I'll go with Depeche Mode's "Blasphemous Rumours" and "Somebody", talk about a double-whammy of a single!
Jon

I want to burn a cd of depressing pop songs like the following:

brandy - i tried
christina aguilera - walk away
justin timberlake - cry me a river
mario winans - i don't want to know
all saints - never ever, under the bridge, i know where it's at
britney spears - don't let me be the last to know
lauryn hill - ex factor
the fugees - ready or not

Where it isn't over the top singing, kind of meloncholy sounding. I like coldplay, radiohead, u2 but want some poppier songs.Please help

Ben Folds Five - Brick

Yeah , i get depressed when i hear those songs too. They're just so bad...

i always thought the fugees were rap. but, out of curiosity, why does that song depress you?

Bebel Gilberto - Lonely
Dido - My Lover's Gone
James (f/ Sinead O'Connor) - I Defeat
Joy Division - Love Will Tear Us Apart
Natalie Merchant - Seven Years
Nina Gordon - End of the World
The Cure - There Is No If
The Nields - Goodbye
U2 - Two Shots of Happy, One Shot of Sad
Zero 7 - Distractions
Billie Holliday - Gloomy Sunday

RS

Pehaps not exactly the same but see also:

• What songs help you feel depressed? [merged]

ONCE I WAS--TIM BUCKLEY (Jeff's dad)
GOODBYE--STEVE EARLE
SWEET OLD WORLD--LUCINDA WILLIAMS
TOM TRAUBERT'S BLUES--TOM WAITS

I can't believe nobody mentioned this one,

Sinead O'Connor - "Nothing Compares 2 U"

My choice was recently mentioned on a UK radio show, hence this bump, and I don't think has yet been included in this thread or the earlier one: Songs that make you cry, teary eyed, or emotional?

Gloomy Sunday

I would say

Arcade Fire's "Neighborhood #4 (7 Kettles)"

and

Bob Dylan's "Standing in the Doorway"

fit this thread to a T.

-ringding-

why would anyone WANT to be depressed?!!?!??!

American Lesion/Greg Graffin - Cease
Dire Straits - Brothers in Arms
Rush - Losing It
Van Halen - Crossing Over
Metallica - Fade to Black

An earlier poster said it well (or at least had a similar viewpoint as mine). Sometimes when your depressed, it's easier to work your way through it by exposing yourself to more depressing things (like music or movies). It helps you "get it all out" and confront your depression, and you feel better afterward, more so than if you listened/watched something happy. Different things work for different people.

One I hadn't seen listed here: Warren Zevon's "Keep Me In Your Heart". Bruce Springsteen has a lot of depressing songs: "The River", "Darkness on the Edge of Town", "Racing in the Streets", "Jungleland", all of "Nebraska", many more. That's enough for me ... I'm getting depressed just thinking about this

Holy crap, I feel for Ben on this one. I just listened to this on the train Friday and really got into the lyrics, and man, what a terrible thing. Ben says that the song is pretty accurate to what really happened - first girlfriend, first time being in love, first person you have sex with, and then that. Wow.

Another one, BTE's "A Lifetime", a little more upbeat, but still, the girl is dead.