There’s loads of that sort of stuff in traditional folk - severed heads, hearts in goblets of wine, serial killers (“it’s six king’s daughters here have I drowned/ And you the seventh will be”). Very jolly… 
Neil Young’s “Down by the River” comes to mind.
And Boomtown Rats’ “I Don’t Like Mondays” as well.
But it’s such a wonderfully over the top song to sing along to (and “One Night Only” which is still just as screwed up from a relationship angle but at least has slightly healthier self esteem.)
But then, musicals are not a good place to look for psychologically well characters.
Ack. A better cite is Harry Nilsson’s version. It is much more anguished, and didn’t he write it? Anyway, it is likely tongue in cheek, if you consider his song “You’re Breaking My Heart” (“you’re tearing it apart, so fuck you”) off of Son of Schmilsson.
I didn’t see mention yet of Dido’s White Flag
Once I really listened to the lyrics, that song began to practically make me angry thinking “the last thing I’d want would be some clingy chick who screwed up our previous relationship and now can’t get the hell on with her life and let me live mine”.
Oh, I agree. The next time it comes on the radio, instead of singing along, just starting screaming at regular intervals: “How did you get in my room?” “Help, police!” “I don’t know you, lady!” "Oh, God she’s gonna kill me!"and generally whimper and plead for your life.
Since Jim Steinman loves to write songs with punny titles, Meat Loaf’s “Left in the Dark”; later he’ll find out who she’s been fucking, but for now, turn out the lights and “leave him in the dark” while he has sex with her anyway:
I bet you still got a trace of his love in your eyes
And you still got his eyes in your mind
You swore you’d be with me at 7 o’clock
Now it’s a quarter to 3
Well whatever you got and whoever it was
I guess you couldn’t get it from me
No I guess you couldn’t get it from me
But down in my soul - down in my soul
I know - I know that you love me
There’s no need to talk
I see the look in your eyes an’ I got the proof
And there are no lies on your body
So take off your dress
I just want to get at the truth
Okay, I heard this song YEARS ago and worked it into some writing I was doing at the time, but I have no idea what in the world the ACTUAL SONG is! Care to give a fellow doper a hint?
Lady Isobel and the Elf Knight?
Reminds me of the Sting song “Love is Stronger than Justice (The Munificent Seven)”
The town mayor was happy but his face was glum
The maidens numbered only one
But there weren’t seven brides for seven brothers
I knew I had to get rid of the others
…
Mother told me I was the clever one
The seventh son of a seventh son
It all ended so happily
I settled down with the family
I look forward to a better day
But ethical stuff never got in my way
And though there used to be brothers seven
The other six are singing in heaven
from Carousel:
“Common sense may tell you
That the ending will be sad,
And now’s the time to break and run away.
But what’s the use of wond’ring
If the ending will be sad?
He’s your feller and you love him,
There’s nothing more to say.”
Correct (Though I was thinking of Steeleye Span’s version which is slightly different - no parrot for a start).
Snopes is on the fence about this. I admit I haven’t heard it myself.
You know, I’ve sung that song before, and it’s not psychologically unhealthy, it’s frustrating–the meter is off and it never works with the notes.
For a disturbing folk-song, though, I’ll submit one of Loreena McKennit’s favourites: The Bonny Swans.
Iron Man by Black Sabbath is rather dark, and the cover by The Cardigans is mindbending:
And this one by Tift Merritt evokes death…
Google knows psychologically unhealthy, all the ads are for Celine Dion
I don’t think this one really counts for the OP Leaffan. He’s looking for songs that are supposed to be romantic but are actually creepy. Jimi Hendrix’s “Hey Joe” was intended to be a messed up song about a guy making a horrible mistake and trying to avoid the consequences. Not only is it in no way presented as a romantic song, but Joe kind of gets what’s coming to him in the end (depending on how you look at things).
Wow, on review, a lot of you guys, especially in the 2nd page, are missing the point of the thread. It’s not about songs that are merely dark or disturbing, or Ozzie Osbourne’s “Diary of a Madman” would probably win the thread; that or Eminem’s song about the obsessed fan that commits suicide by driving off a bridge with his pregnant girlfriend tied up in the trunk.
The point of the thread, according to the OP, was for songs whose intent, or at least the commonly understood intent, is to be romantic, but which portray a disturbing outlook.
Man was this thread hijacked 
I knew I liked you for a reason. Jim Steinman’s got a bunch of songs about disfunctional relationships. There’s I’ll Kill You If You Don’t Come Back the title of which should speak for itself and I’m Gonna Love Her for Both Of Us in which a man tells his best friend he’s mistreating his girlfriend so the singer’s going to steal her away. I think I’d Lie For You (And That’s the Truth) got some airplay a while ago in which the singers say that, unlike a previous hit, they really would do anything for love. My favorite Steinman disfunctional relationship song is More Than You Deserve. The first time the chorus comes around, Meatloaf sings,
The song progresses until you get to the last chorus which is so over the top it makes me laugh. I’ll spoiler it to be on the safe side:
[spoiler]Then I saw you making love to two of my best friends
I didn’t know whatever to say
I saw you making love to a group of my best friends
So I looked them right in their eyes and I said
Listen here, group
Won’t you take some more, it’s what you came for
…
Won’t you take some more boys, it’s more than you deserve[/spoiler]
If anyone’s interested, the full lyrics are here, including a reference to a truck stop. I can just picture what would happen if this guy came to the SDMB asking for relationship advice!
Yes!! LISTEN HERE, GROOOOOP!!
Almost as funny as:
Somebody bless all the cheerleaders down on the tracks
They’re glistening like diamonds with sweat on their backs
from I’ll Kill You If You Don’t Come Back
Man I love me some Jim Steinman!!