Les Misérables has two, with Thenardier singing "Master of the House" and "Dog Eat Dog". (Three, if you count "Beggars at the Feast", which is the same tune as "Master of the House" but with new lyrics.) The primary (albeit misguided) antagonist, Inspector Javert, has the song "Stars".
"Master of the House" is an interesting one because it stands out as a moment of relatively light relief in a musical about rebellion, tragedy and romance.
The most villainous of all these possible Villain Songs might well be "Dog Eats Dog", in which Thenardier sings about the joy of robbing dead bodies. Unlike in some cases, this fails to seem like lovable roguery at all — it finally hits the audience in the face that Thenardier really is scum. And most of those he is robbing are essentially youths and children, two of whom are his own son and daughter.
And "Beggars at the Feast" is sort of a Villain Song in that it further outlines the Thenardiers' ideals and motivations (though by the point in the play when it's sung, their motivations are pretty well established). Singing to the Lord on Sundays, praying for the gifts he'll send, but we're the ones that take it, we're the ones who make it in the end!
"Stars", Javert's song, is an interesting version. Though Javert is the primary antagonist, his song is a very beautiful, melodic song about doing his duty to God and being a servant of justice; he doesn't see the motives or plans he's singing about as "evil". It can be played as confident and determined or softer and more humble depending on the actor. The implication is that though Javert may be not be a nice or good man by any stretch, he's notreallyevil. The tone contrasts well with "Dog Eats Dog", which is the REAL villain song of Les Misérables, identifying Thenardier as far more evil than Javert. One might even say that "Stars" is an Anti-VillainSong.
Every 'villain gets one in the Sailor Moon stage Musical adaptations, the Sera Myu. Some villains who were the baddies of multiple musicals got multiple songs, notably Queen Beryl and Sailor Galaxia. The two even SHARED a song, titled Yamikoso Utsukushii ~Galaxia no Iradachi~ (Darkness is Beautiful ~Galaxia's Irritation~) in one musical wherein Galaxia revived Beryl. (Or rather it was set up Beryl's original villain Group song, with additions of Galaxia snaking about how she's just using Beryl in the long run in the background) Villain songs in the Sera Myu generally fell in one of two categories: Songs for individual villains, and songs for the baddie group as a whole. An example of the former is Yami no Hitsugi (Coffin of Darkness), which is all about Queen Beryl, while an example is the original Yamikoso Utsukushii which was for the Dark Kingdom as a whole and their Evil Plans. When a villain shows up in a later (unrelated) musical they sometimes get a new song, sometimes they re-use an old one. Rarely a villain could also share a theme with a Senshi, an example of this rare type is Onna no Ronsou (Dispute between Women) which was sung between Sailor Pluto and Queen Beryl describing how they were similar and their shared unrequited love for Mamoru.
"The Mad Hatter" and "I Will Prevail" sung by, you guessed it, the Mad Hatter in Wildhorn's "Wonderland", a musical adaptation of Alice in Wonderland. Because, you know, high notes higher than Alice's mean the Hatter is obviously evil. "Hatter" serves as an eponymous introduction song, while "I Will Prevail" opens act two with a bang —and more Incredibly Long Notes.
Similarly, the manic milliner struts her manipulative side when she entreats Alice's daughter Chloe to join the Hatter and her minion on "A Nice Little Walk".
"It Ain't Necessarily So" and "There's a Boat That's Leaving Soon For New York," Sportin' Life's songs mocking a sermon and tempting one of the protagonists to a life of vice respectively, from Porgy and Bess.
Assassins has a ton of them, appropriately enough for a play about presidential assassins. "The Ballad of Booth", "The Gun Song", "The Ballad of Czolgosz", "The Ballad of Guiteau" and "Another National Anthem" are all unusual variants of the standard Villain Song. The most iconic villain song of the musical is "Everybody's Got The Right", a irony-tainted song where the assassins proclaim everybody has the right to pursue the American Dream through any means neccesary...including presidential assassination.
Probably the most unusual villain song in the musical is "The Ballad of Guiteau", where the villainous Charles Guiteau sings a demented hymn as he tap-dances up to the gallows. What makes it unusual is that the lyrics are taken from a poem that the real Charles Guiteau wrote on the way to his execution; Stephen Sondheim simply set it to music.
Well, Guiteau's continual "I am going to the Lordy/I am so glad" refrains are. The Balladeer's lines, obviously, are written by Sondheim.
Judge Turpin also has a Villain Song, though it's sometimes cut. Probably because, well, he's whipping himself and praying in between lusting after Johanna (suggesting that he practices self-flagellation or is just a freaky masochist). Programs and cast albums usually list this song as "Johanna", but it has no musical connection with Anthony's love song "Johanna" in the first act (which is the one performed outside the show under that name), or the "Johanna Sequence" in the second act, which includes a portion of the earlier "Johanna" in between new verses which Todd sings to himself as he offs his customers.
"A Little Priest" also fits the rules for a villain song: where "Epiphany" describes Todd's violent reaction to an awful world, "Priest" is Mrs. Lovett's refinement of the idea into a practical ("yet appropriate as always") course of action. And also contains justifications for their awful scheme: "save a lot of graves, do a lot of relatives favours" for instance.
Parodied in The Mikado with "I've Got a Little List". The scary executioner gets a Villain Song — and in the next dialogue scene, we learn he's a spineless wimp who is terrified of killing.
Except that the executioner is more of an Anti-Hero. The primary villain song is probably "Your revels cease - O Fool, that fleest my hallowed joys", sung by Katisha.
The Pirate King gets his number "Pirate King" which is all about how awesome it is to be a Pirate King. Naturally he's something of an Anti-Villain.
And there's a short one with Pirate!Ruth about how they're going to kill the Major-General and his daughters, called Tonight He Dies.
"Progress is the Root of All Evil" from the musical adaptation of Li'l Abner.
"The Seven Deadly Virtues" from Camelot. Also, the knights have "Fie On Goodness" after their collective Face-Heel Turn, in a number dropped from many productions (the original Broadway production dropped it just after its inclusion on the cast album).
Since the Phantom is turned into an even bigger Woobie in the Arthur Kopit/Maury Yeston take on the story, he doesn't even get that much (except perhaps his Villainous Breakdown towards the end of "Christine".) Carlotta, however, has the gloating "This Place Is Mine".
The Trans-Siberian Orchestra Rock OperaBeethoven's Last Night has two: "Mephistopheles", where the titular demon proclaims himself "god of second chance" while trying to cut a deal with Beethoven, and "Misery", when Mephistopheles gleefully threatens to maim, cripple, torture, and eventually kill a child if Beethoven doesn't give him what he wants. Both get sung way over the top, with much scenery-chewing and Large Hammery.
TSO also included an equally hammy Villain Song in their album The Lost Christmas Eve: "What is Christmas?", sung by the Scrooge-like antagonist.
"Don't Nobody Bring Me No Bad News" is the mantra of Evilene, the Wicked Witch of the West, in The Wiz.
The Cellblock Tango in Chicago. Awesome song, mood lighting, and girls prowling around in leather underwear talking about how their murders were completely justified.
He had it comin'!
Of course, the innocent Hungarian prisoner's verse states her guiltlessness for real, and of course she's the only one who pays for it. Crapsack World indeed.
From the same musical, "All I Care About is Love", sung by Billy Flynn. The entire song is a lie. Although he's sort of an antihero.
An even better example for Flynn is "Razzle Dazzle", where he gleefully gives a show-stopping number about getting away with anything by using pure showmanship.
Almost every song from Chicago (except for "Mr. Cellophane" and "A Little Bit of Good" (sung by Mary Sunshine in the show)) could be considered a Villain Song, as almost all of the main characters are murderers or corrupt.
Notably averted in Wicked. Fiyero's song "Dancing Through Life" is a textbook cackling song about his nihilistic philosophy, but he turns out to be a much better person than he seems. The Wizard's song, "Wonderful", is the very opposite of a standard Villain Song: he's trying to justify his crimes by playing humble and innocent, and (unlike The Sound of Music) is still the Big Bad. Elphaba (the heroine and titular Wicked Witch) even gets one in "No Good Deed", but it's undercut by the fact that she's rocketing through the stages of grief and has some full blown Sanity Slippage/Heroic BSOD going on by the end. Despite her big talk, she never can bring herself to be the villain. Finally, "Wicked Witch of the East" can almost be read as one, except that Nessarose is mourning the fact that she somehow became the villain without noticing.
From Hairspray, "(The Legend of) Miss Baltimore Crabs". Front step, cha-cha-cha... There's just something about that one line that screams "you're walking into the serpent's lair". Michelle Pfeiffer even said she signed on for this one song. It's not hard to see why.
Her daughter Amber has "Cooties", a mean-spirited Take That song not-so-subtly directed at Tracy.
Macavity, the levitating crimelord cat from Cats. His song (though he doesn't sing it himself) is a lengthy paean to his Magnificent Bastardry, and is likely the one song besides "Memory" that is most remembered from the play.
Most songs from The Black Rider: The Casting of the Magic Bullets are pretty creepy, but Pegleg gets in three songs of his own: "Just The Right Bullets", "Flash Pan Hunter", and "Gospel Train".
Since Woyzeck has so many villains, each one gets their own song: the Doctor has "God's Away on Business", the Drum Major has "Another Man's Vine" and a creepy duet with Marie called "Everything Goes to Hell", and the Captain gets "Starving in the Belly of a Whale".
"The Soviet Machine" from Chess, sung by Molokov and the KGB Agents.
"Difficult and Dangerous Times", also titled "US vs. USSR" (formerly a part of "Opening Ceremony"), which is basically a villain song for Cold War politics in general.
But we're gonna smash that bastard! Make him wanna change his name— Take him to the cleaners and devastate him Wipe him out, humiliate him...
The Engineer's ode to America's love of depravity (and his love for that) in "The American Dream" from Miss Saigon. "If You Want to Die In Bed" also counts as it spells out his goal to save his own skin. Actually, anything the Engineer sings might fall under this trope...
Hyde has "Alive" from the Jekyll and Hyde musical.
His half of "Confrontation" definitely counts as well:
"You can't control me! I'll live deep inside you! Each day you'll feel me devour your soul!"
He also twists two other songs into Villain Songs: "You and Me and Pokémon" and "Everything Changes".
Team Rocket got a subversion of the traditional Villain Song called "The Best at Being the Worst", centering around their own incompetence at what they do.
"Double Trouble" could also count, which has Team Rocket showing enjoyment of being bad guys. However, this originally had a longer version of from a CD the show put out which had several other songs that were in the musical, including "Misty's Song" and "Two Perfect Girls".
"Cool, Cool Considerate Men" from the musical 1776 lays out the reasons Dickinson and his supporters don't want independence: they're comfortable as they are, they don't want to put their wealth and property at risk for a cause they think can't win, and they think the common man will follow them because they're pretty cynical about him. It's accompanied by a big dance number on the floor of Congress.
"Molasses to Rum" for Edward Rutledge, which is also him saying that the South and the North are Not So Different—they both, in different ways, participate in and profit from the slave trade. Therefore, not only must the anti-slavery clause be removed from the Declaration, the Northerners are absolute hypocrites for wanting it there in the first place.
"Falcon in the Dive" from the musical adaptation of The Scarlet Pimpernel (which conveniently comes after the main heroic song, "Into The Fire", in the libretto).
"It's All About The Green" in the musical adaptation of The Wedding Singer - though Glen is more of a Jerkass than an outright villain, and there are cooler songs in "Casualty of Love", "Today You Are A Man" and others, it's still right up there.
In Urinetown, several songs go to the bad guys, including "Cop Song" which goes to the henchmen as well as "Don't be the Bunny" and "Mister Cladwell" going to the main villain Mr. Cladwell. The latter of which is an outright song praising his virtues (Mister Cladwell, you're so Godly/oddly perfect and right).
Anyone Can Whistle has several songs for the evil Mayoress Cora Hoover-Hooper. The best of these is the first song of the show, "Me And My Town", in which she laments her 0% Approval Rating.
Not to mention Big Bad's performances of Killer Queen and Another One Bites the Dust.
Miles Gloriosus' "Bring Me My Bride" in A Funny Thing Happened on the Way to the Forum.
Oliver! has several Villain songs: Big Bad Bill Sykes gets "My Name" and the Affably Evil Fagin actually gets two, "You've Got to Pick a Pocket or Two" and "Reviewing the Situation" (in the reprise especially). That Fagin gets more than the real villain isn't too surprising though, since the role is usually played as a Large Ham.
In Annie, Miss Hannigan expresses her hatred for children in "Little Girls"; later, she is joined by her sleazy brother Rooster and his airhead girlfriend for the song "Easy Street".
"Let Things Be Like They Always Was" from Street Scene is less of a song than a Puccini-like aria, but it certainly sounds dark and menacing. It's Mr. Maurrant's only uninterrupted solo, in which he gives vent to his bitter reactionary attitude.
John Howard's dark and menacing march "Power" in Keating!. Which is then hilariously contrasted with "The Mateship".Whether he's a villain in Real Life depends which side of the political spectrum you're on, but he definitely qualifies in the musical.
The little-known German musical Hexen has "Gleich", sung by the Magitech witch Clony, whose magic borders on Mad Scientist territory. Clony doesn't consider herself evil and really thinks she's doing humanity a favor by giving everyone armies of clones of themselves to do all the work, but she is nevertheless an unabashed egotist who gets a huge rock number in which she praises her own intellect, style and superiority over everyone else. Not to mention that the plan she's explaining is essentially one for slavery.
Tanz der Vampire has Ewigkeit, in which a whole chorus of vampires rises from their graves and plots to make humanity as miserable and insane as they are. It happens to be the most chilling song in the whole musical.
Sophie in Elisabeth, as more of a Knight Templar than a really sinister villain, has the rigid "Eine Kaiserin muss glanzen!" ("An Empress Must Sparkle!"), in which she bullies her newly-married daughter-in-law into (temporary) tears and submission. Later on, though, she sends her son to a brothel to weaken his marriage, and the shady madam and prostitutes' song "Nur kein genieren" ("Don't Be Ashamed, Dear") fits into this trope fairly well.
There's also the bouncy "Kitsch", which serves as a villain song for the murderous, sarcastic Lucheni and as a kind of The Villain Sucks Song for the selfish Elisabeth as well as all of her fawning, devoted subjects- including the audience.
"Der letzte Tanz" may count, considering it is a personification of Death showing up to menace Elisabeth at her wedding, gloat about how he'll win her in the end whether she likes it or not, and basically stop the show.
The Spider Woman isn't so much the villain of that show as a character's nightmare. A better villain song would be "Lucky Molina".
"I'd Rather Die on My Feet Than Live On My Knees" for Thomas in The Beautiful Game. The song is short and Thomas isn't exactly a show stopping villain, but it's extremely effective in vilifying the guy. For the majority of the show he was a misguided jerkass, but not worse than some of the others.
Also played with in "Come Up to My Office", which is sung by Leo Frank, but is actually a fabricated account on the part of the prosecution.
Mozart! (from the same creative team as Elisabeth) features a mute villain- Mozart's own genius, portrayed a a demon/Creepy Child in the shape of Mozart himself at age six or so that follows the adult Mozart around, constantly composing and using Mozart's blood as ink. Thusly, the big showstopping Ear Worm villain-song-stand-in goes to Archbishop Colloredo, who's more of a petty annoyance than anything, in the form of "Wo Bleibt Mozart?" It's still pretty grandiose and nasty to the title character.
Notable in that it's the very first song, so as to leave no doubt as to whom the Bad Guy is supposed to be. "We'll forge a check, or cut your neck, if we can make a dime!"
Radames' father, though not the main villain of Aida gets two: the standard "Another Pyramid" and "Like Father, Like Son", which Radames tries to turn into a The Villain Sucks Song. He fails.
There's also "Herod's Song", another seriously catchy number.
Norman Jewison's film version also adds "Then We Are Decided", which figures as both another Villain Song and an "I Want" Song for Caiaphas and Annas.
Draco's "Back To Hogwarts" solo from A Very Potter Musical can be quite evil, considering that he's a short woman in a blonde wig playing a delusional pratfaller twelve-year-old boy in a comedy/parody. Needless to say, the delivery is brilliant.
Look out world, for the dawn of the day When everyone will do whatever I say And that Potter won't be in my way, and then I'll be the one who is totally awesome!
Voldemort gets a second song after his resurrection, entitled "Dance Again" which culminates with him and the Death Eaters doing a kickline.
Umbridge's showstopping number "Stutter" from A Very Potter Sequel. The Dementor back-up dancers have to be seen to be believed.
The first song "Not Over Yet". It is sung by Lucius Malfoy, outlining his plan to prevent Voldemort's defeat by using a Time Turner to kill Harry in his first year of Hogwarts.
Our history is nothing more than what the losers settle for.
In Starship, Pincer has "Kick it Up a Notch". It is later reprised by Junior.
"Rogues are we" from Holy Musical B@man.
In the 12th century liturgical drama, the Ludus de Herode, Herod and his son have a duet, Salve, pater inclite, in which they threaten the newborn Messiah.
Turnabout Musical, the up-and-coming musical adaptation of Phoenix Wright, has some good ones in the making: Winston Payne's comical "Rookie Killer", Redd White's diabolically catchy "Redd White and You" (a plain-clothes rehearsal can be seen here), and Manfred von Karma's appropriately haunting, though strangely baritone, "Anything to Win" — Ominous Latin Chanting included. Fortunately, the "hero songs" are very much a match for them.
Salieri in Mozart L'Opera Rock has several songs, but perhaps the best example of this trope is "Le bien qui fait mal", which is all about how he's "EnvoĂ»té par des idées folles/Bewitched by crazy thoughts", and "Je sens de violentes pulsions/I'm feeling violent impulses", oh and "Le désir devient ma prison/Desire has become my prison". Salieri's clearly losing it.
"One Touch Of Alchemy" in Knickerbocker Holiday, the culmination of Stuyvesant's New Era Speech. Shortly after, he has a duet with one of his henchmen, "The One Indispensable Man".
The true antagonist of Next To Normal is mental illness, but a secondary villain is Gabe, who certainly enables Diana in her mental illness (and even leads her into a suicide attempt, in "I Dreamed A Dance"). His song "I'm Alive" and its extremely Dark Reprise could be considered Villain Songs.
If you consider Gabe as an avatar for Diana's mental illness the song gets even darker.
A brief, out-of-context clip attests that Enron has at least one good villain song with Jeff Skilling's "Primetime for Skilling". ("I'm the boss, here's the gist; I'm the guy who gets to lie to analysts...") Actually, at least half of the twenty-six songs listed sound like contenders.
In both the movie and musical versions of Evita, Che (who isn't quite the villain, but he's close enough) has "Oh What a Circus". There's also the short and sinister "The Art of the Possible" with Peron, and the fantastic "Waltz for Eva and Che" with, well, guess.
Groovelily's musical Sleeping Beauty Wakes has some marvelous villain songs by the Evil Fairy: "Uninvited", about not being invited to the celebration of the princess' birthday, and "The Wheel Goes Round", sung when she's in disguise trying to lure the princess to the spinning wheel.
They move in the shadows where no one can see And they're chainin' up people and they're bringin' em to me askin' me, "Kill them NOW, or LATER?" Askin' ME! "Kill them now, or later?" Noon by the clock, and so still by the dock You can hear a foghorn miles away And in that quiet of death, I'll say, "Right now." Then they'll pile up the bodies And I'll say, "That'll learn ya!"
Even though It's a parody to a Fiddler on the Roof, A Shoggoth On The Roof has some pretty dark tunes. Turning famous songs into a Lovecraftian induced musical. A lot of these can be considered villain songs in their own right, but the one the takes the cake is easily "Do You Fear Me?" which is sung by... Cthulhu himself! Even though The Nightmareis a close runner up due a portion of it dedicated to The Ghost of Lavinia Whately singing about her plan to have her two sons raping Armitage's daughter Prudence with Tentacles!
Audrey II from Little Shop of Horrors got "Feed Me" and "Suppertime". From the same musical, Orin had "Dentist!". In the film version and some productions, there is a song called "Mean Green Mother From Outer Space" for Audrey II. There was also a Cut Song for Audrey II titled, simply, "I'm Bad". Furthermore, a little-known Cut Song from the stage version, a reprise of "The Meek Shall Inherit", would have gone to Patrick Martin, the man that sells the plants across the nation and thus brings about the end of the world.
"The Meek Shall Inherit" is already pretty sinister; even if they don't know they're doing it, the singers are encouraging Seymour to kill more people so he'll be famous.
"Z: The Masked Musical" (which never got past the concept album stage) featured the alcalde's delightful "Glorious, Gluttonous Greed", in which he recounts his love of money, revels in the suffering of the peasants, describes his plan to purchase a noble title, and demonstrates the ability to count and identify coins just by the sound they make hitting the table. The rest of the album is execrable.
Seussical (That's right, there's a Dr. Seussmusical) has General Ghengiz Khan Schmitz's "The Military Academy" and Mayzie's "Amazing Mayzie". The Sour Kangaroo doesn't have one, oddly, despite being the main antagonist, although she does have some lines in "Biggest Blame Fool" which could count.
The original version of Starlight Express had "C.B." the gleeful confession of a serial killer caboose. It makes sense in context.
While the character of Greaseball is not anywhere as villainous as C.B. his introductory number "Rolling Stock" still counts.
Electra's introduction song, "AC/DC", is another example.
"Forever Yours" from Once On This Island is a bizarre half-love ballad-half-Villain Song, taking on the latter quality after Papa Ge joins in. "Your life is forever miiiiiiiiiiiiiiiiine!" Actually, each of the Jerkass Gods gets a song, though "Forever Yours" is the only actively villainous one. Rich Bitch Andrea sings for a bit, too.
The 1980's Broadway musical Drood is notable here in that it has nine possible villain songs: Two which are always in the show ("A Man Could Go Quite Mad" and "Jasper's Confession") and 7 possible murderer confessions decided by audience vote. Some may not count, however, as at least one is a joke about how unlikely that particular character being the murder is.
The Toxic Avenger Musical has the song "Jersey Girl" sung by the mayor of New Jersey, Babs Belgoody. Immediately after that song, the mayor gets another one along with the town bullies called "Get The Geek".
Flash Thompson and his cronies have "Bullying by Numbers" and "Venom".
Before the show was revamped, second-act villain Arachne had two as well; "Think Again" lamenting Peter's decision to give up his Spider-Man identity, and "Deeply Furious" an absurd and much mocked song about shoes.
The Green Goblin gets three. As Norman Osborn he sings "DIY World", about how designer genes are the way of the future. Not blatantly evil, but we know what happens. As the Goblin, he sings "I'll Take Manhattan", a loungey evil song, and a "A Freak Like Me Needs Company" (derived from a recurring line in "Deeply Furious") about his creation of the Sinister Six.
The main antagonist of Queen's Rock OperaWe Will Rock You is called Killer Queen. Naturally she's introduced with the song of the same name. "Flash" might be one for Khashoggi.
Khashoggi's rendition of "Seven Seas Of Rhye" is also highly villainous.
Older Than Feudalism: A significant chunk of Aeschylus' Theatre/Eumenides is the villain song of the Erinyes, where they seek to justify the Revenge they enforce and boast of how terrible and powerful they are, while disdaining the injustice of the Cycle of Revenge that is the plot of the story.
From Sister Act: The Musical, the Big Bad and the Quirky Miniboss Squad both get one. "Lady In The Long Black Dress" is sung by the Miniboss Squad and is about seducing the nuns of the convent. "When I Find My Baby", sung by the Big Bad, is about how he will find Deloris again and "shoot that girl! And then I’ll stab that girl, and then I’ll take her and shake her, and make her meet her maker!"...
The Austrian Musical Rudolf – Affaire Mayerling about the life of Rudolf, Crown Prince of Austria before his very early suizide has Count Eduard Taaffe, the Austrian Emperors closest advisor, sing a very intense song about how politics are easy if you pull the strings behind the curtains and how as advisor to the Emperor, the whole world bends to his will if he demands it. The Aristocrats and even the emperor dance as his puppets underneath and are shown to listen to his advises. There is also an "English Version" but the "German Version"is much faster and far more powerful. It is a little ironic to listen to the song when you have in mind that later during his ministry Austria went into WW1 and therefore lost most of their political clout as a nation for a long time.
The Italian work The Bethrothed Lovers Modern Opera: Jesus Christ, where to begin?
First of all, the Ouverture gives us a glimpse of Don Rodrigo's song, "What is this fire?". That's right, the very introduction is interrupted by the villains singing about his evil goal.
The third song, "It has not to be done", features the Thugs (led by the Griso), threatening Don Abbondio, the town priest, saying that it will end bad for him, shoulf he ever marry the titular bethrothed. It's mostly intended as comedic, especially when they mock him, but it is still frightening when you realize that, in a time and place that saw Vatican at its maximal power, Don Rodrigo is not afraid to threaten a man of Church.
The fifth one, "Going... fleeing... the power" starts off with just Don Abbondio establishing once again his lack of guts, but when he goes to sleep... he actually dreams about Don Rodrigo, on top of a skull-decorated spider-web, who nonchalantely plays with a rapier, all while representing the embodiment of the very concepts of power and arrogance. He didn't even appear in the story, yet, and he is already established as a guy not to be messed with. In this particular piece, he sings about how he can walk at his will over people heads, and how he is everything while Don Abbondio is nothing. And now picture such a self-centered bully played by the same guy who played Quasimodo.
The eighth song, "Law is the same for everybody", is one of the funniest and, ironically one of the most evil. In it, the lawman Azzeccagarbugli (lit., Mischief-finder, which in Italy has become a nickname for every corrupted lawperson) sings about how it is his job to use law and justice to help people, while he means his "help" actually is avoiding criminals to pay the price of their crimes. He even accuses Renzo (the lead male character) of being a criminal, for daring to suggest to go against Don Rodrigo.
The eleventh song, "Wine, wine", sees for the first time Don Rodrigo. With all of his friends (other noble bullies), he playfully spars with swords and sings about the joy of drinking fine wine in company on the day of St. Martin. Then he casually mention he will subjugate and tame Lucia, just as a bet with a friend of his, and the song ends with them all gloating about the even bigger joy of having their way with women.
Right after, "There will be a day" is mainly sung by one of the most importants good characters, Fra Cristoforo, and is about how God will not be pleased with that power abuse against the weakest. Then, Don Rodrigo interrupts, insulting Fra Cristoforo and telling him to watch his tongue. Ironically, the truly frightening part of this song comes from Cristoforo himself, who pretty much curses Don Rodrigo, telling him God will annihilate him. And the scary part is... it actually happens.
Then we have "The nigh of Mischieves", in which the main characters try to trick Don Abbondio in marrying Renzo and Lucia. But there is also the Griso, with other thugs, singing in a magnificent barithonal voice of how they are going to kidnap Lucia and how Don Rodrigo will be proud of them for such an act.
Just when we heard five songs about the good guy, and we were starting to lose hope about the amount of villainy, we have "St. Martin has arrived", a reprise of "Wine, wine", really similar but with an even better coreography, with much more swordsmanship and every background character groping at least one maid during the number.
It is immediately followed by the aforementioned "What is this fire". A song so full of pathos and sexual depravity, it could give "Hellfire" and "Your love will kill me" a run for their money. Yeah, you read it right: a song so lustful Frollo seems tame in comparison. Especially creepy when Don Rodrigo sings "Never you will tell me 'stop!', you, who now are saying 'never!'"; he basically says he will continue to rape Lucia until she forces herself to enjoy it. Jesus Christ. And, no, it was not added for this adaptation: even in the original novel, he betted he could have the ius primae noctis, and the only thing added in this version was that here Don Rodrigo actually lusts after Lucia, instead of seeing her just as a bet. It's hardly any better.
"The Griso has returned", which immediately follows, is both yet another reprise of "Wine, wine", and, in the second part, one for the thug's part in "The night of mischievs". Don Rodrigo doesn't want to accept his defeat, and he bets all of his wine he will have Lucia before the end of St.Martin's day. Then The Griso arrives empty-handed, getting properly bitchslapped.
"Let's violate the clausure", just two songs away, starts of as just the hammiestbadass boast in the history of musical villainy, with the thugs claiming they will attack the convent and take Lucia. Then, Don Rodrigo cuts their bullshit, and gives a dark reprise to one of Fra Crisotoforo's song, announcing he knows who he has to talk to. Immediately this certain someone is described as almost more a force of nature than a man: the Unnamed.
"The unnamed" is right after that, and it is pretty much a glorification of that guy. He starts by singing about he enjoys life because death itself is his trusted companion, and they are against everybody and everything, not caring about the existence of something as futile as a law or even God Himself. His henchmen (some creepy black-cloaked things), even call him "The black shadow, the fear". Then we see Don Rodrigo, who has alway been arrogant and full of himself, pretty much begging the Unnamed to help him; he responds by saying "that convent has no door, has no gate and has no wall", while his thugs reply "all is open at His will, each and one defense will fall!". The song ends saying that the Unnamed holds a limitless power, which makes him master of every fate, and that he can destroy without a move fear, life and death. Keep in mind that this is a realistic setting, so he has no supernatural power whatsoever: he is just that feared, that ruthless and that competent. Plus, he is played by Vittorio Matteucci, who was Frollo in "Notre-Dame de Paris" and Dracula in "Dracula Opera Rock"; probably, when he cuts himself shaving, he bleeds awesome assholeness.
Immediately after, we have "Let her out": the Kite (the Unnamed's elite mook) has sent Egidio, the lover of Monza's Nun, to convince her to send Lucia out, so that the thugs may abduct her, bring her to the Unnamed, and then give her to Don Rodrigo.
"The Lansquenets, the letters". Cannon sounds, blood-red lighting, and an arm of mercenaries marching through Milano, singing a creepy cross between a Church chant, a Nazi parade anthem, and that thing the Uruk-Hai sung in the Bakshi "Lord of the Rings" movie. If anybody studied history, they'll know what exactly the Lansquenets did. If nobody did, don't worry: while they do their war chants, Renzo provides an explanation, saying that they are a scourge devastating the fields, burning the houses, murdering everybody, raping women and bringing the plague, to top all of that; the song itself ends with Renzo repeating "The Plague!", echoed by the Lansquenets in German. All is made especially creepy when you realize that is what Renzo is dictating to be written in a letter to Lucia, to tell her he hopes to make it out alive to see her again.
"The Betrayal", the last villains song, sees Don Rodrigo dying by plague; there is no make-up to simulate the symptons, but Giň di Tonno acually seems febricitant, trembling and ill; plus, he has a vision of what Fra Cristoforo has shown him, and feels he si being crushed by rhe rightful wrath of the Allmighty. He send the Griso to call a doctor, but his thug returns with some jackals, to take him away and steal his fortune. Ironically, the Griso gets infected and dies before he has to change to spend a single coin of what he stole.
The theatrical version of Newsies gives Joseph Pulitzer the song "The Bottom Line", wherein he explains why he's boosting the price of his papers, and how he doesn't care how it'll affect the newsies. He gets a reprise in Act 2, when he threatens to have all the newsies arrested if Jack doesn't tell them to end the strike.
It's A Bird, It's A Plane, It's Superman has the song "Revenge", in which Dr. Abner Sedgwick recounts all the Nobel Prizes he's been robbed of and says he'll destroy Superman to show the scientific community.
The closest thing to a villain in How to Succeed in Business Without Really Trying is Smug Snake Bud Frump, and his reprise of "The Company Way" and Dark Reprise of "Been A Long Day" arguably qualify for this, the former being a self-congratulatory number about how great he is (for being made head of the mailroom) an the latter sung as he puts his Evil Plan into action through blackmailing his uncle.
"The Apple Tree (Forbidden Fruit)" from The Apple Tree. The first act of the musical is based off of Mark Twain's Adam and Eve story. Probably the first villain song ever, it's sung from The Snake to temp Eve to take a bite from the apple.
Also if you count the King from the second act, he has a short musical piece "Barbara, how could you?" It's only about 10 seconds long. It's his reaction to seeing his daughter in love with a forbidden lover. He also sings a small solo in "Which Door?"
"The Stepsister's Lament" from Rodgers and Hammerstein's Cinderella. Long before they even sing the song, the tune is the stepfamily's theme song and plays during some of their entrances.
"Opportunity" and partially "It can't be true" from 13.
Drood has "A Man Could Go Quite Mad", introducing John Jasper and his repressed insanity. Any of the murderers' confessions could count as well.
The Lady Pirates of Captain Bree has the title song for the title character though she does a Heel-Face Turn later on and "A Lady of Sensibility" for the resident Rich Bitch, both of which double as I Am Songs.
"Spread A Little Sunshine" in Pippin, in which Fastrada plots to get her son closer to the throne while (sarcastically) singing about following the Golden Rule.
The Broadway musical version of Matilda has "The Hammer" and "The Smell of Rebellion".
Charlie and the Chocolate Factory uses this trope to an unusual end. The four bratty kids and their parents aren't villains, so their establishing tunes fall under the "I Am" Song trope, though Mike's verses in "It's Teavee Time" overlap with a villain song as he proudly declares that he cheated to get his Golden Ticket. But the show does have a glamorous, Large HamAnti-Hero: Willy Wonka. His first song "It Must Be Believed to Be Seen", which doubles as the Act One finale, is a Welcoming Song and an I Am Great Song lyrically, but musically and visually it's this trope — brassy, intense, cheekily sinister, and catchy. There's Spontaneous Choreography for the Golden Ticket winners and the press, the scenery's awash in colorful light by the end...and all along, only the audience suspects/knows that the enthusiastic tour group is going to get a lot more than they bargained for in Act Two.
In Twice Charmed, Wicked Fairy Godfather Franco DiFortunato gets "It's Never Too Late."
"It’s never too late to plan a wicked plan~ Smash both of her shoes and make off with her man!"
Most of the songs in Thrill Me are this. Chronologically: "Nothing Like a Fire" is Richard glorying in the warehouse fire he just set, and seducing Nathan; "A Written Contract" is Richard getting Nathan to agree to continue helping with his crimes "no matter what degree" and gloating about their superiority; "The Plan" is Richard excitedly plotting a murder; "Roadster" is Richard luring a twelve-year-old to his death; "Superior" is Richard gloating about being...superior to everyone else; and "Life Plus 99 Years" is Nathan gloating about having strung Richard along through almost all of the show. And really, there are arguments to be made for most of the other songs.
In Pokemon The Mewsical, Giovanni gets "To Be Boss" and "Finally," while Team Rocket gets "The Plan." Gary gets several villainous parts as well in different songs.
The villain song from "Tumbleweeds" (a musical written to be performed by students) has the title "It Feels So Good To Be Evil" and consists of the various villains gloating about exactly how much they love being villains.
The Winx Club musical Winx Power Show gives us "Non c'č Amore" ("There's No Love"), sung by Trix about their intention to destroy the Winx (or fight forever if they fail) and become invincible and the fact there's so much rage inside them that no love can redeem them.