Saddest pop songs of the last 10 or so years

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Help me, The Lex! And the rest of ILM. I'm looking for those heartbreaking songs from folks like Mariah Carey and Madonna for a pal. I thought I had it pretty well handled until I realized that my taste in modern pop skews toward the upbeat, and even folks like Aaliyah (who I love) tend to come across more as fierce than wounded.

I'm outta my comfort zone here, so help me ILM!

― I eat cannibals, Thursday, 10 May 2007 17:22 (eighteen years ago)

live to tell

― Charlie Howard, Thursday, 10 May 2007 17:25 (eighteen years ago)

robyn - "be mine"

― sean gramophone, Thursday, 10 May 2007 19:14 (eighteen years ago)

I used to get real bummed out by "Torn." I think some of Dido's songs - "Here With Me" - are sad in a creepily codependant kind of way.

― kingkongvsgodzilla, Thursday, 10 May 2007 19:23 (eighteen years ago)

annie - heartbeat

― groovemaaan, Thursday, 10 May 2007 19:27 (eighteen years ago)

i keep meaning to put together a comp of pop ballads called something like "abjection" - i have a real soft spot for two types of sad pop ballad, 1) the crawling-on-floor tearing-hair-out ripping-new-emotional-wounds ones where the singing begs and pleads in vain for a boy to come back; 2) the very still, slightly unsettling staring-into-void blank ones. here are some of my favourites!

mariah carey - we belong together
mary j blige - be without you (oh just mary j's entire damn discography really)
kelis - get along with you
britney spears - everytime
lauryn hill - ex-factor
aaliyah - i care 4 u
brandy - i tried
all saints - never ever
all saints - black coffee
sugababes - run for cover
avril lavigne - i'm with you

i'm forgetting loads and loads cos i'm in a rush. i'll come back to this thread.

― lex pretend, Thursday, 10 May 2007 19:30 (eighteen years ago)

Annie's 'Heartbeat' again for me here.

Still quite poppy - Stereolab's 'The Black Arts'.

― Mister Craig, Thursday, 10 May 2007 19:32 (eighteen years ago)

Dream - "When I Get There" ("I got no hard feelings just the heart that needs healing")
Kleerup w/Robyn - "With Every Heartbeat"

My favourite song of all-time is in this genre, though it's nearing the 20-yr mark:

Nu Shooz - "Should I Say Yes"

― sw00ds, Thursday, 10 May 2007 19:38 (eighteen years ago)

Missy Elliott's "Teary Eyed" seems like it would fit well on Lex's list.

― o. nate, Thursday, 10 May 2007 19:44 (eighteen years ago)

Yeah, but Heartbeat is still pretty damn upbeat and seems to be a new love song more than one of misery and dissolution...

What I'm really looking for is modern equivalents of Rita White's "I Can't Give Back The Love I Feel For You," or Debbie Dean's "Stay My Love."

Closer in tone to I Care 4 U, but lyrically more like the abject misery of the best Country and Western songs. There's gotta be some R&B or pop out there that has a 'time to drink myself to death sobbing' vibe.

At least trying to do this has made me relisten to a lot of Annie and Aaliyah, which is brightening me up so much that I'm having trouble knocking this mix out!

― I eat cannibals, Thursday, 10 May 2007 19:50 (eighteen years ago)

Or closer to We Need a Resolution. Which, OMG, that's a great song too.

― I eat cannibals, Thursday, 10 May 2007 19:53 (eighteen years ago)

Anthony Hamilton - "I'm A Mess" fits the 'drink myself to death sobbing' bill...

"I' rather you'd slit me across the throat so I could die... / YOU DON'T WANT ME 'NO MORE...I'M A MESS RIGHT NOWWWW"

Also, "Iceberg" by Tweet is pretty sad to me...

― The Brainwasher, Thursday, 10 May 2007 19:56 (eighteen years ago)

'i care 4 u' is devastating! on the surface it's all about how she just wants to comfort her friend but really the emotional crux is her unrequited love for him.

brooke valentine - dying of a broken heart
ne*yo - so sick

― lex pretend, Thursday, 10 May 2007 20:06 (eighteen years ago)

haha amy winehouse is v good at this. search 'back to black', 'take the box'

― lex pretend, Thursday, 10 May 2007 20:07 (eighteen years ago)

Also, FAITH EVANS - I LOVE YOU.

― The Brainwasher, Thursday, 10 May 2007 20:10 (eighteen years ago)

I think that Silent Shout is quite a sad and dark pop record.

― the table is the table, Thursday, 10 May 2007 20:21 (eighteen years ago)

Yeah, particularly "From Off To On".

Also, Tweet "Motel" ("GO TO HELL BABY!, 'Cuz I know I saw u go into a motel.") and Rufus Wainwright "Memphis Skyline" (if that counts as pop)...

― The Brainwasher, Thursday, 10 May 2007 20:23 (eighteen years ago)

Oh, and "A Woman's Threat" by R. Kelly.

Okay, I'll stop now.

― The Brainwasher, Thursday, 10 May 2007 20:26 (eighteen years ago)

I would rather say "Heartbeat" competes with Kim Appelby's "Don't Worry" in the category for making happy and upbeat songs paying tribute after losing someone near to you.

― Geir Hongro, Thursday, 10 May 2007 22:29 (eighteen years ago)

I think you're forgetting Feeder's "LOL Drummer".

― Noodle Vague, Thursday, 10 May 2007 22:35 (eighteen years ago)

I'm not sure if it's "pop", but the one recent song that really made me cry is "Dance" by Nas. It's a song about him imagining one last dance in heaven with his deceased mother, and it ends up with a trumpet solo by his dad, Olu Dara, which really does it to me.

― Tuomas, Thursday, 10 May 2007 22:51 (eighteen years ago)

"La Ballade of Lady & Bird" by, um, Lady & Bird is the saddest song ever.

― ellaguru, Thursday, 10 May 2007 22:52 (eighteen years ago)

El Perro del Mar "Party". Actually, is it pop?
ah well, I love this woman.

― Drooone, Thursday, 10 May 2007 22:55 (eighteen years ago)

Tatu - Gomenasai
Kelly Clarkson - Beautiful Disaster

― aaron d.g., Thursday, 10 May 2007 22:58 (eighteen years ago)

finally heard "with every heartbeat", and it is amazing. my flatmate just wandered in and said, "you're into vocal trance now?" Am I?

― Gukbe, Friday, 11 May 2007 02:15 (eighteen years ago)

"Lost Cause" by Beck gets to me. So does "Carmichael" by Neil Young. "Waiting for a Superman" by the Flamig Lips, too. Shit, the whole of The Soft Bulletin, actually.

― Jiminy Krokus, Friday, 11 May 2007 02:34 (eighteen years ago)

Alicia Keys - If I Ain't Got You
Keyshia Cole - Love
Nelly Furtado - Say It Right

I'm missing sooo many.

― Tape Store, Friday, 11 May 2007 02:36 (eighteen years ago)

Yeah Yeah Yeahs - Maps

Basement Jaxx's "Romeo" doesn't make me sad, but if I paid attention to just the lyrics, I'd probably cry.

― Tape Store, Friday, 11 May 2007 02:45 (eighteen years ago)

"I'm not sure if it's "pop", but the one recent song that really made me cry is "Dance" by Nas. It's a song about him imagining one last dance in heaven with his deceased mother, and it ends up with a trumpet solo by his dad, Olu Dara, which really does it to me."

I meant "pop" in the broadest, "popular music" sense.

― I eat cannibals, Friday, 11 May 2007 02:49 (eighteen years ago)

love is a losing game - wmy winehouse
(as covered by prince last night in london)

― pisces, Friday, 11 May 2007 10:59 (eighteen years ago)

The Go Home productions boot mix of "Dub be good to me" crossed with "Let em in" brings out the sadness of the lyric, funnily enough.

― Mark G, Friday, 11 May 2007 11:03 (eighteen years ago)

Criminally overlooked, yet again: Rotterdam Termination Source - Poing

― StanM, Friday, 11 May 2007 11:04 (eighteen years ago)

Gwen Stefani, Cool. Yeah the lyrics are all +ve but the melody tells a different story.

― ledge, Friday, 11 May 2007 11:15 (eighteen years ago)

my flatmate just wandered in and said, "you're into vocal trance now?" Am I?

I doubt it

― RJG, Friday, 11 May 2007 11:18 (eighteen years ago)

Stan OTM

― Noodle Vague, Friday, 11 May 2007 11:52 (eighteen years ago)

Everytime is so raw. It's almost pathetic it's so vulnerable. Consequently it is so so beautiful. Lex OTM

― I know, right?, Friday, 11 May 2007 12:50 (eighteen years ago)

Probably something from Beck's "Sea Change"

― billstevejim, Friday, 11 May 2007 18:35 (eighteen years ago)

booka shade - in white rooms

― groovemaaan, Friday, 11 May 2007 19:04 (eighteen years ago)

jennifer paige - crush. best song ever.

― John Splith, Friday, 11 May 2007 19:39 (eighteen years ago)

robyn - "be mine"

For real - I was choking up when she played this at the Cargo gig recently.

― braveclub, Friday, 11 May 2007 19:59 (eighteen years ago)

B*Witched - Blame it on the Weatherman.

Call me soppy.

― AndyTheScot, Saturday, 12 May 2007 07:59 (eighteen years ago)

Or just inevitably out of touch.

― AndyTheScot, Saturday, 12 May 2007 07:59 (eighteen years ago)

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