Which reminds me, how about “In the Air Tonight” by Phil Collins (especially with the urban legend associated with the song)?
“Rambling Man” by Hank Williams (Sr.) – it starts out as an apology for being a wanderer, and ends as basically a suicide note:
And when I’m gone, and at my grave you stand
Just say God’s called home, your ramblin’ man
Mississippi bluesman Skip James (1902-1969) recorded lots of creepy stuff. In “Cypress Grove Blues” he longingly wishes death on his faithless woman:
When your knee bone’s aching and your body’s cold
You’re just getting ready, ready for the cypress grove
Thought of another … Monster Magnet’s See You In Hell.
A guy and a girl have a fling. She gives birth in a motel room. She kills the baby and has him bury it in a Jersey landfill.
If that weren’t bad enough, the baby comes back to life as undead and hunts them down.
The song is played with a 60’s Munsters style keyboard.
Almost everything by Greg Dulli, formerly of the Afghan Whigs and now a member of the Twilight Singers. His songs are intensely sexual and he always sounds like he’s one step away from doing something perversely violent.
The last half of “1965” sounds like it was meant to be the perfect soundtrack for anonymous, dirty, back-alley sex.
Although people now often associate him with soundtracks to Disney movies, many of Randy Newman’s songs from the first part of his career were deceptively sinister. Case in point: “Sail Away.” The Copland-like melody of the song hides the fact that it’s about a slave-trader trying to trick an African child into bondage by telling him about a wonderful land America is.
Mack The Knife has always had nasty lyrics (he’s a serial killer) but it wasn’t until Jimmie Dale Gilmore’s version that the music matched the words in “sinisterness”. For some bizarre reason it had always been sung as an up-tempo, fun song 
.
“Grimly Fiendish” by **The Damned ** has a theatrical, music-hall, playfully sinister quality, as opposed to the psychologically disturbed, serious sort of sinister. “Dead Man’s Party” by Oingo Boingo is more cartoonish still, although the lyrics at face value are ghoulish.
“Two-Dollar Wine” by **The Glands ** has that sinister vibrato-thing going on in the guitar strumming. Off the album Double Thriller, with B-horror-movie-like artwork.
**Robyn Hitchcock ** (ex-Soft Boys, solo artist, and again with the Soft Boys) has an ongoing obsession with the morbid and perverse, not all of it sinister-sounding (“My Wife and My Dead Wife”). To me, though, he sounds his eeriest when he seems to be channelling John Lennon (“Ted, Woody and Junior”).
Much of Talking Heads’ Fear of Music.
A lot of Barry Adamson’s stuff. Ditto for Siouxsie Sioux and the Banshees, mining that art/Goth-lite vein… And David Tibet, whose alienated soundscapes/chanting mixes go beyond Goth and into the satanic, or maybe alien.
But my all-time Most Sinister Album would have to be the soundtrack to The Wicker Man, with its blend of traditional and original songs and instrumentals. It helps to have seen the movie, of course, but I think one would find much of the music sinister-sounding anyway (those Lydian arpeggios!).
Speaking of Jimmy Dale Gilmore, how about Where You Going? The song is part obsession, part psychedelia, part psychosis, and all to a beat that might leave Johnny Cash feeling a little unsettled.
That’s just the way Brecht and Weill worked, I think.
But my all-time Most Sinister Album would have to be the soundtrack to The Wicker Man, with its blend of traditional and original songs and instrumentals. It helps to have seen the movie, of course, but I think one would find much of the music sinister-sounding anyway (those Lydian arpeggios!).
[/QUOTE]
There’s lots of sinister in folk and folk-rock:
Mr Fox - Mendle, Mr Fox, Rip Van Winkle - hell, virtually their entire output!
Fairport Convention - Admiral Gower, Crazy Man Michael, Bring 'em Down, Sloth…
Waterson/Carthy - The Holland Handkerchief
Oysterband - We Could Leave Right Now, Road to Santiago.
Can’t believe I’ve unlurked just for that! Just call me folk geek. (Hiya y’all, by the way!)
Another (mostly) lurker checking in. Usually someone mentions my songs before I can chime in.
Can’t believe no-one has mentioned **Ghost Town ** by The Specials
and a lesser known All Roads Lead to Rome by the Stranglers
I love that someone else knows who Snakefarm is! I’ve been an Anna Domino fan since about 1988. She has such an amazing, husky voice.
Siouxsie & the Banshees do sinister very very well. I especially like their cover of “Trust In Me.”
Kate Bush’s “Get Out Of My House” and “Leave It Open” are creepy, as are “Pull Out The Pin” and “Waking the Witch.”
Toyah’s “The Creepy Room” fits the bill.
Since I can share these with her full permission, I’m going to. Forget her name, it’s her real name, and it has no bearing on her music, much of which is very dark. Happy Rhodes does creepy wonderfull well.
Picking from early songs (at the time, she was an apprentice engineer at a recording studio, and recorded her own songs to learn the equipment, never realizing at the time they’d one day be gathered together and released on albums. Everything you hear is her), here are several:
Beat It Out (a slo-mo nightmare, this was an exercise in seeing how low she could get her voice to go)
I’m Going Back (“Where are my monsters, and cats? Where are my attic antiques, and bats?”)
Take Me With You (a creepy waltz about murder-suicide)
Possessed (about insanity)
Asylum Master (see above)
Project 499 (see above)
From her middle period, when she decided to make “real” albums…
To Live In Your World (creepy song from the point of view of a murderer)
Lay Me Down (imagine blood-red roses strewn on black velvet)
Cohabitants (that little creature who’s trying to drive you insane is back)
From more recent work…
Winter (simply haunting)
If Wishes Were Horses How Beggars Would Ride (a great regret, and great sadness)
She has several other pretty and/or jaunty songs about death and depression and monsters and vampires and sucide, and the music makes them, to me, even creepier. I’ve only scratched the surface. Believe it or not, she’s a very funny person and has a great sense of humor, she’s not all morose or anything.
(If I could share mp3s of Siouxsie and Kate and Snakefarm and Nick Cave and Toyah too, I would.)
The soundtrack to Twin Peaks is my number one creepy album.
Sometime ago I heard a cd from a Finnish group called “His Infernal Majesty”; it had their version of Don’t Fear the Reaper which still sticks with me.
But the one I listen to every Halloween is the Pogue’s Turkish Song of the Damned.
A while back Glenn Danzig did Black Aria, an orchestral, instrumental album, that qualifies as sinister. Each song is only a few minutes long, and the entire disc is only about 30 minutes, but it is very dark and moody. Good stuff.
More than a few songs by Marilyn Manson are pretty sinister. The first time I had a friend listen to Portrait of an American Family, the intro, Prelude (Family Trip), where Marilyn recites the famous tunnel “speech” from Willy Wonka, creeped him out so much he refused to listen to the rest of the album.
Their version of I Put a Spell On You is pretty creepy too, but more due to the lyrics than the music.
Regarding the Toadies song Possum Kingdom, I don’t think there is any more argument for one interpretation over the other, and personally prefer the more fanciful one.
“Suddenly Last Summer”–The Motels
“Synchronicity II”–The Police
But what a great jam! And let’s add “Gimme Shelter” to the list as well. The Stones were rather good at this sort of thing back in the day.
But what a great jam! And let’s add “Gimme Shelter” to the list as well. The Stones were rather good at this sort of thing back in the day.
Screamin’ Jay Hawkins’ iconic version of that song is pretty damn sinister itself. It’s downright SCARY.
Also, anything by Paul McCartney, Jimi Hendrix, Kurt Cobain, Elliot Easton (Cars), Tony Iommi (Black Sabbath), Greg Lake, and many others.
Because they play left-handed. Sinister, get it?
D&R.
I took my username from that one (I had bought that single one day when I made my first MUD character who got to be Coil)
To have and to hold? Really? In what way?
Can’t comment on the new one until I buy the album on Monday.
I’ll add another vote for Mr Cave and toss in Leather Strip’s version of Venus in Furs.