That’s the one. Tasty, eh?
What about Velvet Underground?
Shiny Shiny Boots of Leather
shiny, shiny, shiny boots of leather
whiplash girlchild in the dark
comes in bells, your servant, don’t forsake him
strike, dear mistress, and cure his heart
…
kiss the boot of shiny, shiny leather
shiny leather in the dark
tongue of thongs, the belt that does await you
strike, dear mistress, and cure his heart
Okay, maybe not so creepy. In fact, I guess it’s kind of sweet…
Roger
Santa Claus Is Coming to Town
“…He sees when you are sleeping
He knows when you’re awake
He knows when you’ve been bad or good
So be good for goodness sake
You better watch out
You better not cry
You better not pout…”
This song freaked me out when I was 9 or 10. I haven’t liked it since, and I have a great distrust of Santa Claus (Satan Claus) to this very day. 
I thought so. Cool song… in a creepy, gross, nasty kind of way. 
Maybe, maybe not. The guy who wrote the lyrics says no. Seems the mule thing got invented later:
http://www.songfacts.com/detail.php?id=2005
http://laststandingman.tripod.com/The%20Buoys/The%20Buoys,%20by%20J.%20Chintala.htm
http://www.rupertholmes.com/interviews/fynsworth_ten_question_QA.html
In that case you’re sure to …er …‘like’ the others on my list. 
Well - we must have had the second “release” of the song because I specifically recall the jacket with a letter on it, stating Timothy was a mule.
marketing department and the censors?
Let’s spend some time together.
-Mick & Keith-
Randy Newmans little ditty about a child murderer has always creeped me out a lot.Weird song.
Slan,
D.
Time for a funny suicide song:
The Water’s So Cold
(by Harlan Howard)
The crest of the waves break over my head
My strength’s almost gone and soon I’ll be dead
I’d rather be dead out here in the sea
Than to love a woman who never loved me
Chorus
Oh the water’s so cold, out here in the dark
The water’s so cold–as cold as your heart
The lights from the shore are fast growing dim
The water’s so cold, I can’t hardly swim
I offered my ring and I offered my name
She said, “You’re a child”; she put me to shame
If she saw me now she’d have to agree
Most men couldn’t swim this far out to sea
Chorus
Yeah, the water’s so cold I can’t hardly swim
How about “The Freshmen” by Verve Pipe?
I’ve always thought that a disturbing little song.
Or,
Marc Cohen’s “Strangers in a Car”
Strangers in a Car
There’s a stranger in a car
Driving down your street
Acts like he knows who you are
Slaps his hand on the empty seat and says
“Are you gonna get in
Or are you gonna stay out?”
Just a stranger in a car
Might be the one they told you about
Well you never were one for cautiousness
You open the door
He gives you a tender kiss
And you can’t even hear them no more —
All the voices of choices
Now only one road remains
And strangers in a car
Two hearts
Two souls
Tonight
Two lanes
You don’t know where you’re goin’
You don’t know what you’re doin’
Hell it might be the highway to heaven
And it might be the road to ruin
But this is a song
For strangers in a car
Baby maybe that’s all
We really are
Strangers in a car
(Driving down your street)
Just strangers in a car
(Driving down your street)
Strangers in a car
There’s a good candidate for rational-emotive therapy if I ever saw one.
“Don’t Fear the Reaper,” (Blue Oyster Cult)… Oh, a footnote – How 'bout those “heavy metal umlauts”? I wasn’t aware of this, not being a metal fan, but BOC always had one over the “O”, evidently…Wikipedia tells me that they, in fact, invented it…and all this time I’d assumed that absurd affectation originated with Mötley Crüe. “Röck döts” and the reasons behind them are silly-creepy.
Maybe I ought to get me some rock dots.
Rëasönablë Përson
Wälden
The traditional blues tune ‘Boot Hill’ covers misogynist-creepy, but the trad songs from an RIP POV like ‘Sam Hall’ just strike me as funny.
Dang! As I began to read that, I was hoping for a one of the classic Waldco™ product line announcements. Like, maybe, Wäldcö™ Rock Dots.
A lot of good nominees here. I’ll have to agree about Mack The Knife, Last Kiss.
This one’s not “pop” but Mac Wiseman did one about a little girl who’s mother has disappeared and she goes out to find her daddy who’s at the “store with the bottles on the wall”. When she gets there he flys into a demented, drunken rage and hits her with a chair and she dies horribly.
That song really disturbs me.
“Possum Kingdom” by the Toadies is about Vampirism.
The Police’s “Every Breath you Take” isn’t the only song sung from a stalker’s perspective…
http://www.popculturemadness.com/Music/Stalker.html
Jewel has a pretty good stalker song on her otherwise awful 0304 CD, I believe it’s called “Haunted”
Bare Naked Ladies have some seriously creepy stuff… “Straw Hat and Old Dirty Hank”,
“Wrap Your Arms Around Me”, and “The Flag” come to mind.
I’m surprised no one has mentioned Blinded By The Light yet …
“Blinded by the light, wrapped up like a 
another in the night…”
I know it really doesn’t say that, but for years i thought it did! 
What about Sex and Candy by Marcy Playground?
while it may not actually fit the description…
“Muskrat Love” really disturbs me!!!