I found all the songs on YouTube, so I linked to those. There is some adult language in some of these, so be aware of that (I know #12-14 for sure, and probably #17, but I can't remember).
1. "Come Look At the Freaks" from Side Show. As you can probably guess from the title, this musical is about a group of people working as side show freaks. The song emphasizes how drawn we are as humans to the scary, the "unnatural," and the unusual. There's always just a hint of the suggestion that we are the freaks for being so fascinated by the macabre. I figured this was an appropriate opening for the mix!
Come look at the freaks
They'll haunt you for weeks
Come explore why they fascinate you
And flush your cheeks!
2. "Hold Me, Bat Boy" from Bat Boy. I discussed Bat Boy on this blog about a month ago and covered most of it there, so let me copy over some of what I said there: "This song talks about the Bat Boy found in a cave and all the ways he was mistreated. It even nicely provides us with a moral." It's one of the darker songs from the show.
In a cave many miles to the south
Lives a boy born with fangs in his mouth.
Sleeping until the fading light,
Flying through bloody dreams;
When he awakes the summer night is filled with screams.
3. "Sunset Boulevard" from Sunset Boulevard. This has always felt to me like a haunted house song, even though this character is not physically trapped here - just psychologically. He realizes what is happening to him but finds himself unable to escape from it.
Sunset Boulevard, twisting boulevard
Secretive and rich, a little scary
Sunset Boulevard, tempting boulevard
Waiting there to swallow the unwary
4. "Cell Block Tango" from Chicago. This is, IMHO, one of the best villain songs to ever appear in a musical. Each murderer tells their story with not only a complete lack of remorse, but also a sense of wicked glee at what they've done to their men. It's very creepy, but extremely entertaining.
So that night, when he came home, I fixed him his drink as usual... You know, some guys just can't hold their arsenic.
5. "The Master's Song" from Dracula. Truth be told, I don't know this show very well and just discovered this one today as I realized I had the studio cast of Dracula and couldn't not include something from it in this mix. It's sung by Renfield, a servant and worshiper of Count Dracula. It's a great creepy little song and I definitely am going to be listening to this one more often now that I've discovered it.
Master! They think a locked door prevents you
You're on your way, I can sense you
Through the window, through the grating,
Through the floorboards, through the fanlight
Comes the mist
And your kiss!
6. "Malevolent Oberon Suite" from A Little Midsummer's Night Music. This is Groovelily's musical adaptation of A Midsummer Night's Dream and this really isn't that scary a song lyrically - Oberon, the fairy King, is plotting revenge on his wife, and the lyrics are taken directly from the play - but the music creeps me the heck out. "Malevolent" is absolutely right.
And with the juice of this I'll streak her eyes,
And make her full of hateful fantasies.
7. "The World Has Gone Insane" from Jekyll & Hyde. Frank Wildhorn sure knows how to write dark music. I ended up choosing this one over "Alive" from the same show because although "Alive" is a great villain song, this one is sung by Jekyll about how he knows he is completely losing control, and to me that is a much creepier theme.
The world has gone berserk
And hiding in the murk, new monsters lurk
I see a sea of snakes upon the floor
I see the reaper grinning at my door
8. "Sweet Transvestite" from The Rocky Horror Show. (Or The Rocky Horror Picture Show, depending on the version you're referring to. Either way, it's another show that had to be included in this mix.) This is a slightly lighter song than the past few, but amidst all its campy entertainment there's definitely a sense of "Yeah, those main people are going to end up dead." Don't trust anyone living in a big creepy castle with a bunch of mysterious servants.
So you got caught with a flat, well, how about that?
Well babies, don't you panic.
By the light of the night when it all seems alright
I'll get you a satanic mechanic.
9. "The Phantom of the Opera" from The Phantom of the Opera. Although I debated a few other songs from the show, this one ultimately is the showtune monster anthem. It's pretty much instantly recognizable as such. And no matter how many times I see the show or how much I recognize that it's kind of silly, I still get a bit of a chill every time I see the dressing room fade away to reveal the Phantom's lair as he lures her down there. Here's to buying the DVD version of the 25th anniversary recording when it comes out so I can watch it without having to suffer through Gerard Butler.
Sing once again with me
Our strange duet
My power over you grows stronger yet
And though you turn from me to glance behind
The Phantom of the Opera is there
Inside your mind
10. "Life, Life" from Young Frankenstein. The Frankenstein story also has to be represented here. Although I do have a song from Frankenstein: The Rock Opera, it's a pretty mellow one that isn't very Halloween-ish... so here's this wonderful mad scientist song for you all instead.
Life, life, ere the break of dawn
Life, life, let my dream be born
Fate, fate, through this storm and strife
Fate, fate, give my creature life
Give my creaure life
11. "It's Alive" from Zombie Prom. And here's a song about a creature who did come back from the dead... Although not because a mad scientist brought him back to life. Nope, Jonny came back from the dead to ask his girlfriend to go to prom with him, much to the surprise of his teachers and classmates.
Lord, would you look at this creature feature
What a disgusting display
Check out this nightmare that rose with the moon
Straight from the depths of the black lagoon
Cover your popcorn and duck!
Frankenstein's running amok!
12. "Spooky Mormon Hell Dream" from The Book of Mormon. Just a warning to my religious friends (Mormon or not), you might wanna skip this one. This show in general has a tendency to offend. I'm a Christian and do believe Hell exists, but I'm also thoroughly amused by this song because I've occasionally had these dreams... although with less Jeffrey Dahmer in them, and usually less prompted by guilt.
Spooky Mormon Hell dream!
Genghis Khan, Jeffrey Dahmer, Hitler, Johnnie Cochran
The spirits all surround you!
Spooky, spooky, spoooo-ky!
13. "Another National Anthem" from Assassins. Maybe kind of a weird choice (I debated "Unworthy of Your Love" instead), but there's something really creepy about a bunch of assassins (many of them probably mentally unhinged) sitting around realizing that their impossible goals weren't met by killing anyone... and then just deciding they need to keep trying and cheering each other on. MEEP.
You've got to try again!
Like they say,
You've go to keep on trying
Until you get a prize
Until you get a prize...
Mustn't get discouraged
Spread the word
14. "Evil" from The Witches of Eastwick. For being a musical all about witches, it's surprisingly light on songs about anything Halloween-like. This is the closest I found. It kind of is a nice song with a theme of "Something BAD is going on and no one will listen to me! Even though I'm vomiting up candles and you would think someone would notice that is not normal!"
Evil, Clyde! And it feeds by degree on our apathy
Evil, Clyde! Creeping in without sound, it starts in our homes,
In our beds, on our floors strewn with clothes.
Like a plague, how it spreads- and pity the woman who knows
15. "Epiphany" from Sweeney Todd. The wonderful (and terrifying) scene where Sweeney Todd goes completely insane with vengeance and fury and decides he's just going to kill everybody. And although I quoted the most obviously evil crazy lyrics down below there, my favorite part is actually when he sings, "I'm alive at last and I'm full of joy!" at the very end. Creeeeepy.
Now we all deserve to die
Even you, Mrs. Lovett, even I
Because the lives of the wicked should be made brief
For the rest of us death will be a relief
We all deserve to die.
16. "Suppertime" from Little Shop of Horrors. Although "Feed Me" would perhaps be the more obvious choice from this show, this one has a darker vibe. Seymour knows exactly what Audrey II is asking of him and deliberately makes the choice to kill off his boss to save himself.
He's got your number now
He knows just what you've done
You've got no place to hide,
You've got nowhere to run
He knows your life of crime
I think it's suppertime
17. "It's Time" from The Evil Dead: The Musical. Let's end on an upbeat note... everyone needs a good zombie demon-fighting anthem, right? Well, this is a pretty great one.
You know that I’m right
I’m not dying tonight
It’s a holiday
When I’m in despair
I adjust my hair
And make evil pay
And thus we conclude my Halloween showtunes mix. I was actually surprised at how many I had in there - I had to do a lot of paring down the list. I ultimately decided to just allow songs from theatrical productions in here, rather than movie/TV musicals. This eliminated the following songs, in case you want even more of my favorite songs about monsters, killers, and demons:
"Friends on the Other Side" from The Princess and the Frog
"Oogie Boogie's Song" from The Nightmare Before Christmas
"Playing With the Big Boys" from The Prince of Egypt
"Slipping" from Dr. Horrible's Sing-Along Blog
"Walk Through the Fire" from Buffy the Vampire Slayer: Once More With Feeling