Laibach: "The Lonely Goatherd"
At once the most innocent and the creepiest song on this list, by the masters of subversion. 2:25 makes me weep with amusement. Sorry Mom, but The Sound of Music had it coming. Insufficiently disturbed and want more? There's an entire album, which I guess we can thank North Korea for: "So Long, Farewell"; "The Hills Are Alive"; "My Favorite Things". https://www.youtube.com/watch?v=5jqOSDq0Ssc
Human League: "Circus of Death"
The original synthpop band. How did they move all the way from the pioneering brilliance of "Being Boiled" to the sugary pop of "Don't You Want Me Baby"? And how is it that I can love both? "Circus of Death" is my favorite, because how can I not love a song about a creepy clown conquering the world with drugs? Or is it a prophecy of coronavirus? Spare me and my family! https://www.youtube.com/watch?v=EExTxmQKPi0
Rose McDowall: "Cut with the Cake Knife"
McDowall was the goth pixie who covered Dolly Parton and is usually remembered as the one-hit wonder, Strawberry Switchblade. She's like Siouxsie Sioux's cuter, funner, younger sister, but still creepy, underneath that shiny candy shell. https://www.youtube.com/watch?v=u8K1UDOr9TY
The Police: "Mother"
The members of The Police were a little bit older than members most of the punk and new wave bands of that era, but in some deep B-sides they still showed a delightfully juvenile fascination for the morbid. "Friends", an ode to cannibalism, is a good example, as is the better known and far more substantial "Once Upon a Daydream". The psychological pastiche of "Mother" is ripe fodder for freshman English papers. https://www.youtube.com/watch?v=d56MfuZAfwI
Bonus 6th: Erica Nockalls: "Goodbye Spider"
Can a breakup song be creepy without being threatening? I guess if it's about host bodies and sung to a spider. "I still feel your breath on the backs of my eyes." *shudder* https://www.youtube.com/watch?v=jlExxL-0SzU