For some reason, “For the Longest Time,” by Billy Joel kind of freaked me out as a wee lad.
Not a song, per se, but the theme from the TV show Unsolved Mysteries scared the shit out me – mostly if I had fallen asleep with the TV on and the lights out and it was playing when I woke up.
I’ve seriously turned on all the lights and checked under beds and behind doors because of this one.
But I think they meant to do that.
One night back in the 80’s I was driving to St Louis in the middle of the night and one of the St Louis radio stations was playing Triumvirat’s “March To The Eternal City” (from the “Spartacus” LP). I never really thought of that cut as being that creepy, but driving down the highway alone in the middle of the night… yeah that kind of freaked me out.
Ricky Valance’s Tell Laura I Love Her distressed the hell out of me when I was a juvenile. (It still does, just not the same way.)
It’s just a maudlin little teenage death song of the sort that was so popular at the time, for some reason it was MORTALITY writ large to me. It sounds as creepy as hell, too. If Dean Stockwell sang Tell Laura I Loved Her in Blue Velvet instead of In Dreams, I would have absolutely pissed my pants, instead of just choking in fear a little.
Uncle Albert by… Paul McCartney? Wings? Whatever. I still hate it today. It used to make me think of Aunt Bird from Mr. Dressup, and that bird skull head from the Eagles Greatest Hits album cover. Don’t ask.
Anything with violins in it, or synth violins, or something. There were a couple of songs on the radio around that time, around 79-81ish, that had these creepy, sad-sounding violin-y sounds that would freak me right out.
Sailing by Christopher Cross used to make me howl in sadness, because there was a television show with a cat on a surfboard they showed surfing around, using that song in the background, and I always wondered how the damn cat could get back home - since cats hated water. I loathed that song.
Another vote for Nights in White Satin.
The theme song for “The Littlest Hobo”.
Dead Puppies depressed me, and I would always leave the room.
Anyone own the album Sandinista! by the Clash? You know those little parts in between songs they threw in there? “Have you ever asked yourself: Who holds the key that winds up Big Ben?” before Silcone on Sapphire, or that one before *The Call Up * (was it before The Call Up? Or am I getting it backwards?)where the same guy starts that spooky-ass singing? Holy crap, did that ever scare the bejiminies out of me! I also wasn’t terribly fond of the kid singing The Guns of Brixton.
Brr.
Black Sabbath. Devil music.
Bohemian Rhapsody. *Especially the video - four floating multipying heads! *
A group called Bloodrock did a song titled DOA. The song started out with a very realistic siren sound–one that made me check the rearview mirror every damn time it came on the radio.
Here’s a link to the lyrics and a little sample:
“Life is flowing out my body.
Pain is flowing out with my blood.
The sheets are red and moist where I’m lying.
God in Heaven, teach me how to die.”
Now, is that uplifting or what?
Revolution No. 9 kind of creeped me out when I first heard it. Then it just got annoying.
As a kid sharing a room, my older brothers would play music to help them fall asleep. While the were playing the entire side of Rush’s “2112” and falling blissfully asleep, I was wide awake and wondering if the noise I heard were the priests from the Temples of Syrinx. Some of the Beatle’s psychodelic sounding stuff used to not exactly lead to peaceful slumber.
Didn’t scare me, and it wasn’t on the radio, but the video for Michael Jackson’s “Thriller” seriously freaked out my nephew when it was in heavy rotation. Understandable, since he was only about three years old at the time and the King of Pop’s transformation into a cat-monster was very unsettling.
“Horse with No Name” (Neil Young) STILL freaks me out, frankly. But when I was kid, I’d get frantic if I had to listen to it.
Oh, and “Alone Again (Naturally)” - SO depressing! 
Ugh, right you are, I always get it mixed up with “Heart of Gold” for some reason. Which also creeps me out, but not as bad. I’m glad I didn’t attempt an artist on the other song!
The zombies freaked me out (I was probably about 9 at the time). Especially the one that opens his mouth and it’s full of blood.
I remember waking up one summer morning to the clock radio playing “What if God Was One of Us?” and being seriously spooked by the melody.
I think falling asleep or waking up to a song enhances the potential creepiness of it.
Another vote for DOA by Bloodrock.
(For years I thought it was Knights in White Satin. I presumed it was about people with gender issues.)
What a great question-
Stairway to Heaven
I would listen to radio falling while falling asleep and that song scared me to death.
I’m still not thrilled when it comes on the radio…
Absolutely, that one.
That was out around 1970. I was nine years old then. That summer, I saw a horrible accident near my house (that probably ended up in fatalities, but I never found out. We saw it by driving by, and my Mom kept us out and away from home for several hours.) My older sister also died that Halloween (from cancer.)
That song could send me into depression or near hysterics when I heard it.
In the mid-70s, there was a song with (I think) the title “Love Rollercoaster,” and there was a story going around our school that someone had been murdered in the studio while this song was being recorded; if you listened really closely, you could hear the murder victim screaming in the background. So, whenever it was on the radio, we listened really closely… and while I never heard anything definite, that song always creeped me out just by association.
I was in trouble and dreading retribution, and the big hit of the day was Gerry Rafferty’s Baker Street. For some reason, that wailing sax just cranked up my anxiety.
Psst…your other song (“Alone Again (Naturally)”) was Gilbert O’Sullivan. 