“Sleepless Nights” (Everly Brothers song) covered by Elvis Costello.

I don’t know how pop is pop, but Tindersticks come to mind. Maybe “No more affairs” or “Tiny Tears.”

Anything by The Smiths or Morrissey :)

And Sinead O’ Connor’s rendition of (Prince’s) “Nothing Compares to You.”

Brick by Ben Folds 5

Who was

every breath you take by the Police
or
Stay by Shakespeare sister

Mother by John Lennon
Goodbye my lover by James Blunt
Dance (while the music still goes on) by ABBA
The same old sun by The Alan Parson Project

An oldie: “The Night the Lights Went Out in Georgia” I remember the first time I “got” the lyrics as a kid, I cried!

Tears In Heaven by Eric Clapton.

@trumi oooh, good one!

@lightlyseared everybreath you take isnt sad, its creepy. Very ummm stalker like.

I have to say, I have you all trumped with “If You Go Away”. The translation of (sorry about all the bad French spelling here) “Ne Me Qui d Pas” by Jacques Brell. Cyndi Lauper does a good version of it.

The volumes of albums by Chicago are what you listen to when you break up. Sad would be “How Do I Say Goodbye” by Boys II Men.

trumigoodboy wins this question. Look into to why Eric Clapton wrote that song.

Ooh yeah, donok, Jacques Brel was the master of sadness.

He was never well known in the States, which is truly our loss. For those of you whonever don’t know him, he was a Belgian singer who was as much a physical performer as a vocal artist. Watching him sing is an incredibly powerful experience. He literally incarnates the songs he sings. Rips me to shreds.

You owe it to yourselves to watch this video from his most famous concert performance (French w/subtitles)

Ces Gens La

@uberbatman whats sad is everyones insistence at playing it at weddings. I mean really you’d think they’ve never listened to it.

The most depressing song I’ve ever heard is Alone Again, Naturally by Gilbert O’Sullivan. Every time it comes on the car radio I want to drive my car into the abutment.

@wildflower- I love The Same Old Sun by APP. But I don’t think of it so much as sad, but as triumphant, at least the way the song ends. Hell, I love anything by APP.

@Astrochuck! I totally forgot about that song! “I promise myself to treat myself to visit a nearby town, and climbing to the top, throw myself off, in effort make it clear to whoever what it’s like when your shattered…” Oh man it doesn’t get much sadder than that. I can’t believe that song was ever a hit!

@AC: It is quite lonely and sad….but a great tune nonetheless! and yea, I’ll go along with anything by APP is good music (particularly Don’t answer me and Limelight)!

I’d either have to say Unbreak My Heart by Toni Braxton or Last Kiss by Pearl Jam (the original was Wayne Cochran).

I don’t know if you’d consider those “pop” but they were both played on pop channels.

The Future by Leonard Cohen

My Immortal by Evanessence

The Flaming Lips – Do You Realize??
Radiohead – Videotape
U2 – Sunday Bloody Sunday

Depression era song by Billie Holiday
“Gloomy Sunday” (The Suicide Song) banned from being played on the radio.

I definitely second “Alone Again (Naturally)”. Also… “Busby Berkeley Dreams” by the Magnetic Fields, or really anything by the Magnetic Fields, “Invisible Ink” by Aimee Mann, and “Braille” by Regina Spektor.

Philadelphia by Bruce Springsteen

Hallilujah sung by Jeff Buckley, written by Leonard Cohen

No Cure for Love by Leonard Cohen

Come to think of it, almost anything by Leonard Cohen!

Shannon- Link

Hated that song as a kid. The dog dies.

against all odds- phil Collins

David Gates (from Bread) was a neighbor of mine in CA and oddly enough, the guy was one of the most upbeat people I knew. I guess he poured it all out in his songs!

I think Tears in Heaven has to be it

Sorry to be contentious, but I think Tears in Heaven is disgusting. And yes,
I know the story. But like many of Clapton’s lyrics, the verses are all entirely about HIM, none about the kid. Pfaugh.
So, having made myself a pariah, I’d offer “Somewhere Out There”, recorded
in 1988 or so by Linda Ronstadt and some guy. Boo hoo hooo hoooooooooo!

Somewhere Out There is an inspired choice! The back story on that is that the song was used in a Sesame Street movie and Big Bird was singing it to Snuffy while they were apart. Big Bird ran away or something. Hope that doesn’t ruin it for you. I remember my 5 year old hearing the song and then wanting to go rescue Big Bird from Out There!

Oh, and the reference to Sesame Street reminds me of Kermit the Frog from the Muppets singing “It’s Not Easy Being Green”. That song made me sad.

Hard for me to to pick juts one but this one just does it for me!
Have You Forgotten – Red House Painters

Very Very close runners up:
Lover, you shouldn’t have come over – Jeff Buckley
Everybody Hurts – REM
Goddamn the Sun – The Swans
Famous Blue Raincoat – Leonard Cohen
Pictures of You – The Cure