Villainous Lament

But my dreams, they aren't as empty
As my conscience seems to be...
I have hours, only lonely
My love is vengeance
That's never free...

—"Behind Blue Eyes", by The Who

It's been said that the villain tends to have the best songs in any given musical, full of flash and gloating. But sometimes, the villain (or perhaps a Villain Protagonist, Anti-Villain, or character who made a Heel Face Turn) has a moment onstage in which they list all of their misdeeds or mistakes... and the audience realizes that the character really, really hates themselves for what they've done, and the song has clearly strayed from fully villainous territory.

Examples of Villainous Lament include:

Animation-Western

• "Jack's Lament" from The Nightmare Before Christmas is about how he's basically unhappy with the dark side.
  • Though it should be noted that Jack isn't evil, nor the villain. He's actually the hero of the story, and plays an integral role in rescuing Santa Claus from the downright nasty bugbag known as Oogie Boogie. It is his fault that Santa is there in the first place.
  • Keeping in mind that Jack isn't evil nor the villain, the first half of "Poor Jack" could count, too.
• Sideshow Bob had a plan to kill Krusty the Klown, and he was about to see the plan come to fruition when Krusty sang a song about how he really missed working with Bob. In turn, Bob sang about how he would really miss Krusty when he had killed him, and this made him have second thoughts and prevent his trap from killing Krusty.

Fan Works

• Potter Puppet Pals: "Have you ever had a bad day? Do you know what they'd call you if every day of your life was like that? They'd call you Snape..."
  • Except Harry's more the villain in Potter Puppet Pals - Snape's more the Butt Monkey.

Film

• "I'm so Ronery", Kim Jong Il's song in Team America.
• Dr. Frank N Furter's final song in The Rocky Horror Picture Show, "I'm Going Home."

Frank: Everywhere it's been the same... feeling... Like I'm outside in the rain... wheeling... Free, to try and find a game... dealing... Cards for sorrow, cards for pain...

• "Marley and Marley" from The Muppet Christmas Carol, wherein Jacob (and Robert) Marley narrate how it took suffering in the afterlife to realize their misdeeds while living.

"There was that time we evicted the entire orphanage!"
"I remember them standing in the cold with their frostbitten teddy bears!"
"Doh-ho-ho-ho! *shudder*"

• "Up there" from South Park Bigger Longer and Uncut. Who would have known Satan could be that woobieish?

Music

• Doctor Steel's "Lament for a Toy Factory".
• Twisted Sister's "Burn In Hell": "You can't believe all the things I've done wrong in my life / Without even trying, I've lived on the edge of a knife...."

Professional Wrestling

• Edge's theme, "Metalingus", was a really twisted inversion, or maybe just a subversion. It's a song about a Christian triumphing over personal shortcomings through faith in God....but Edge started using it after he became so obsessed with winning the WWE Championship that the desire turned him into a villain. So he basically saw championship gold as his "salvation" - even if he had to betray his tag-team partner and screw and corrupt his rival's girlfriend along the way.

Theater

• Both of Tybalt's songs from Gerard Presgurvic's Romeo et Juliette", but especially "C'est pas ma faute".
• "Die Unstillbare Gier" from Tanz der Vampire, in which both the audience and Alfred realize that Count von Krolock is a person, capable of great longing and regret.
• "No Good Deed" from Wicked.

Sure I meant well
Well, look at what well-meant did!

• "Accursed All Base Pursuit" from Gounod's Faust. Yep, an actual operatic example.
• "If I Can't Love Her" from the Screen to Stage Adaptation of Beauty and the Beast.
• "The Madness of King Scar" from the stage version of The Lion King.
• Javert's Soliloquy from Les Misérables.
• "Rudolf, wo bist du?" from Elisabeth.
  • Not a straight example as Elisabeth, who sings the lament, isn't the villain. While not an entirely likeable person, she is in fact the protagonist. A better example is "Bellaria," sung by the Archduchess Sophie, in which we find that the domineering, cruel woman we've seen her as until now has given everything for her son.
• "I Loved Her, Too" from Street Scene.
• "The Bum Won" from Fiorello!, in which a group of Tammany hacks read the headlines and weep.
• "Reviewing the Situation" from Oliver. Fagin wonders whether he should give up crime and make an honest man of himself.
• "Those Canaan Days" from Joseph and the Amazing Technicolor Dreamcoat. Marks the brothers' Heel Face Turn as they realize they miss Joseph.
• "Behind Blue Eyes" by The Who was originally intended as a villain's lament within Townshend's aborted Rock Opera Lifehouse.
• "Best at Being the Worst" from Team Rocket in the Pokemon Live! musical.
• "Pore Jud Is Dead" from Oklahoma!! counts as both a VillainSucksSong and this—Judd is a really self-loathing person, and even though Curly is insulting him in the song, he likes the idea that if he killed himself, people would feel sorry for shunning him.
• In Li'l Abner, General Bullmoose has "Progress Is The Root Of All Evil," a lament for plutocracy lost.
• "Call From The Grave" and "Epitaph" from Bertolt Brechts The Threepenny Opera. (Titles vary depending on the translation - "Ruf aus dem Gruft" and "Grabschrift" are the original titles.)
• It's kind of hard to pinpoint a "villain" in Evita, but all three main characters do villainous things and have songs where they regret something. Eva has (depending on the production) "Another Suitcase in Another Hall" (about people taking advantage of her) and "You Must Love Me" (showing her love for Peron). Che has "High Flying, Adored" and the Dark Reprise of "Oh What a Circus" (which are both technically laments for Eva, not himself). Peron has "She is a Diamond", which is a lament for Eva. The entire ensemble has the opening song, "Requiem for Evita". "You Must Love Me" was written specifically for the movie, and "Another Suitcase in Another Hall" belongs to another character in the stage version. However, both the movie and stage versions end with the appropriately titled "Lament," in which Eva wonders whether all of her scheming and manipulating were worth the toll it took on her life.
• Le Blues du Businessman from Starmania may count.

Web Original

• The final song in Dr. Horrible's Sing-Along Blog seems to go back and forth between this and a straight Villain Song.
• Edgeworth's song in Turnabout Musical, "Decree of the Prosecutor", has him question his own tactics as a prosecutor. "For if I cheat in the court can I say with a straight face that I'm a better man than the sort that I prosecute every case?".