Enter Sandman?

I'm looking for something less aggressive.

"Empty Box" by Morphine. (Or "The Other Side"?)
"In the Darkest Place" by Elvis Costello and Burt Bacharach.

archagon, if you'd like to supply the text, I'll use my ASkME for you.

Also, I've racked my brains and music library and can't find anything.

It's okay, Monkey, I can wait 4 days. Thanks for the offer, though!

My pleasure.

"Straight into Darkness" by Tom Petty ... pretty literal, but a beautiful song.

I'm thinking maybe Richard Thompson's Galway to Graceland might fit? Also, possibly, Dark End of the Street?

What about Springsteen's Meeting Across the River? Has the feel of heading into the unknown.

After Hours / The Velvet Underground - or - Into the Night / Julee Cruise?

"Galway to Graceland" doesn't quite work, imho, because it is about a kind of mental disorder -- or at least a serious delusion -- and the protagonist is actually quite fancifully happy about going "to be with the King", even if we get a slightly sad and sympathetic tone as the listener. I didn't get any true darkness/starkness out of it in the same sense as "Richard".

Even so, this is a tenuous topic, but my thoughts/suggestions include

"Lost in Space" by Aimee Mann
"Left Bank" by Air
"Fearless" or "Will You Find Me?" by American Music Club
"Lonely Highway" or "The Dreaming Moon" by Magnetic Fields
"Walkin' After Midnight" by Patsy Cline

There are so many songs that have this feel - "Headshots" by Suzanne Vega; "Duk Koo Kim" by Sun Kil Moon; "Proposal" by Stina Nordenstam; "Big O Motel" by Tarnation; "Airwaves" by Thomas Dolby; "Deeper Into Movies" by Yo La Tengo - but don't quite hit the thematic nail on the head.

As much as I like musical questions, archagon, you seem to be new here, and so it might be worth reminding you that posting AskMe-style questions here when you've already asked an AskMe question this week isn't really what Metachat is for.

And how about Walt Dickerson's 'Alone in the Dark,' from Impressions of 'A Patch of Blue' (Jerry Goldsmith's score is good, but Dickerson's inspired-by album is better. And, of all the jazz instruments, the vibes might be the most into-the-darkness)?

"I've Had Her" by Phil Ochs
"The List" by Thea Gilmore
"Blue" by Lucinda Williams
"The Tide" by Lucy Kaplansky

"A Forest" by The Cure.

Sorry box, I didn't know this.

I have a playlist on my iTunes called Moody Opium Shuffle, reprinted below. It's a little alt- moody -soundtrack heavy, now that I look at it.

Whiskey Girl by Gillian Welch

The Poor Boy Is Taken Away by Richard & Linda Thompson

The Face of Love by Eddie Vedder/Nusrat Fateh Ali Khan (from the Dead Man Walking soundtrack -- very moody dark)

Pink flamingos by Rickie Lee Jones

Place to Be by Nick Drake

Such Great Heights by Iron & Wine

Naked As We Came by Iron & Wine

My Morphine by Gillian Welch

Opium by Marcy Playground

Altar boy by Rickie Lee Jones

Beat The Retreat by Richard & Linda Thompson

Know by Nick Drake

Dimming Of The Day/Dargai by Richard & Linda Thompson

Each Coming Night by Iron & Wine

Good Til Now by Gillian Welch

Pink Moon by Nick Drake

Ariel Ramirez by Richard Buckner

A Lack of Color by Death Cab For Cutie

Cold Wind by Arcade Fire

Breathe Me by Sia

Half Acre by Hem

The Devil Had A Hold Of Me by Gillian Welch

Fair by Remy Zero

Lucky by Radiohead

Don't Panic by Coldplay

Quiet Inside (The Jacket - Film Version) by The Jane Doe's

The Long Road by Eddie Vedder/M Khan/Nusrat Fateh Ali

The Great Valerio by Richard & Linda Thompson

Transatlanticism by Death Cab for Cutie

Promises by Lyle Lovett

The Ghost of Tom Joad by Bruce Springsteen

She Cries Your Name by Beth Orton

Oh, yes, I loove "Lost in Space" by Aimee Mann. Also Ghost World by Mann. I listened to that so often my friends told me to stop.

"Darkness makes me fumble
for a key
to a door
that's wiiiiiide open"

Paint it Black by the Stones - one of the best songs ever written about depression.

There's also CCKMP (also known as 'Cocaine Cannot Kill My Pain') by Steve Earle. Very dark. I was at this concert.