Your happiest sounding song with the saddest lyrics...

The original lyrics of “Greensleeves” are about a man falling in love with a prostitute, and how he longs to be with her but can’t have her.

“Alas, my love, you do me wrong
To cast me out discourteously.
For I have loved thee for so long,
Delighting in thy company.”

My mother always told me that Irish prostitutes made themsleves known by their green sleeves, but I can’t back that up.

As for “Have Yourself a Merry Little Christmas,” I read recently that it was originally from a movie about a midwestern family whose father gets transferred to the big city right around Christmas time. Either they will all have to leave the life and the town they love, or he will have to go alone and break up the family. Either way it sucks. So the song is originally sad. I could have sworn I read that in a Straight Dope staff report, but I couldn’t find it when I did a search.

Speaking of Christmas songs, “The Angel Gabriel” and “God Rest Ye, Merry Gentlemen” always sound spooky and ghostly to me.

My nomination would be “Allison” by Elvis Costello…a tale of murder masquerading as a love song. Although I guess it’s an overused example.

Well well Mr. Evil. You have truely lived up to your name bringing up this song.

I curse you.
CURSE YOU SCOTT EVIL!!! CURSE YOOOOOUUUUUUU!!!

“Have Yourself a Merry Little Christmas” was written for the movie “Meet Me in St. Louis,” in 1944.

The movie’s kind of an alegory of the time: The guy leaving home is going off to war; the small town left behind is the simplier pre-war life, and so forth.

It’s my understanding the song was supposed to be a bit bitter-sweet, like, “Let’s think of the good times we’ve had and the better times to come after this damn war is over, and we’ll all be together again (if the fates allow, of course).”

It’s a good song for those of us who like to avoid the rush and start our ‘post’-holiday blues early.

“A Man of Great Promise” - Style Council

Happy as could be about a guy who kills himself.

Oops. Anyway, you get the idea. :o

the Bangles version of Hazy Shade of Winter

You’re all wrong. It’s Pink Floyd’s “Free Four”, with such uplifting lyrics as:

“The memories of a man in his old age, are the deeds of the man in his prime…
You shuffle in the gloom of your sick room, and talk to yourself as you die…”

All to this upbeat, mid-tempo roustabout…Timmy

wow, you’re right tim, i totally forgot free four, thats the best so far

The Titanic song. As far as I know, it’s never been done by any artist; it’s more of a camp song. It goes something like: They built the ship Titanic, to sail the ocean blue/and they said it was one ship, the water would never go through/but the Lord’s almighty hand, knew that ship would never land/It was sad when that great ship went down. And so on, for four or five more verses, all done in a cheerful, happy sort of tone. Very odd.

Also, Tom Leher’s So Long, Mom: A Song for World War III. Armmageddon to upbeat piano music.

“It’s A Mistake” by Men At Work, another catchy little song about nuclear apocalypse.

Um, it has to be “Big Yellow Taxi” by Joni Mitchell.

“Kivutar” by Värttinä. It’s an upbeat folky little song. The lyrics translate as:
“The Goddess of Pain has a kettle, the Daughter of Evil has a pot: and in it she’s cooking up a mess of pain” … “Up on Misery Ridge roams a pack of suffering hounds, dogs the colour of frost, howling in pain on the hill, suffering and whimpering”

I’d have to go for Karma Hotel by the Spooks

Quite an upbeat tempo and female singer has a beautiful, soothing voice but the lyrics are actually really morbid (russion roulette amongst other things)

http://www.azlyrics.com/lyrics/spooks/karmahotel.html

Hmm, well perhaps it becomes a bit subjective here. I guess I’d go so far as to say that the singer is trying to get over things.
While it’s good that the he’s decided that ‘there is too much to do before’ he dies, I am not sure that the tone of ‘got to stop believin’ in all your lies’ matches the cheery uptempo melody.

Uh Just like Heaven isn’t a depressing song…it’s about hyperventilating while kissing, as far as I knew.

‘You keep me Hangin’ On’ would get my vote…or ‘Mandy’ by Barry Manilow or possibly ‘I Never Thought You’d Be a Junkie (Because Heroin is so Passe)’ (about the lead singer’s ex getting into heroin).

Since we’re into apocalypse songs now, how’s about Ultravox’s Dancing with tears in my eyes?

You’re right, but you neglected to mention the best of the lot – “Narrow Your Eyes,” the tale of a man who won’t get off the bus and go home to his girl because she’ll be mad.

“They’ll Need a Crane” can be heartbreaking, too – *
They’ll need a crane, they’ll need a crane
To take the house he built for her apart
To make it break, it’s gonna take
A metal ball hung from a chain.*

And their very first single, “Don’t Let’s Start” is another wildly peppy song about bad love.

“Conquistador” by Procal Harum, live with the Edmondton Symphony Orchestra – possibly the greatest live recording ever.

Conquistador*, your stallion stands
In need of company.
And like some angel’s haloed brow,
you reek of purity.

It’s basically a song lamenting the corpse of a Spanish soldier, lying on the beach as the surf washes over him.

“I know you came with sword held high
You did not conquer, only die.”

Still, a fantastic piece. Definitely crank-it-up-to-11 worthy.

“Conquistador” by Procal Harum, live with the Edmondton Symphony Orchestra – possibly the greatest live recording ever.

Conquistador*, your stallion stands
In need of company.
And like some angel’s haloed brow,
you reek of purity.

It’s basically a song lamenting the corpse of a Spanish soldier, lying on the beach as the surf washes over him.

“I know you came with sword held high
You did not conquer, only die.”

Still, a fantastic piece. Definitely crank-it-up-to-11 worthy.

(*And by the way, it’s pronounced “con-KWIST-a-dor,” not “con-KEE-sta-dor.” How cool is that?)

The Housemartins had some very catchy depressing songs, none of which spring to mind at the moment.