Depress and sadden me with your beautiful melodies.

April 22, 2007 8:00 PM

How about recommending some songs like "Everybody's Talkin' at Me" from Midnight Cowboy? I explain more inside.

Last night I saw Midnight Cowboy for the first time and now I cannot stop listening to the "theme song" sung by Harry Nilsson, "Everybody's Talkin' at Me." I have a weakness for sad/intense ballad-y, lonely (yet beautiful, melodious) songs. Examples include "At My Window Sad and Lonely" by Billy Bragg and Wilco, "Into My Arms" by Nick Cave and the Bad Seeds, "The Weight" by the Band, "Hallelujah" by Jeff Buckley, and even "Angeles" by Elliot Smith or "Fade into You" by Mazzy Star.

As you can see, I have a short playlist but I really would like to expand it. I am mostly a rap/hip hop listener, so I sort of don't even know where to begin. Rather than investigate various bands' discographies for just the right thing, I was hoping folks could recommend a single here, a single there, that falls into this category. I know I hit on country, alt. country and even emo here, but that basically means I am open to anything (but, bonus points for country/folky). I have looked at similar AskMe threads on this and found some okay stuff, but not exactly right and I'd love more.

Thanks a lot in advance.

posted by sneakin to media & arts (74 comments total)

Leonard Cohen, yo.
posted by zamboni at 8:09 PM on April 22, 2007 [1 favorite has favorites]

Btw, artists and track titles are super helpful. Meant to say that originally. Thanks!
posted by sneakin at 8:12 PM on April 22, 2007

Pretty much everything by Nick Drake. It's all good.
posted by runtina at 8:19 PM on April 22, 2007

"Voices Carry" by Til Tuesday.
"Lovers of Today" by The Pretenders.
"Wise Up" by Aimee Mann.
"Misfits" by The Kinks.
"Word on a Wing" by David Bowie.
"The Hurting" by Tears For Fears.
"Hearts and Bones" by Paul Simon.
"San Jacinto" by Peter Gabriel.
"Take the Long Way Home" by Supertramp.
"Ordinary World" by Duran Duran.
"Smalltown Boy" by Bronski Beat.
"I STill DO" by The Cranberries.
"The Gift" by Annie Lennox.
"That Day Is Done" by Elvis Costello.
"MMM MMM MMM MMM" by Crash Test Dummies.
"Tiny Dancer" by Elton John.
"Nightswimming" by REM.
"Will Never Marry" by Morrissey.
"Pullin' Back The Reigns" by kd lang.
"Oh Father" by Madonna.
"Desperadoes Under The Eaves" by Warren Zevon.

Feels good to cry sometimes.
posted by Dizzy at 8:29 PM on April 22, 2007

"This Woman's Work" by Kate Bush.
"Love Got Lost" by Joe Jackson.
"5:30 Train" by The Supremes.
"Shine" by Tracy Bonham.
"To Sir, With Love" by Lulu.
"Mystery Train" by Elvis Presley.
"Sullen Girl" by Fiona Apple.
"Breathe" by Anna Nalick.
"Isolation" by John Lennon.
"Dear God" by XTC.
"Since I Fell For You" by Lenny Welch.
"Carbon Monoxide" by Regina Spektor.
"Bittersweet Symphony" by The Verve.
"Clever" by Jill Sobule.

Now dry your eyes.
It'll be alright.
posted by Dizzy at 8:42 PM on April 22, 2007

"Long Long Time" by Linda Ronsdadt.
"Oh Lonely Soul, It's a Hard Road" by Mary's Danish
posted by sourwookie at 8:43 PM on April 22, 2007

Alone Again (Naturally) by Gilbert O'Sullivan

I Just Wasn't Made For These Times by The Beach Boys (and the rest of the album Pet Sounds)

Jackass by Beck

Brick by Ben Folds

Town Cryer by Elvis Costello (a lot of good Elvis stuff in this category)

Wicked Little Town from Hedwig and the Angry Inch

...and then listen to Everybody's Talkin eleven more times. That is a damn good song.
posted by SampleSize at 8:44 PM on April 22, 2007

- Elephant Gun by Beirut
- Displaced by Azure Ray
- Neon Bible by Arcade Fire (extraordinary performance here in an elevator)
- Nico: Little Sister, I'll Keep It With Mine, These Days, Fairest of the Seasons
- Nick Drake: Pink Moon, Cello Song, Northern Sky
- Everybody's Got To Learn Sometime, Beck
- In the Aeroplane Over the Sea by Neutral Milk Hotel
- Radiohead: Fake Plastic Trees, High and Dry
- Sally Ann by Rufus Wainwright
- Track You Down by Sondre Lerche
- You've Got Her In Your Pocket by the White Stripes
- 405 by Death Cab for Cutie
- Sunsets by the Concretes
- Bookends by Paul Simon (dangerously melancholy)
posted by JamesToast at 8:45 PM on April 22, 2007

"If You Could Read My Mind" ~ Gordon Lightfoot
"Southern Cross" ~ Crosby, Stills & Nash
posted by amyms at 8:47 PM on April 22, 2007

Townes Van Zandt

Scott Walker

Rolling Stones: "Wild Horses," "Dead Flowers," all of Exile on Main Street and most of Beggars Banquet.

"Katie's Been Gone" by the Band, it's on the Basement Tapes

The Silver Jews, especially the second and third albums, Natural Bridge and American Water.

Skip Spence, the album Oar (esp. "Weighted Down (The Prison Song)" and "Cripple Creak").

Skip James (esp. "Crow Jane").

Leadbelly
posted by pablocham at 8:48 PM on April 22, 2007

"Mona Lisas and Mad Hatters" ~ Elton John
posted by amyms at 8:49 PM on April 22, 2007

Any number of Big Star or Chris Bell songs, especially:
-What's Going Ahn
-Back of a Car
-Ballad of El Goodo
-Take Care
-Better Save Yourself
-I Am the Cosmos

...and seconding Pet Sounds, XTC, Neutral Milk Hotel, Elvis Costello.
posted by equalpants at 8:52 PM on April 22, 2007

Specific tracks, eh? Well, you're off to a good start by yourself.

Suzanne, Leonard Cohen (Songs of Leonard Cohen)
Grace, Jeff Buckley (Grace)
Birds & Ships, Billy Bragg & Wilco (Mermaid Avenue)
Dame, a qui, Gothic Voices/Colin Scott Mason (Mirror of Narcissus)
The Book of Love, Magnetic Fields (69 Love Songs)
New York Mining Disaster 1941, Chumbawamba (WYSIWYG)
Killing Floor, Cloudstreet (Dance Up The Sun)
Such Great Heights, Iron & Wine (Such Great Heights)
Buy Now Pay Later (Charlie No. 2), The Whitlams (Eternal Nightcap)
Fallen For You, Sheila Nicholls (Brief Strop)
I Just Don't Think I'll Ever Get Over You, Colin Hay (Transcendental Highway)

(Note: slight .au bias, and some are covers and/or aren't typical of the artist as a whole.)
posted by zamboni at 8:52 PM on April 22, 2007

Can't believe you put REM without putting Everybody Hurts.

I Believe - Blessed Union of Souls

...I'll keep thinking.
posted by Industrial PhD at 8:56 PM on April 22, 2007

"Theme From Midnight Cowboy" - Faith No More (Note: this is a gorgeous instrumental at the end of their album Angel Dust. I have never seen Midnight Cowboy, so I don't know if this piece of music was actually in the film.)

Continuing on:
"Take This Bottle" - Faith No More
"What We Really Want" - Rosanne Cash
"Wildwood Flower" - June Carter Cash and/or Reese Witherspoon
(Another note: the above are quite country-tinged.)
"Don't Dream It's Over" - Crowded House
"Breathe Me" - Sia
"Ex Factor" - Lauryn Hill
"The Beautiful Ones" and "Purple Rain" - Prince
"Sweet Jane" - Cowboy Junkies
"In My Life" - the Beatles
"The Rainbow Connection" - Sarah MacLachlan and/or Jim Henson
"When It's Cold, I'd Like to Die" and "Porcelain" - Moby
"Wonderwall" - Oasis.
posted by princesspathos at 8:57 PM on April 22, 2007

I've always been partial to "Take Me Back" by Bonnie Tyler. It's a high-voltage power ballad, but it sticks with me like Nilson and Elton John...
posted by lhauser at 8:57 PM on April 22, 2007

I could go on for hours. Also see:
Nirvana: Unplugged in New York in its entirety.

"Trailer Trash" and "Bankrupt on Selling" - Modest Mouse, The Lonesome Crowded West.

"Ladies and Gentleman We Are Floating in Space" - Spiritualized.

"Goodbye Yellow Brick Road" - Elton John

"Will The Circle Be Unbroken?" - I really like the version from the Staple Singers. On the other hand, you're probably aware that it's a country/folk chestnut.
posted by princesspathos at 9:05 PM on April 22, 2007

Ray Charles and Willie Nelson singing "Seven Spanish Angels".

"Pancho and Lefty", by Townes Van Zandt.

Johnny Cash's version of "Hurt".

(And JamesToast, that Arcade Fire video is revelatory. Fucking great.)
posted by BitterOldPunk at 9:07 PM on April 22, 2007

spiritualized. just about anything by them, but in particular a handful of songs from "Ladies and Gentlemen We Are Floating in Space" come to mind. The title track is one, as is Cool Waves, and I Have A Broken Heart.
posted by shmegegge at 9:07 PM on April 22, 2007

Hey, you and I like the same songs! I grew up in the seventies and my parents loved that sort of thing, so this list is heavily influenced by that. I put a few of these on my most recent MeFi mix. Email me your address and I'll send it to you.

"don't think twice it's alright" bob dylan
"reuben and cherise" grateful dead
"she sang hymns out of tune" nilsson again
"you can close your eyes" linda rondstat
"cats in the cradle" harry chapin
"operator (that's not the way it feels)" jim croce
"house carpenter" dave van ronk (many people do it)
"weightless again" handsome family
"springhill mining disaster" u2 (covers someone else)
"the wreck of the edumnd fitzgerald" gordon lightfoot
"four in the morning" jesse colin young
"this one or that one" six parts seven
"by way of sorrow" cry cry cry
"silver dagger" or "diamonds and rust" joan baez
"I wish my baby was born" be good tanyas
"freedom hangs like heaven" iron & wine
"pocketful of money" jens lekman
"trouble" cat stevens
"thirteen" wilco
"dressed in brown" crooked jades

pretty much anything by Joel RL Phelps, but I suggest the Warm Springs Night album.
posted by jessamyn at 9:12 PM on April 22, 2007 [2 favorites has favorites]

"Birds" - Neil Young
posted by Neiltupper at 9:25 PM on April 22, 2007

Bright Eyes. Almost any track on I'm Wide Awake It's Morning will do you right, seriously. Or, Ani DiFranco perhaps? Take 'Gravel' on Little Plastic Castles as one of many examples.
posted by fieldtrip at 9:26 PM on April 22, 2007

"I Don't Want to Talk About It" - Indigo Girls (from the film Philadelphia)
posted by gt2 at 9:41 PM on April 22, 2007

"New York Mining Disaster, 1941" was actually a hit for the Bee Gees on their first album, which you may also like.
posted by rhizome at 9:47 PM on April 22, 2007

The entire "Harvest Moon" album by Neil Young especially the "Unknown Legend" song.
posted by Maishe at 10:09 PM on April 22, 2007

Eurythmics: "The Walk" "I Could Give You a Mirror" "Somebody Told Me" "Who's that Girl".
The Cure
posted by brujita at 10:16 PM on April 22, 2007

Jawbreaker - Unlisted Track (on Dear You)
Leonard Cohen - Chelsea Hotel No. 2
The Lucksmiths - If You Lived Here You'd Be Home Now
Black Sabbath - Planet Caravan
Erik Petersen - Old Time Memory
Patti Smith - Elegie


For an unorthodox approach: Brian Eno - Golden Hours
posted by nasreddin at 10:20 PM on April 22, 2007

Chumming the Ocean- Archers of Loaf
This Must Be the Place- The Talking Heads
If You Want to Sing Out, Sing Out- Cat Stevens
Motor Away- Guided by Voices
So Long, Marianne- Leonard Cohen
Foaming Love- Bedhead
Gold Day- Sparkehorse
posted by macrowave at 10:25 PM on April 22, 2007

Palace Music - Gulf Shores (from Lost Blues & Other Songs) Will Oldham has tons of stuff that fit the bill. He's recorded under a lot of different names, but lately seems to be sticking to Bonnie "Prince" Billy. For some of his bleakest moments, check out I See a Darkness.
posted by hydrophonic at 10:30 PM on April 22, 2007

Two by Mary Chapin Carpenter, from Stones in the Road:
"The End of My Pirate Days"
"This is Love"

"River" by Joni Mitchell - her version, or the Indigo Girls version

"Midnight Blue" by Melissa Manchester
posted by jeri at 10:49 PM on April 22, 2007

"Broadway Hotel" - Al Stewart
"Day After Day (The Show Must Go On)" - The Alan Parsons Project
"Coming Up Close" - 'Til Tuesday
"Short Stacks" - The Dittybops
"Spinning" - Zero 7
"Swords and Knives" - Tears for Fears
"Vera Lynn" - Pink Floyd
"Hope" - Beverley Craven
"Same Old Sun" - The Alan Parsons Project
and lots and lots from Simon and Garfunkle...
posted by OneOliveShort at 10:51 PM on April 22, 2007

Well, you already have hundreds of songs at your disposal, what's a few more? Two albums to consider:

Lost In Space by Aimee Mann, who has always had a flair for quiet drama. Even the liner notes, filled with illustrated vignettes for each song, have the sort of sad, longing quality you seem to seek. ("Invisible Ink," "This Is How It Goes" and "It's Not" if you have to pick three.)

Kristin Hersh's Strange Angels is a bit spare and her voice is unique, but if you get past that you'll find a rewarding album of her peculiar brand of folk music. ("Home," "Hope" and "Heaven.")

Selected songs:
"Lodestar," Sarah Harmer. (If you only grab one, grab the Aimee Mann. If you only grab two, get this too.)
"Sleepy Little Sailor," Oh Susanna. (But you might want to buy Johnstown first if you want more of the same.)
"Rougher," Lois. (Featuring Elliott Smith.)
"There Is a Light That Never Goes Out," the Lucksmiths. (Originally by the Smiths, but this one might suit you better.)

Finally, thirding the Neutral Milk Hotel album. It's not quite what you're looking for, and yet it's perfect.
posted by chrominance at 11:17 PM on April 22, 2007

There's a looot of alt-country that you will probably like.
The Handsome Family - start with album In the Air (song "So Much Wine" is one great one from that album)

Neko Case - start with album Furnace Room Lullaby (song "Thrice All American" is one great one from that album)

The Mountain Goats


get Magnetic Fields' giant album 69 Love Songs; expensive but worth it. One good heartbreaker from that album is "Papa was a Rodeo"; there are plenty, though, mixed in with lots of happy ones.
posted by LobsterMitten at 11:50 PM on April 22, 2007

David Berkeley: Fire Sign
Michael Johnson: Ghost In This House (the live recording on The Folkscene Collection is really pretty)
Morphine: Gone For Good
Beth Nielson Chapman: Sand and Water, Seven Shades of Blue, Years
Greg Brown: Banjo Moon
Randy Newman: I Think It's Going To Rain Today
Anders Osborne: Me & Lola, Ash Wednesday Blues
Tom Waits: Waltzing Matilda
Lucinda Williams: Here In California
Tom Russell: California Snow
Johnny Cash: Give My Love to Rose
Regina Spektor: Samson
Kris Kristofferson: Sunday Mornin' Comin' Down
Kate Wolf: The Lilac & The Apple, In China Or A Woman's Heart
Hem: Betting On Trains
Grey Delisle: Beautiful Mistake
Delbert McClinton: I've Got Dreams to Remember
Brad Paisley & Alison Krauss: Whiskey Lullaby
Fred Eaglesmith or the Catherine Britt cover: Drive-In Movie
Emmylou Harris: My Antonia
Willie Nelson: Seven Spanish Angels
Richard & Linda Thompson: Dimming of the Day,
Bonnie Raitt & Jackson Browne: My Opening Farewell
Nanci Griffith: Late Night Grand Hotel, Always Will -- a ton of her stuff actually. The Dust Bowl Symphony Album versions of her songs are gorgeous with the symphony backing.
posted by diamondsky at 12:18 AM on April 23, 2007

Blendcrafters - Bad Luck Blues
posted by phrontist at 1:25 AM on April 23, 2007

You might be interested in "I Guess The Lord Must Be In New York City" also by Harry Nilsson which was originally intended to be the theme for "Midnight Cowboy".

Also, you really need to listen to some James Taylor. I love "Hey Mister That's Me Up On The Jukebox" and "Riding on a Railroad" and there's loads of other great stuff on the same album - "Mud Slide Slim And The Blue Horizon".
posted by teleskiving at 1:47 AM on April 23, 2007

Get Patsy Cline's 12 Greatest Hits, on which every single track fits your criteria, sneakin.
posted by cgc373 at 1:47 AM on April 23, 2007

Tom Waits - On the Nickel

The album "Broke Down" by Slaid Cleaves is excellent, my girlfriend hates when I listen to it because of how depressing it is.

Of course we can't forget my favorite band (who also has some rather sad songs):

Wrinkle Neck Mules (Minor Enough): Big Dipper
Wrinkle Neck Mules (Minor Enough): Head of Steam
Wrinkle Neck Mules (Pull the Break): Lowlight
Wrinkle Neck Mules (Pull the Break): Weeps

The Mules are a indi-rockish alt.country band with some bluegrass roots. They have a unique sound and well written lyrics.
posted by elricbillman at 2:10 AM on April 23, 2007

Cry Cry Cry - Cold Missouri Water
Cry Cry Cry - Shades of Gray
posted by elricbillman at 2:17 AM on April 23, 2007

Scott Walker : Scott 1, 2, 3, & 4
Talk Talk : Spirit of Eden
John Cale : Hallelujah ( a superior version IMHO )
Leonard Cohen : Ten New Songs
While your'e at it check out The Dolphins and the original of Everybody's Talkin by Fred Neil.
posted by Dr.Pill at 2:28 AM on April 23, 2007

Emmylou Harris: Pretty much all of Red Dirt Girl, but especially the title track, plus My Baby Needs A Shepherd and Bang The Drum Slowly
Gillian Welch: Orphan Girl and Annabelle on Revival, and then Elvis Presley Blues on Time: The Revelator which is not devastatingly sad, but definitely melancholy, and soooo gorgeous.

But the big winner for me:
Ryan Adams: Oh My Sweet Carolina

That song makes me bawl like a baby. Course I'm from the South.

(These are all solidly in the country-folky realm, and all quite beautiful, and not that twangy.)
posted by bluebird at 3:36 AM on April 23, 2007

Oh my gosh, how could I forget John Prine's Angel from Montgomery, especially the version with him and Bonnie Raitt.

Bruce Springsteen's Paradise on The Rising, too.

Um, this is really fun. Great question!
posted by bluebird at 3:38 AM on April 23, 2007

Eliza Gilkyson: Tender Mercies

OK, I have to stop. Have to stop.
posted by bluebird at 3:40 AM on April 23, 2007

These are all so amazing. I have a lot of work to do now. Thanks everyone. School is ending so as I get my hands on these tracks and listen to them I'll come back and let you guys know how I fared.

Oh, and, keep 'em coming!
posted by sneakin at 4:14 AM on April 23, 2007

Cry Cry Cry is a great suggestion - if you like them, definitely check out Richard Shindell solo. Just about anything would fit your bill, I think, but try "A Summer Wind, A Cotton Dress" or "Reunion Hill" for starters.

Also: Polaroids by Mary Lou Lord; Adelaide by the Old 97s. (If that's a winner there's more on the same album, Drag It Up: Valium Waltz, In the Satellite Rides a Star.)
posted by clavicle at 4:33 AM on April 23, 2007

FWIW, if Leonard Cohen's voice is a bit grating for you, try the 1987 tribute album "Famous Blue Raincoat" by Jennifer Warnes. (Jenny sings Lenny)
posted by Robert Angelo at 4:42 AM on April 23, 2007

You might also like Jenny's "Shot Through The Heart" album, especially the tracks, "Sign On the Window" and "You Remember Me."
posted by Robert Angelo at 4:44 AM on April 23, 2007

I'd recommend other songs by Fred Neil who wrote the song you like so much. Bleeker and MacDougal is an excellent album.
posted by piratebowling at 5:16 AM on April 23, 2007

Kansas, "Dust in the Wind"
Bread, "It Don't Matter to Me"
Pure Prairie League, "Aimee"
Gordon Lightfoot, "Your Love's Return"; "Early Morning Rain"; "If You Could Read My Mind" (ok, everything Gordon Lightfoot's ever done)

Wow, I must be really old.
posted by Saucy Intruder at 5:29 AM on April 23, 2007

The album you want is "Nilsson Sings Newman". Nilsson applies that voice to Randy Newman songs. Beware though, the whole thing is only about 25 minutes long.
posted by DarkForest at 6:19 AM on April 23, 2007

First of all, I really, really envy you for having seen Midnight Cowboy for the first time. And you really must listen to Glen Campbell's Wichita Lineman. (visually calming youtube link) Then play it every day for a couple of years and if you think you know this song, try to find the acoustic Johnny Cash version. You'll be crying like the first time you heard it. At least that's what happened to me.
posted by ouke at 7:02 AM on April 23, 2007 [1 favorite has favorites]

"Mystery," Indigo Girls. Perfect for end-of-summer longing/sadness. Or anytime, really.
posted by Bud Dickman at 7:06 AM on April 23, 2007

I'm a big fan of Patty Griffin, not least because of her beautiful sad songs:

Rain "Strange how hard it rains now. Rows and rows of big dark clouds."
When it Don't Come Easy "If you break down I'll drive out and find you. If you forget my love I'll try to remind you."
Long Ride Home "Forty years go by with someone laying in your bed. Forty years of things you wish you'd never said. How hard would it have been to say some kinder words instead, I wonder as I stare up at the sky turning red."
Useless Desires "Say goodbye to the old building that never tried to know your name. Goodbye, goodbye, goodbye old friend, you won't be seeing me again. Goodbye to all the window panes shining in the sun like diamonds on a winter day. Goodbye, goodbye to everyone."
posted by booth at 7:08 AM on April 23, 2007

Speaking of "Wichita Lineman," I was at an R.E.M. concert in Houston in 1995 and they covered that song.

Later they released that night's recording of the song on the CD single of "Bittersweet Me." I was kind of stoked.

Anyway, that version is good as well.
posted by Bud Dickman at 7:08 AM on April 23, 2007

Basically, you want Leonard Cohen's first three albums, or The Best of.... plus Harvest and After the Gold Rush by Neil Young.

Emily Haines - "Crowd Surf Off a Cliff" (youtube, ignore the visual)
Sia - "Breathe Me"(youtube, ignore the visual)
Bob Dylan - "Boots of Spanish Leather"
The Cure - "Pictures of You"
Galaxie 500 - "Blue Thunder", "Fourth of July"
The Walker Brothers - "The Sun Ain't Gonna Shine Anymore" and "Make It Easy On Yourself"
Just about everything on Opal's Early Recordings , esp "Harriet Brown" and "All Souls"
"Nobody 'Cept You" originally by Bob Dylan, covered by the Waterboys and 16 Horsepower
"Bloodstreamruns" by Nature & Organization
posted by Martin E. at 7:20 AM on April 23, 2007

lastly, "Philadelphia" by Neil Young (bonus: Tori Amos version)
posted by Martin E. at 7:25 AM on April 23, 2007

oh, hell, that first Philadelphia isn't the original...oops. You'll have to find it another way.
posted by Martin E. at 7:28 AM on April 23, 2007

The Eagles, "Desperado"
The Beatles, "She's Leaving Home"
posted by DevilsAdvocate at 9:44 AM on April 23, 2007

"Komm, süsser Tod (Come Sweet Death)" by Arianne and Shiro Sagisu.
"Stirb Nicht Vor Mir (Don't Die Before I Do)" by Rammstein.
"Gone" by Sarah Cracknell.
"Cry" by Godley & Creme.
"Only the Lonely" by The Motels.
"Drive" by The Cars.
"Expecting to Fly" by Buffalo Springfield.
"Don't Let the Sun Catch You Crying" by Gerry & the Pacemakers.
"Going Out of My Head" by Little Anthony & the Imperials.
"Long Gone" by Syd Barrett.
"The End of the World" by Skeeter Davis.
"Something I Can Never Have" by Nine Inch Nails.
"Trouble" by Coldplay.
"Estranged" by Guns N' Roses.
"Eleanor Rigby" by The Beatles.
"Goodbye to Love" by The Carpenters.
"Live Bed Show" by Pulp.
"Digging in the Dirt" by Peter Gabriel.
"Is That All There Is?" by P J Harvey.
"Ordinary World" by Duran Duran.
"Today" by Jefferson Airplane.
"A Rose for Emily" by The Zombies.
posted by zebra3 at 10:00 AM on April 23, 2007

Big Star - "Thirteen"
The Byrds - "He was a friend of mine"
Yo La Tengo - "The Summer"
Daniel Johnston - "Peek A Boo"
posted by Andy Harwood at 10:08 AM on April 23, 2007

Lots of Willie Nelson songs fit this description. Pick up his Crazy: The Demo Sessions. You won't regret it.

Also, I have a hunch you'd love Neil Cleary. He's an alt country singer who just drips that you-dumped-me-so-I'm-going-to-play-by-guitary-really-loud ethos. Get his album Numbers Add Up.
posted by roll truck roll at 10:44 AM on April 23, 2007 [1 favorite has favorites]

Grant Lee Buffalo ("Demon Called Deception")
Gov't Mule ("Soulshine")
posted by parilous at 12:50 PM on April 23, 2007

"Ghost" by Indigo Girls
posted by tuffbunny at 2:22 PM on April 23, 2007

Seconding the Gillian Welch recommendations,
Also:
Every Night About This Time, Blue Wing, and Little Honey by Dave Alvin
Till a Tear Becomes a Rose by John Prine
La Sirena by Los Superseven
Bill Withers Ain’t No Sunshine
Till I’m Too Old To Die Young by Kieran Kane and Kevin Welch
One Time One Night and La Pistola Y El Corazon by Los Lobos
Timeless is a tribute album to Hank Williams, lots of good stuff on it.
posted by Killick at 6:02 PM on April 23, 2007

Oh yeah for Jennifer Warnes' Famous Blue Raincoat. Damn she has a voice. And Lenny's tunes.
posted by pointilist at 9:30 PM on April 23, 2007

The saddest most hauntingly beautiful song I ever heard was Galaxie 500's cover of (New Order's) Ceremony.
posted by Slarty Bartfast at 9:38 PM on April 23, 2007

I feel I need to add "Song to the Siren". The cover by This Mortal Coil is good but the original Tim Buckley version is folky and, to me anyway, pretty much the saddest thing ever.
posted by lornoss at 6:25 AM on April 24, 2007

Lately I've been finding the recent cover of "Handle me with care" (by Jenny Lewis et al) has this same sad/wistful effect on me. Not sure if it does that for everyone, but once I hear this I'll be humming it all week. Here's a blog with a link to an audio version, but I haven't checked their link...link
posted by LobsterMitten at 9:45 AM on April 24, 2007 [1 favorite has favorites]

Ok, better link. The Jenny Lewis album, which has several good songs for you. Also, the original from the Traveling Wilburys.
posted by LobsterMitten at 9:58 AM on April 24, 2007

hi,
didn't check all previous answers, so I'm maybe only repeating someone's advice..

try the "tap the red cane whirlwind" album, by kelly joe phelps. He sings three or four ballads in this that will do the trick, I think.


posted by nicolin at 3:21 AM on April 29, 2007

forgot the link :

kelly joe phelps
posted by nicolin at 3:22 AM on April 29, 2007

Tom Waits' "I Hope That I Don't Fall In Love With You"
posted by vytae at 1:22 PM on May 4, 2007

Lucero — "Drink Til We're Gone"

You might be able to hear it here (track #5). They are tagged as "alt-country".
posted by hooray at 8:42 PM on May 10, 2007

Oops, I left out the link.

You can listen to it here.
posted by hooray at 8:43 PM on May 10, 2007