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MSNBC's article "In Time for Valentine's Day: Best Breakup Songs" lists what we would actually consider the five WORST songs about heartache ever:

1. "And I Am Telling You I Am Not Going" from Dreamgirls. This painfully long-ass melodramatic song made us want to break up with that movie. The only version we can half-stomach is by that pasty white kid on The View.

2. "Ain't Too Proud to Beg" by the Temptations. Do you know anyone who'd want to put this peppy song on after they caught the love of their life doing it with their best friend? Besides your grandpa? Us neither.

3. "Go Your Own Way" by Fleetwood Mac. With its foot-tapping, tamborine-hip-slapping beat, the lyrics might as well be "You can throw a soiree, make a bouquet, you can call it another happy day." 

4. "Without You" by Harry Nilsson. Okay, this is actually a really good one, but "worst breakup songs ever except one" didn't make as catchy a headline. 

5. "You're Gonna Make Me Lonesome When You Go" by Bob Dylan. Dylan's without a doubt a folk legend who changed the course of popular music and whose lyrics can't be beat, but can we all just admit that his voice sounds like Montgomery Burns after a hit of helium? If you gotta go with a Dylan song about love lost, the slower and softer "Girl From the North Country" is your best bet. 

We could come up with about 100 songs that are better breakup songs. In fact, we did, in our book "Buh Bye: The Ultimate Guide to Dumping and Getting Dumped." Read our list after the jump and see if you agree, disagree or have any others that should have made the cut. We only wish we'd heard "The Three of Us" on This American Life before our book deadline. 

The Top 100 Breakup Songs of All Time:

1 "50 Ways to Leave Your Lover" - Paul Simon
2 "Absolutely Zero" - Jason Mraz
3 "Against All Odds" - Phil Collins or The Postal Service version
4 "All Alone Am I" - Brenda Lee
5 "All By Myself" - Eric Carmen (definitely not the Celine Dion version)
6 "All My Ex's Live in Texas" - George Strait
7 "Alone Again (Naturally)" - Gilbert O'Sullivan
8 "Another Lonely Day" - Ben Harper
9 "Apart" - The Cure
10 "Are You Lonesome Tonight" - Elvis Presley
11 "Ballad of Big Nothing" - Elliott Smith
12 "Black" - Pearl Jam
13 "Blackout" - Muse
14 "Blue Moon Revisited" - Cowboy Junkies
15 "Can't Stand Losing You" - The Police
16 "Careless Whisper" - Wham!
17 "Crazy" - Patsy Cline or Willie Nelson
18 "Crown of Love" - Arcade Fire
19 "Crying" - Roy Orbison
20 "Don't Cry Out Loud" - Melissa Manchester
21 "Don't Leave Me This Way" - Thelma Houston
22 "Don't Walk Away" - ELO
23 "Don't You Want Me" - The Human League
24 "Ever Fallen in Love" - The Buzzcocks
25 "Every Breath You Take" - The Police
26 "Everybody Hurts" - R.E.M.
27 "Everyday I Love You Less and Less" - Kaiser Chiefs
28 "Ex-Factor" - Lauren Hill 
29 "Ex-Girlfriend" - No Doubt
30 "Girl from the North Country" - Bob Dylan
31 "Girl" - Beatles
32 "Grace Cathedral Hill" - The Decemberists
33 "Harden My Heart" - QuarterFlash
34 "Heartbreak Hotel" - Elvis Presley
35 "Heartbreaker" - Pat Benatar 
36 "Hopelessly Devoted to You" - Olivia Newton John (Grease Soundtrack)
37 "How Can You Be Sure?" - Radiohead
38 "I Fall to Pieces" - Patsy Cline
39 "I Hope You're Happy Now" - Elvis Costello
40 "I Never Cared for You" - Willie Nelson
41 "I Used to Love Her" - Guns n' Roses
42 "I Want You" - Elvis Costello
43 "I Will Survive" - Gloria Gaynor
44 "If I Can't Have You" - Yvonne Ellimen
45 "I'm So Lonesome I Could Cry" - Take your pick: Hank Williams, Elvis Presley, Cowboy Junkies, or Johnny Cash
46 "I'm Sorry" - Brenda Lee
47 "It's a Heartache" - Juice Newton or Bonnie Tyler
48 "It's Not Right, But It's Okay" - Whitney Houston (the Thunderpuss remix)
49 "It's Over" - Roy Orbison
50 "I've Been Loving You Too Long" - Otis Redding
51 "Killing Me Softly with His Song" - Fugees over Roberta Flack
52 "Last Goodbye" - Jeff Buckley
53 "Leavin' on Your Mind" - Patsy Cline
54 "Lilac Wine" - Jeff Buckley
55 "Lonesome Tears" - Beck
56 "Lost Cause" - Beck
57 "Love Hurts" - Nazareth (the cover by Joan Jett will do in a pinch)
58 "Love is Stronger Than Death" - The The
59 "Love on the Rocks" - Neil Diamond
60 "Love Stinks" - J. Geils Band
61 "Love Will Tear Us Apart" - Joy Division
62 "Lover, You Should Have Come Over" - Jeff Buckley
63 "Lush Life" - Billy Strayhorn
64 "Mandy" - Barry Manilow
65 "No More Tears (Enough Is Enough)" - Barbra Streisand & Donna Summer
66 "Nothing Compares to You 2 U" - Sinead O'Connor or Prince
67 "One" - Aimee Mann (Magnolia soundtrack)
68 "Ordinary World" - Duran Duran
69 "Run" - Snow Patrol
70 "Separate Ways" - Journey
71 "She Is Gone" - Willie Nelson
72 "She's Got You" - Patsy Cline
73 "Should've Been in Love" - Wilco
74 "Since I Don't Have You" - Guns N' Roses version
75 "Since U Been Gone" - Kelly Clarkson
76 "So Lonely" - The Police
77 "So Wrong" - Patsy Cline
78 "Soma" - Smashing Pumpkins
79 "Somebody That I Used to Know" - Elliott Smith
80 "Strange" - Patsy Cline
81 "Sweet Dreams" - Patsy Cline
82 "Tainted Love" - Soft Cell
83 "The Seventh Stranger" - Duran Duran
84 "The Sign" - Ace of Base
85 "There's a Tear in My Beer" - Hank Williams
86 "These Arms of Mine" - Otis Redding
87 "This Woman's Work" - Kate Bush
88 "Total Eclipse of the Heart" - Bonnie Tyler
89 "True Happiness This Way Lies" - The The
90 "Two Out of Three Ain't Bad" - Meatloaf
91 "We Belong " - Pat Benatar
92 "Why Can't He Be You" - Patsy Cline
93 "Without You" - Harry Nilsson (not the Mariah Carey version)
94 "Writing to Reach You" - Travis
95 "You Give Love a Bad Name" - Bon Jovi
96 "You Oughta Know" - Alanis Morissette
97 "You'll Never Find Another Love Like Mine" - Lou Rawls
98 "Your Ex-Lover is Dead" - Stars
99 "You're Not the Girl You Think You Are" - Crowded House
100 "You've Lost That Loving Feeling" - Righteous Brothers


7 Comments

tracey said:

Back in 1991 at the tender age of 19 after my first love broke up with me, I cried my eyes out to George Michael's "Waiting for that Day/You Can't Always Get What You Want": "But something I just can't explain, something in me needs this pain/I know I'll never see your face again" and "Now everybody's talking about this new decade/Like you say the magic numbers then just say goodbye to the stupid mistakes you made/Oh my memory/Serves me far too well."

In 2003 after a much more minor breakup, thankfully, I discovered Elliot Smith's "Say Yes: "She'll decide what she wants/I'll probably be the last to know/No one says until it shows/See how it is/They want you or they don't/Say yes."

Also...The's The's "August & September": "I knew what you were doing/And I knew what you'd done/You're life with me was ending/Your new life had begun."

Sinead O'Connor's "The Last Day of our Acquaintance"

I could probably go on and on...

Natascha said:

I second the Sinead O'Connor suggestion from the first comment.

But how could you forget Lloyd Cole & the Commotions "Heartbroken"? My first love included that in a mixed tape for me. Sure made his point....

Sophie said:

I agree with you about Dylan's voice, but there is a magnificent version of "You're Gonna Make Me Lonesome When You Go" by Madeleine Peyroux that may reconcile you with the song.

becky said:

"The Last Thing I Needed, First Thing This Morning" by Willie Nelson. And I am NOT a country music fan.

naomi said:

Oh, 'halleluja', the Jeff Buckley version. Saddest song in the world.

Melissa said:

Totally disagree on the Dylan thing--I actually put "You're Gonna Make Me Lonesome When You Go" on my one and only breakup mix, which ended up being one of my best mix CDs ever. And Montgomery Burns after a hit of helium? Them's fightin' words, ladies.

I have this whole theory that every break up has its own break-up song from Blood on the Tracks, and that you know the relationship's over the exact moment you figure out which song is that relationship's breakup song. It works, really.

I also like "Waltz #2" instead of "Ballad of Big Nothing" as my Elliott Smith representation: "Here it is, the revenge to a tune--you're no good..." The man knows depression. As does Conor Oberst, whose "Lover I Don't Have to Love" goes on my list.

Rick said:

You must be joking - you don't include Nillson's "You're Breaking My Heart" ?

You're breaking my heart
You're tearing it apart
So fuck you

Priceless.
Awesome website, by the way. Just discovered it this evening. Keep up the great work.

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