Ulquiorra's song is apt to his personality by title; "Crush the World Dow N". Grimmjow also has two songs, one titled "Br Ea K" and the other as "Six Feelings".
- In Yatterman, the Doronbo Skull Gang usually sings while building their new robots. Most well known of these numbers is "Tensai Doronbo", where they sing about how they love crime, are determined to grab the Skull Stones first, and how everybody loves them more. It pops up in the 2008 remake, and even the live-action movie.
- While there are no villains singing in Kinnikuman itself, EVERY villain has a villain song released on soundtrack. The villains themselves don't sing them admittedly, but it IS written as if they were the ones singing them, and they do give intros to the song, and sometimes even have spoken lines in them.
- Big Mom, one of the Four Emperors of the New World in One Piece, makes her on-screen first appearance in Episode 786 with a bizarre musical number that is a dark parody of thirties cartoons with singing flowers, trees, clouds and furniture. The 'Totto Land' musical number is juxtaposed with her minions attacking, slaughtering, trampling and committing senseless acts of violence against residents of islands simply to get ingredients for a tea party. Big Mom and her followers (many of which are the aforementioned singing flowers, trees, clouds, and furniture) continue to sing cheerily of the 'Tea Party From Hell' that they're planning, right up to the 'To Be Continued' screen.