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The Top 100 Breakup Songs of All Time (First Draft)

Thu, Jul 2, 2009

Pop Culture

This is the first of a series of posts we’ll be doing on the best breakup songs of all time. The below 100 was originally published in our book BUH BYE: The Ultimate Guide to Dumping and Being Dumped (which was called “hilarious and fantastic” by our one Amazon reviewer). Naturally, we like the list, but want to know which essential songs you think are missing, and which, if any, you would definitely not include. Unleash your wrath in the comments section.

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; the Bridget Jones version works, but only with the visual)
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” – 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” – Henry 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

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99 Responses to “The Top 100 Breakup Songs of All Time (First Draft)”

  1. AnotherNicole Says:

    So many good songs already on the list!
    But, I gotta go with…
    “Alone” and “It Hurt So Bad”- Susan Tedeschi

    There are SO many from Otis Redding: “Pain in My Heart”, “Nobody Knows You When You’re Down and Out”, “I’ve Got Dreams to Remember”, “Just One More Day”, “I Love You More Than Words Can Say”

    Oh, & don’t forget Cake’s version of “I Will Survive”.

    The rest of an eclectic list:
    “Who Will Comfort Me”, “Your Heart Is Black As Night”, and “Gone” – Melody Gardot
    “Here without you” – 3 Doors Down
    “Lost” – Michael Buble
    “You Don’t Love Me” and “Don’t Go” – Matthew Sweet
    “Nothing Ever Hurt Like You”, “If You Don’t Wanna Love Me”, and “The Last Goodbye” – James Morrison
    “Last Request” and “Rewind” – Paolo Nutini

    80′s/90′s style:
    “Separate Ways (Worlds Apart)”, “I’ll Be Alright Without You,” “Ask the Lonely” – Journey
    “Who’s Lovin’ You” – Terence Trent d’Arby
    “Kiss Off” – Violent Femmes

    R&B style:
    “One Last Cry” – Brian McKnight
    “Un-break My Heart”, “Love Shoulda Brought You Home”, “How Could An Angel Break My Heart”, and “Breathe Again” – Toni Braxton

  2. alison Says:

    “Say it Ain’t So” – Weezer

  3. Sooter Says:

    Ne Me Quitte Pas – Nina Simone

  4. Craig Says:

    Innumerable Magnetic Fields songs, including but not limited to
    “All My Little Words”
    “I don’t want to get over you”
    “busby berkely dreams” (for the mopier moments)

    Also “People Ain’t no good” by Nick Cave and the Bad Seeds.

  5. tracey Says:

    Elliott Smith – “Say Yes”

    George Michael – Waiting For that Day/You Can’t Always Get What You Want”

  6. karen hunter Says:

    Jewel – You Were Meant For Me

  7. Jay Jay Says:

    It aint me babe – bob dylan

  8. Epiphany Says:

    Bob Dylan – “Don’t Think Twice”

  9. Dave W Says:

    “I Can’t Make You Love Me” – Bonnie Raitt
    “Already Gone” – The Eagles
    “Till Death Do Us Part” – Madonna
    “Cry Me A River” – Justin Timberlake
    “Bye Bye Love” – Everly Brothers
    “Donna” – Ritchie Valens
    “I Will Always Love You” – Dolly Parton
    “Big Girls Don’t Cry” – Fergie
    “Leave(Get Out)” – Jojo
    “Your Time is Gonna Come” and
    “Babe I’m Gonna Leave You” – Led Zeppelin
    “Still Ain’t Over You” – Augustana(live on Letterman pref’d)
    “Hemorrhage(in my hands)” – Fuel
    “Yesterday”??? – The Beatles

  10. Courtney Says:

    SO HAPPY to see Your Ex-Lover is Dead by Stars on this list!!! Wonderful song, perfect for getting over a breakup.

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


  11. Slartibartfast Says:

    There are already some fantastic suggestions, but I’d like to submit the following for consideration:
    “Diary”- Bread
    “The Last Day of Our Acquaintance”- Sinead O’Connor
    “Tuesday’s Gone”- Lynyrd Skynyrd
    “Breathe (2AM)”- Anna Nalick
    “Cumbersome”- 7 Mary 3
    “Valse Bebe”- Beausoleil
    “If You Could Read My Mind”- Gordon Lightfoot

  12. David Says:

    Bob Dylan’s entire album “Blood on the Tracks”, probably the best breakup album of all time. Depending on your mood, “Idiot Wind” (angry, self-righteous), “You’re Gonna Make Me Lonesome When You Go” (wistful), “If You See Her, Say Hello” (resigned), “You’re A Big Girl Now” (like a corkscrew to my heart)… or the masterpiece opening track, “Tangled Up In Blue” (contemplative).

    The Wallflowers’ Jakob Dylan said of this album “The songs are my parents talking.” And no, they didn’t stay together.

  13. Kristin Says:

    Props for mentioning Jeff Buckley. I could put the songs you listed on repeat and that’s enough for a tear fest.

    A couple of others:

    Paper Bag- Fiona Apple
    Nicest Thing – Kate Nash
    House of Cards- Radiohead

    Those three above are more unrequited love songs, but still.

    Walk Away – Ben Harper
    I’m Gonna Find Another You – John Mayer
    How’s the World Treating You?- James Taylor & Alison Krauss
    Sleep to Dream – Fiona Apple
    Wreck of the Day – Anna Malick

    And throwing in a bit of country cause I can…

    Songs About Rain & Smoke Rings in the Dark – Gary Allen
    Kerosene – Miranda Lambert

  14. AlanK Says:

    It’s worth pointing out that music did not begin with Elvis. Cole Porter, anyone? Sondheim? About half of all of Sinatra’s stuff?

    But anyway,,,you can’t do better than Dylan”s “It ain’t me babe,” as mentioned before. And almost all of Leonard Cohen’s songs are nasty, with “Everybody knows” perhaps the king. (“They’ll be a meter round your bed” indeed.)

  15. trillie Says:

    #1 in my list: Nine Inch Nails: “Something I Can Never Have” (there’s a beautiful version on Youtube here: http://www.youtube.com/watch?v=UEW8riKU_tE – “Gray would be the color if I had a heart”, come on!)

  16. Slartibartfast Says:


    “Everybody Knows” is a brilliant suggestion! I couldn’t choose between Leonard’s recording or Concrete Blonde’s cover myself, but either one is spot-on in my book. And let’s not give short shrift to “Greensleeves” either. At least, it’s always been a favorite of mine.

  17. nicole Says:

    I Believe- Chris Issak

  18. Hannah Says:

    I’m really not a Death Cab fan, but I’d have to say that “Summer Skin” would fit pretty well on this list.

  19. Marian Says:

    Who Knew-Pink
    2 AM/ Breathe- Anna Nalick!! i cry every time.lol.

  20. kjb10 Says:

    “Walk Away” by Ben Harper- How could this not make this list???? I cry every time!

  21. Auni Says:

    I’m suprised “Gives you Hell” by the AAR… Especially when you find out that ex stole from the wrong cookie Jar… hehehe

  22. troy Says:

    “Boys of Summer” – Ataris over Don Henley

  23. Laura Says:

    He Stopped Loving Her Today – George Jones (I think)
    Surprised it wasn’t on the list!

  24. Raavynn Says:

    “Para Noir” by Marilyn Manson. The best angry break-up song EVER. It helps you feel vindicated after you’ve been used, abused, or neglected.

  25. rachie Says:

    Best I Ever Had – Vertical Horizon just listen to it and ull understand

  26. Ericabug Says:

    What about Roses From My Friends by Ben Harper since we’re mentioning him, or Mexico by Incubus, or a rarer one by them still, which is Monuments & Melodies

  27. Lars Petrus Says:

    “Time of Your Life” – Green Day

    That this breakup song is (or was) one of the most played at weddings makes it a supreme irony!

  28. Plucky Poultry Says:

    Lets see….”I Don’t Want You Back”-Emon (hilariously awesome, now that is one heated bloke)
    Fiona Apple: “Limp”
    Mary J Blige: “Ain’t really Love” & “Not Gonna Cry”
    Profyle: “Liar”
    Toni Braxton: “Another Sad Love Song”
    Changing Faces: “Ghettout”
    Chrisette Michele: “Best of Me” & “Epiphany”
    Ideal: “Get Gone”
    Beyonce: “Me, Myself & I” & “If I Were a Boy”
    Diana Krall: “Walk On By”
    Aaliyah: The One I Gave My Heart To
    Brandy: “Have You Ever?”
    Anthony Hamilton: “Can’t Let Go” (for those of us who can’t leave well enough alone)
    Avant: “Separated”

    Believe it or not, Snoop Dogg has a song called “Waste of Time,” I’m pretty sure we’ve all been here in one form or another. Who woulda thunk Snoop? May not like hip-hop, but the lyrics are pretty spot on in his owny Doggy way.

  29. Tritty Says:

    Great tunes here, so have some more
    “outta love”- Anastasia
    “pictures of you”- Cure
    “wicked game”- Chris Issak
    “goodbye to you”- Michelle Branch
    “what do i have to do” Stabbing Westward
    “the thing i hate”- Stabbing Westward
    “it’ll be alright” Ween
    “fighter”- Christina Agulaira (whats her face)

  30. Maxwell Says:

    “Don’t Speak” No Doubt
    “Kissing a Fool” George Michael

  31. Afifah Says:

    My list:

    Cher– Believe
    Cher– Strong Enough
    Destiny’s Child– Survivor
    Lara Fabian– I Will Love Again
    M People- Moving on Up
    Scandal– Goodbye to You
    Don’t Bother by Shakira
    Christina Aguilera– Fighter
    Gloria Gaynor– I Will Survive
    Nancy Sinatra– These Boots are Made For Walkin’
    Get Out (Leave) – JoJo
    Beyonce – Irreplacable
    Britney Spears – Stronger
    Daughtry – Over You
    Fireflight – Unbreakable
    Hilary Duff – So Yesterday
    JoJo – Leave (Get Out)
    Katharine McPhee – Over It
    Kelly Clarkson – Never Again
    Kelly Clarkson – Since U Been Gone
    Kristinia DeBarge – Goodbye
    Linkin Park – Don’t Stay
    Pink – So What
    Pussycat Dolls – I Don’t Need A Man
    September- Cry For You
    Stacy Orrico – I’m Not Missing You
    The All American Rejects – Gives You Hell

  32. phatbootycutie Says:

    First one that comes to mind is Debra cox along with the dude from that group called “Next”. It’s called “We can’t be friends”… I almost burst out into tears whenever I hear it. Really, a wonderful collaberation!

  33. Rick Says:

    So many possibilities…..

    D-I-V-O-R-C-E byTammy Wynette
    Tears Of A Clown by Smokey Robinson & The Miracles
    Walk Away Renee by The Left Banke
    You Don’t Bring Me Flowers by Barbra Streisand
    What Becomes of the Brokenhearted – The Temptations
    The Story In Your Eyes by Moody Blues

    Would love to see the lists combined & voted on…..

  34. Lydia Says:

    Any song by Fiona Apple is basically a good break up song, especially…

    “Won’t do no good to hold no seance/What’s gone is gone and you can’t bring it back around”

    Sick In My head
    “And the signature thing that used to bring a following I have trouble now even remembering”

    Get Him Back
    “Now every other man I see reminds me of the one man who disappoint me”

    Not About Love
    “This is not about love/’Cause I am not in love/In fact I can’t stop falling out”

    Yeah – she’s my favorite angry chick

  35. Kate Says:

    what about “Hit ‘Em Up Style” by Blu Cantrell

  36. Pinktitties Says:

    Don’t fear the reaper – blue oyster cult
    Street fighting man – the stones
    Champagne and reefer – muddy waters
    Tnt – ac/dc
    Imagine – john lennon

  37. woodward Says:

    many excellent suggestions on here, but wanted to include:
    “Its Too Late” by Carole King and
    “Traces of Love” by the Classics IV

  38. Kep Says:

    Daughtry – NO SURPRISE

    Straight to the point and layin it out on the line! Can’t put a quote without putting the whole song on here. But here is the link to the video, which I feel could have been better but hey, it still doesn’t take away from the lyrics.

  39. Giz17 Says:

    “Our Song” – Aventura
    “Losing My Religion” – R.E.M.
    “My Immortal” – Evanessene
    Just a few I thought should be added

  40. tyler Says:

    Let’s just kiss and say goodbye by the Manhattans

  41. jo Says:

    Like A Drug – Queens of The Stone Age (Desert Sessions version)

    Here I Go Again – Whitesnake

  42. Madamoiselle L Says:

    Two songs by the Beatles are the all time best break up songs.


    For No One

    (The day breaks, your mind aches, you find that all her words of kindness linger on…..when she no longer needs you……and in your mind you see nothing, no trace of love behind the tears…..shed……for No One….a Love which should have lasted years)

    Second place

    John Lennon’s


    Jealous Guy

  43. mk Says:

    Seconding “Don’t Think Twice,” the cover by Joan Baez + The Indigo Girls is the best.

    Also on my playlist:
    Untouchable Face – Ani DiFranco
    Won’t Be Home – Old 97s
    Wish the Worst – Old 97s
    Bust Your Windows – Jazmine Sullivan (or … Glee)
    Love is Just A Four Letter Word – also Bobby D, I think? But Joan does it best
    There You Go – P!nk
    Ring The Alarm – Beyonce
    … and others that have been listed already. I’m really all about the righteous indignation, I guess.

  44. Gabbi Says:

    My favorites lately have been:

    “No Children,” the Mountain Goats
    “I’ll Miss You,” Ween
    “Sunshine,” Handsome Boy Modeling School
    “You Were My Fiji,” John Vanderslice

    Jeff Buckley is always good but I like to keep some healthy bitterness in there.

  45. ANC Says:

    Go ahead…alicia keys

  46. Hala Says:

    how do you keep love alive -ryan adams

  47. Boopboopbeedoop Says:

    Aimee Mann – That’s Just What You Are.
    It’s bitter without leaving a bad taste.

  48. Boopboopbeedoop Says:

    Oh! And Liz Phair – Ant In Alaska

  49. Jasmine Says:

    Don’t Cry – GunsN’ Roses
    Babe I’m Gonna Leave You – Led Zepplin
    Painted On My Heart – The Cult
    Angel – Amanda Perez
    Something To Lose – Nadia Ali
    Apologise – One Republic
    Hole In The Head – Sugababes
    Right Here Waiting – Staind
    What Hurts The Most – Rascal Flatts
    He Wasn’t Man Enough – Toni Braxton
    Just Feel Better – Steven Tyler Ft. Santana
    9 Crimes – Damien Rice
    Moving Mountains – Usher
    Won’t Go Home Without You – Maroon 5
    Stop – Sam Brown
    Rain On Me – Ashanti
    Heartless – Kanye West
    Heel Over Head – Puddle Of Mudd
    Away From Me – Puddle Of Mudd
    Sick & Tired – Anastacia
    Pieces of A Dream – Anastacia
    It Must Have Been Love – Roxette
    Under The Thumb – Amy Studt
    Stuck – Stacie Orrico
    Nobody Knows It But Me – The Tony Rich Project
    Kiss – Korn
    Over – Lindsay Lohan
    She Fucking Hates Me – Puddle Of Mudd
    Supergirl – Reamon
    Always – Bon Jovi
    Cry Baby Cry – Sean Paul, Joss Stone, Santana

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