5. Wilco, "I Am Trying to Break Your Heart" (2002)

Jeff Tweedy often seems to be trying to obscure his emotional songwriting with avant-garde touches like weird ambient sounds, deliberately "wrong-sounding" notes, and obtuse lyrics. But none of those elements can stop "I Am Trying to Break Your Heart" from succeeding in its titular aims. — A.H.

 

4. The Strokes, "Someday" (2001)

Equal parts regret and boozy barstool philosophy, "Someday" is a broadly focused portrait of a breakup. Though the line "alone we stand, together we fall apart" hints at a relationship dissolved for its own good, the song is as much about letting go of youth as it is about letting go of someone, and Julian Casablancas' disaffected croon obscures some of his most painfully sincere lyrics. — A.H.

 

3. Justin Timberlake, "Cry Me A River" (2002)

Who ever would've thought that the dopey fresh-faced bleach-blonde kid from 'NSYNC would grow up to have this much soul? If JT wants me to cry, damn it, I'm cryin'. — J.G.

 

2. Amy Winehouse, "Tears Dry On Their Own"

The juxtaposition of the music from Marvin Gaye and Tammi Terrell's classic "Ain't No Mountain High Enough" and Winehouse's self-penned lyrics and melody is the first thing you're likely to notice about this song. But last year's Lioness: Hidden Treasures revealed the original version of "Tears," and shockingly, it didn't matter that much — Winehouse's desperate, lonely vocal was just as evocative and touching as ever, proving that no matter how many people accused her of slavish pastiche, Winehouse's voice was always her own. — A.H.

 

1. Outkast, "Ms. Jackson"

This is probably the only breakup song ever addressed to the singer's mother-in-law, but the gambit pays off. By directing his imploring lines to Erykah Badu's mom instead of Badu herself, Andre 3000 makes an implicit statement about how the idealism of young love ("that crib with the Goodyear swing") gives way to the complexities of adulthood: private schools, day care, lawyers. Mothers-in-law. It's rueful, but it's loving too. — P.S.

 

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Tags Breakups

Commentarium (55 Comments)

Apr 23 12 - 1:10am
abloob

The first songs that came to mind for me were:

- Heartbeats by The Knife
- Little Motel by Modest Mouse
and, most of all:
- The Boy Who Blocked His Own Shot by Brand New

Still don't disagree with this list, and it's a lot more difficult to write a list for the 00's due to the sheer variety of music available.

Apr 23 12 - 12:17pm
Alex Heigl

Yeah. It's interesting, though -- with the '00s, people are a lot nicer. There's less vitriol and more genuine interest in sharing songs: I've picked up some great reader recommendations from the later lists.

Apr 23 12 - 2:00am
Show

I might have done All I Want for LCD instead of someone great. But that's a mere matter of preference for one song (slightly) over the other. Good list though.

Apr 23 12 - 3:06am
Ariel

"sleep all summer" by national and st. vincent

Apr 23 12 - 5:14am
yep

Good list.

I know this is just me, since the whole rest of the world seems to love it, but I just find the cutesy non-rhyme in Mr Brightside (where he almost but then doesn't say "she's touching his dick") just too coy and twee. Ruins the whole song for me. I prefer Lily's potty mouth, I guess.

If this global industry were less US- and UK-centric, I'd have hoped to see Missy Higgins's 'Scar' here, such a great chronicle of growing wiser from bad, controlling relationships. Plus 'Wish You Well' by Bernard Fanning ("why'd you give up on me so soon?").

Apr 30 12 - 11:39pm
right

"Where I Stood" would have worked, too.

Apr 23 12 - 8:13am
Miles Forrester

The Past Is A Grotesque Animal: Of Montreal. 12 Minutes of Pain.

Apr 23 12 - 1:11pm
lalalanicelady

I 2nd that nomination- such a throttling song.

Apr 23 12 - 8:29am
BrosephofArimathea

Almost Lover by A Fine Frenzy. So many Youtube covers.

Apr 23 12 - 10:15am
cs

I don't know why she isn't huge. Great voice and great songwriting.

Apr 23 12 - 12:33pm
For serious

She was incredible.

Apr 23 12 - 7:00pm
Danny

You literally took the words right out of my mouth! Such an amazingly beautiful song.

Apr 23 12 - 9:49am
Ted

First song I thought of was Hopeless by the Wrens.

Apr 23 12 - 1:13pm
On that note

"Miss Me" totally crushes it, too.

Apr 23 12 - 1:52pm
loue

"She Sends Kisses" is what I thought of.

Apr 23 12 - 10:44am
aasAA

Bob dylan- Standing in the doorway
Damien Rice- Rootless tree (fuck youuuuuu)
good woman- Cat Power

Apr 24 12 - 1:47am
PP

YES on Rootless Tree. That songs gives me chills.
"Let me out 'cause it's hell in your arms."

Apr 24 12 - 11:06am
M

Yes. Damien should be in this list. Even his lovesongs feel like breakup songs!

Apr 23 12 - 10:57am
mp

Personally, I would have included Postal Service's Nothing Better, and Stars' Your Ex-Lover Is Dead both in the top 5

Apr 24 12 - 1:49am
PP

All of that time you thought I was sad, I was trying to remember your name.

Apr 26 12 - 4:12pm
allaboutgeorge

I'm not sorry I met you
I'm not sorry it's over
I'm not sorry there's nothing to save

Apr 23 12 - 11:29am
tn

My personal fave: Goldfrapp's "Rocket". Strap that bastard down & light it up! Hilarious video.

Apr 23 12 - 11:41am
Jinna

Wow, I'm old or something. I could barely relate to this one.

Apr 23 12 - 12:16pm
Mary

Burn by usher didn't make it?! Dude! That song got so much airplay, and for the first 50 times it was still pretty sad

Apr 23 12 - 1:11pm
jonathan

Amy Winehouse, "Tears Dry On Their Own" Should have been Number One!

Apr 23 12 - 1:46pm
phil

AMEN

Apr 23 12 - 1:41pm
Z

Elliot Smith's 'somebody that I used to know' off the Figure 8 album...

http://www.youtube.com/watch?v=F_FpORpi5l0

Apr 23 12 - 1:54pm
huh

For Justin Timberlake, I really love "What goes around, come around", especially the live versions. Cry Me A River seems like kicking someone with a mental illness when she's down. Also, it's a little too deliberately ridicule for my taste. What Goes Around is angry and wallowing, just the way I like my breakup music.

Apr 23 12 - 3:32pm
Tyler Too

Overall, a great list, and a great exercise in nostalgia reading through it. I probably would have included some combination of these songs, though:

Robyn / Be Mine
Bat for Lashes / Daniel
Bat for Lashes / Sad Eyes
Radiohead / There There
Ani Difranco / Soft Shoulder

Apr 23 12 - 5:49pm
bring the bitter

Shellac's "Prayer to God" - now THAT'S catharsis. Maybe it doesn't count because it's post-breakup and best for when you see the ex with someone new?

Apr 26 12 - 9:27pm
mk

word

Apr 23 12 - 11:19pm
Alejandra

WHERE THE HECK IS GOTYE'S SOMEBODY THAT I USED TO KNOW?!

Apr 24 12 - 12:05am
random

I forget - which year in the 2000s was that released again?

Apr 24 12 - 1:22am
:)

Did everyone block "Beautiful" by James Blunt from their memories? Or is it not break up-y enough?

Apr 24 12 - 10:20am
Alex Heigl

No, we blocked it from our memories.

Apr 24 12 - 2:42pm
:)

I figured. I was in beauty school when it came out, we played it so many times it will never be forgotten :(

Apr 24 12 - 1:50am
PP

Beck's "Sea Change" is the most heartwrenching whole album about a break-up.

Apr 24 12 - 11:10am
M

The list is generally OK but I really, really disagree with the inclusion of that Lady Gaga song. It's just awful.

Apr 24 12 - 2:02pm
lt

So long as you do have a rilo kiley song, breakin' up would have been a great choice, too

Apr 24 12 - 2:27pm
JKS

I love this list- too old and unhip to recognize many of these (your 80s list was the soundtrack to my teenage heartbreak) but am totally enjoying listening to them for the first time. Hope I won't have to compile them for any future heartbreak! Enjoyed the writeups and commentary, too- thank you.

Apr 24 12 - 3:43pm
emmahope

is this a sick joke??? where the hell is the all time break up girl power classic, Leave (Get Out) by teen senstation JoJo? Rectify this immediately!

Apr 24 12 - 8:17pm
sally

haha! that just made my day.

Apr 25 12 - 12:33pm
beth

the mountain goats? pretty much anything off of "get lonely" is perfect

http://www.youtube.com/watch?v=1bSdRizGYb0&ob=av3e

"the first time that i made coffee for just myself, i made too much of it/ but i drank it all, just because you hate it when i let things go to waste."

Apr 28 12 - 4:50am
Bruno

I'd prefer "Your Belgian Things," from We Shall All Be Healed. I am always crushed by "I wish you had a number where you are; it's hard with no one here to help me through it."

Apr 25 12 - 5:45pm
CC

I don't think Someone Great is a breakup song, really; it always seemed to me like it was about death. I Can Change might have been a better choice (although even that is more like a "pre-breakup" song, anyway.)

Apr 26 12 - 3:32am
huh

john mayers "gravity" or "im gonna find another you"?

Apr 26 12 - 4:41pm
Simon Billenness

What about "Maps" by the Yeah Yeah Yeah's with its wonderfully passive aggressive: "She won't love you like I loved you."

Apr 27 12 - 10:52am
Alex Heigl

It's actually "They don't love you like I love you," and it's a plea from Karen O to her musician boyfriend to not go on tour. It's more of a love song than a breakup song. Which is why we put it on our Greatest Love Songs of the 2000s list.

Apr 26 12 - 9:48pm
mk

mariah carey's "we belong together". pretty honest for a major pop song...

"i can't sleep at night when you are on my mind,
bobby womack's on the radio
saying to me "if you think you're lonely now"
wait a minute, this is too deep
so i turn the dial trying to catch a break
and then i hear Babyface,
I only think of you
and it's breaking my heart,
I try to hold it together,
but I'm falling apart"

We've all been there.

Apr 27 12 - 12:09pm
graham

While these lists tend to stay clear from the harder music genres, I have to point out that the title track from Converge's Jane Doe (2001) is the most intense break-up song ever, capping off the most intense break-up record ever.

http://www.youtube.com/watch?v=3YR9Bspqbps

Apr 27 12 - 2:45pm
Sassafras

The Spill Canvas...take your pick of their catalog of emo angst, although All Hail the Heartbreaker is the breakup song I return to time and time again. Also Bound to Happen, Polygraph Right Now, and All Over You are great as well.

Apr 27 12 - 10:04pm
Bloop

where's Frightened Rabbit? Especially Backwards Walk!

Apr 28 12 - 4:55am
Bruno

That whole album is brutal. I might prefer "Good Arms vs Bad Arms" or "Keep Yourself Warm," but yeah, they should be here.

May 04 12 - 9:11am
JfnB

I love that you turned this into a spotify playlist

Jul 26 12 - 8:54pm
willclarksonic

For me Kelly Clarkson has the top she always has the best break up songs in the business, Behind these hazel eyes, because of you, already gone and STRONGER are incredible examples of it, this last song is a huge hit of 2012 and one of er best songs ever. Luv her.