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

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


  1. Literally every Taylor swift song ever. Honestly most pop songs are break up songs

  2. Blower’s Daughter – Damian Rice
    A Woman in His arms – Linda Eder
    Sour times – Portishead
    Cry me a river – Julie London
    Don’t stop now – Emmy Rossum
    Between the Lines – Sara Bareillis
    Passive – A Perfect Circle
    I know his so well – Elaine Paige
    Tear in your hand – Tori Amos
    In Between Shades- Jill Tracy
    Pofig – In Yan
    Sleeps with Butterflies – Tori Amos
    My give a damn’s busted – Jodee Messina
    Where Shadows fall – Jill Tracy

  3. Umm, No one has mentioned Mary J. Blidge, she has so many soulful breakup songs…
    some of my favorites:
    – not gon cry
    – I’m going down
    – be without you
    – Mr. Wrong
    – Why
    – I can love you
    – Take me as I am
    – Enough Crying
    – Missing you
    and how about Whitney Houston?
    _ I will always love you
    – Heartbreak Hotel
    – I have nothing
    – Where do broken hearts go
    – It’s not right but it’s okay

    I’m sure there are many others, but I can’t think of them off the top of my head. I always turn to Whitney and Mary when I have heartache.

  4. i just want to personally say to all of you that have gone through a break up that my heart goes out to you. i recently experenced a terrible break up. he was the best friend i have ever had. we broke up 3 weeks before our 2 year anniversary. i cant seem to keep the tears from falling or my heart from breaking. he’s the one i want to hate the most but the one i need as well. this is the worst emotional pain i have ever felt. just know that i know what you are going through and please just know that no matter what happened you are an amazing person. and i wish you all the best in your journeys through these break ups<3
    these songs have helped me a ton..i hope they help you too.

    beyonce-broken hearted girl
    i cant make you love me-tank
    wide awake-katy perry
    go on girl-ne-yo
    boy without a hear-jojo
    catch me-demi lovato
    love that lets go-miley cyrus/hannah montana
    final goodbye-rihanna
    a million miles away-rihanna
    fix a hear-demi lovato
    hate u-mariah carey
    i remember-keyshia cole
    i wish-one direction
    marvins room-drake
    rumour has it-adele
    take a bow-rihanna
    taken-one direction
    that should be me-justin bieber
    thinking about you-frank ocean
    up-justin bieber

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