I thought I’d start a thread for creepy pop songs. Pop songs, for these purposes, will be defined as any commercially recorded and released secular, non-classical, songs.
I nominate,
Heaven’s Just A Sin Away, sung by father-daughter country & western duo, The Kendalls.
He Hit Me (It Felt Like a Kiss), sung by 1960’s “girl band” The Crystals.
Good nominees, Walden. Most of the songs I can think of are dumb but not necessarily creepy.
I think Having My Baby by Paul Anka comes close though.
Strange Fruit and Gloomy Sunday.
Steppenwolf’s The Pusher
Past close for me! 
…although I can see where a case could be made for extremely sappy…
Ode to Billy Joe seems sort of creepy to me.
Oh, it is. The difference…perhaps…is that I think it’s meant to be.
Yes, I think it is meant to be too.
I think I’m having a problem here Denny commented on in another thread. I can see now that the others are creepy for reasons the writer did not intend. Stop laughing, Denny. Is this irony? If it is, that’s why I can’t do it.
Ack!!! Lyle is Lyle and Roy is Roy! Lyle has, at least his share of, creepy lyrics but If I Had A Boat is not one of them. Ack!!!
Alice Cooper…Dead Babies
-or- just Alice in general! 
I missed the Stop laughing
Sorry,
Surely Walkng on Sunshine by Katrina and the Waves has to be a candidate. Also Lean on Me by Bill Withers. These are both so icky sweet that you just know there must be a malevolent spirit force driving them forward.
djm
That song is called If I Had a Boat? How odd.
Okay, I think we have ironic and we have unintentionally creepy, two categories which do not overlap. I can think of no songs for either category. I am, however, looking forward to seeing other people’s creepy songs. Ack!!!
My all time pick for creepy is Yummy Yummy Yummy (I’ve got love in my tummy)… by The Archies…I think?
Ma Belle Ami by some furrin’ group (was it Dutch or Svenskas?)… Just a weird song.
Seasons in the Sun by Terry Jax, because it seems like it might provide that little extra push that a homicidal maniac needed.
While I believe this started life as a poem by Lewis Allan, rather than popular song, its famous recording by Billie Holiday is indeed disturbing, especially for those of us in regions where it was all too true (which is much more of the United States than is often mentioned).
I’m glad I’m not the only one who feels that way about the Kendalls. I’d swear I’ve also seen them do Voulez Vous Coucher Avec Mois? on TV, though they don’t seem to have recorded it. It’s not the songs that are creepy to me, but the performances–knowing their relationship.
The story line of Janie’s Got a Gun is more than a tad creepy.
So is Suzanne Vega’s Luka.
I find most murder ballads basically creepy. There aren’t that many that qualify as “pop”, though. Maybe Hey Joe?
Ohio Express, I think. Still, pretty creepy. Right up there with 123 Red Light by The 1910 Fruit Gum Company. And what about Andy Kim?
Sinead O’Conner seems pretty creepy to me all round.
djm
“Lola” is my pick.
“Private Eyes” is Shan’s.
–James
Heh heh… yeah.
I couldn’t decide among Madonna’s songs.
Babes in the Woods, The Cruel Mother, and Banks of the Ohio qualify as creepy. Perhaps Tom Dooley crossed over from the creepy ballad “genre” to pop song.
Man, I’d forgotten that one. Good choice! L-o-l-a- Lola 
djm