1. Gloria Gaynor, “I Will Survive”

Did you think this song would crumble? Did you think it’d just lay down and die? Oh no! “I Will Survive” by Gloria Gaynoris such a classic that it’s actually referenced in breakup songs by Mariah Carey (“Breakdown”) and Dua Lipa (“Don’t Start Now”). Gaynor told NPR of “I Will Survive” in 2019, “It’s the core of my purpose. It really is. I—for a long time, I felt that it was kind of a double-edged sword, maybe even a—kind of an albatross around my neck. And people weren’t recognizing that I did other songs, that I had other great songs. And, you know, I just didn’t really like the idea that it was the only popular song in my repertoire. But now I’ve come to understand that it is the core of my purpose, and I’m very, very happy with it. It is still the song that I like to sing most in my shows—except for ‘Amazing Grace’ now. But yeah, the song has done so much for so many people, and I am pleased and proud to have been the one to record it.” https://www.youtube.com/watch?v=ARt9HV9T0w8

2. Carly Simon, “You’re So Vain”

To this day, no one is quite sure who wore the mysterious apricot scarf Carly Simon sings of in “You’re So Vain,” but she did mention in Janet Jackson’s song “Son of a Gun” that it wasn’t Mick Jagger. https://www.youtube.com/watch?v=mQZmCJUSC6g

3. Alanis Morissette, “You Oughta Know”

Now this is a breakup song. Alanis Morissette owned all of our rage at two-timing exes with “You Oughta Know,” propelling her debut album on Maverick Records (her third album overall) Jagged Little Pill to shatter records worldwide, as well as to shatter a huge chunk of the glass ceiling for women in rock. Fun fact? She recorded the song in one take.

4. Fleetwood Mac, “Go Your Own Way”

Talk about savage: Lindsey Buckinghamwrote “Go Your Own Way” about his split from Fleetwood Mac bandmate Stevie Nicks…and then they had to perform it together for years.

5. Kelly Clarkson, “Since U Been Gone”

Kelly Clarksonhas several breakup anthems under her belt, including “Stronger (What Doesn’t Kill You)” (her first No. 1) and “Never Again,” but it’s her 2004 classic “Since U Been Gone” that inspires every brassy, brokenhearted belter at karaoke.

6. The Beatles, “Yesterday”

This Beatles classic is as heartbreaking as it is simple and beautiful. https://www.youtube.com/watch?v=wXTJBr9tt8Q

7. Bonnie Raitt, “I Can’t Make You Love Me”

Bonnie Raitt makes us all misty with this tune about unrequited love that is all too relatable. https://www.youtube.com/watch?v=nW9Cu6GYqxo

8. Big Brother and the Holding Company, “Piece of My Heart”

Janis Joplin’s vocals convey her struggle with showing that “a woman can be tough” while also having one heck of a broken heart. https://www.youtube.com/watch?v=AxXg4Irb6yE

9. Dolly Parton, “I Will Always Love You”

Whitney Houston made this song mega-famous in The Bodyguard, but Dolly Parton ’s vocals perfectly conveyed in her 1974 original version that this is actually a super-sad breakup song. https://www.youtube.com/watch?v=aDqqm_gTPjc

10. Whitney Houston, “I Will Always Love You”

While Parton had the original and sadder rendition, Houston made “I Will Always Love You” iconic with her inimitable vocals. The cover, from The Bodyguard soundtrack, won two Grammys and is the bestselling single by a woman in history.

11. Phil Collins, “Against All Odds”

Phil Collins is all of us begging for a second chance with a lover who left in this 1981 classic. Mariah Carey delivered a worthy cover of it on her Rainbow album in 1999. https://www.youtube.com/watch?v=CkGg1bzfSys

12. Beyoncé, “Irreplaceable”

Beyoncé makes it clear: She can have another you in a minute. The song became B’Day’s most successful single and topped the Billboard Hot 100 chart for ten straight weeks. Interestingly, the song almost was very different: When Ne-Yowrote the track, he had Faith Hillor Shania Twainin mind to sell it as a country song.

13. Carrie Underwood, “Before He Cheats”

Listen, vandalism is a crime. It’s bad. You shouldn’t do it. But Carrie Underwood, like us, 100 percent understands the temptation. https://www.youtube.com/watch?v=WaSy8yy-mr8

14. Marvin Gaye, “Heard It Through the Grapevine”

This Marvin Gaye classic (a cover of a song previously released by The Miracles, then by Gladys Knight and the Pips) is a testament to the damage that gossip can do to relationships and feelings. If you’re gonna dump the poor guy, tell him before you tell everyone else! https://www.youtube.com/watch?v=Y7dGdrP3pms

15. Ella Fitzgerald, “Cry Me a River”

Songwriter Arthur Hamilton penned “Cry Me a River” specifically for Ella Fitzgerald. Though she wasn’t the first artist to record it, she was indisputably the best.

16. Bob Dylan, “Don’t Think Twice, It’s All Right”

When Bob Dylan sings this kiss-off to a lousy ex, it sounds resigned, a little condescending and lighthearted. The lyrics work so well, though, that when Keshacovered it, the song transformed into something absolutely devastating. https://www.youtube.com/watch?v=1iHhWh9FtsQ

17. Madonna, “Take a Bow”

Madonnasays goodbye to a lover who’s playing a role, not actually adoring her, in this 1994 ballad—co-produced by Babyface and backed by a full orchestra and live strings—from Bedtime Stories.

18. Mariah Carey, “We Belong Together”

Carey basically wrote an anthem for the denial phase of a breakup with “We Belong Together,” featuring lyrics “When you left I lost a part of me / It’s still so hard to believe.” The song, which also references Bobby Lomack’s “If You Think You’re Lonely Now” and TheDeele and Babyface’s “Two Occasions,” also served as Carey’s comeback single in 2005, shattering chart records and becoming her 16th No. 1 hit. The track tied with Carey’s own “One Sweet Day” as the third longest-running No. 1 hit in history, and Billboard named it the Song of the Decade. It remains one of the biggest-selling songs of all time.

19. Prince, “Purple Rain”

This signature Prince power ballad has everything: Wistful lyrics, an insane guitar solo and that falsetto. https://www.youtube.com/watch?v=ryT-ltTDCko

20. Sinead O’Connor, “Nothing Compares 2 U”

This Prince-penned tune became Sinead O’Connor’s biggest hit. https://www.youtube.com/watch?v=0-EF60neguk

21. Elton John, “I’m Still Standing”

Elton John refuses to break down just because he’s breaking up, and his legendary sass is on full display with lines like, “And if love was a circus / You’d be a clown by now.” https://www.youtube.com/watch?v=ZHwVBirqD2s

22. Al Green, “How Can You Mend a Broken Heart”

Most famous for “Let’s Stay Together,” Al Green also slays it on songs about doing the opposite of that. https://www.youtube.com/watch?v=PTY6Kv0nPr8

23. Bill Withers, “Ain’t No Sunshine”

Late Bill Withers’ lament on a young lady who simply can’t stick around is as timeless as it is relatable. It was a breakthrough hit for Withers in 1971 and enjoyed a resurgence on the charts in 2009 after Kris Allencovered the song on American Idol.

24. Boyz II Men, “End of the Road”

The harmonies in “End of the Road” by Boyz II Men are so beautiful that they almost make up for the tears you’ll shed listening to this. https://www.youtube.com/watch?v=zDKO6XYXioc

25. Rod Stewart, “Maggie May”

Rod Stewart is trapped in a toxic romance with a cougar in “Maggie May,” but he can’t seem to break free—after insulting her and threatening to leave for half the song and going through pros and cons, he resigns himself: “I couldn’t leave you if I tried.” https://www.youtube.com/watch?v=EOl7dh7a-6g

26. Cher, “Believe”

Because there is life after love, and you will indeed get through this!

27. Mary J. Blige, “I’m Goin’ Down”

There is no singer more emotive than Mary J. Blige in “I’m Goin’ Down.” The song is actually a cover: Penned by Norman Whitfield, who worked with Motown Records in the ’60s, “I’m Goin’ Down” was first performed by Rose Royce for the Car Wash soundtrack in 1976.

28. Nancy Sinatra, “These Boots Are Made for Walkin’”

Nancy Sinatra was not here for a no-good two-timing cheat. https://www.youtube.com/watch?v=SbyAZQ45uww

29. Amy Winehouse, “Love Is a Losing Game”

Though “Back to Black” is more famous, “Love Is a Losing Game” is an even more heartbreaking tune from the late Amy Winehouse because of its inherent hopelessness about the seeming futility of romance since it never ends well. https://www.youtube.com/watch?v=nMO5Ko_77Hk

30. Roy Orbison, “Only the Lonely”

The late Roy Orbison sounds so lovelorn in this catchy tune that you just want to give him a hug. https://www.youtube.com/watch?v=kjq4wYuwgxs

31. Roxette, “It Must Have Been Love”

Roxette’s soaring ballad about resigning to a romance that’s over was originally released in 1987, but enjoyed a resurgence in popularity after being featured in Pretty Woman in 1990. https://www.youtube.com/watch?v=k2C5TjS2sh4

32. Adele, “Rolling in the Deep”

Adele can sing a brokenhearted power ballad like no one else, but honestly? We love her the most when she’s mad. https://www.youtube.com/watch?v=rYEDA3JcQqw

33. Carole King, “It’s Too Late”

There are few things more heartbreaking than a breakup of a relationship that both parties earnestly tried to save. Carole King nails the frustration, resignation and sadness that comes with knowing that it’s over, despite your and your partner’s best intentions. https://www.youtube.com/watch?v=VkKxmnrRVHo

34. John Mayer, “Slow Dancing In a Burning Room”

John Mayer croons of a romance that’s doomed and uses a pretty perfect metaphor for it. https://www.youtube.com/watch?v=32GZ3suxRn4

35. The Tony Rich Project, “Nobody Knows”

“Nobody Knows” by The Tony Rich Project perfectly captures the feeling of putting on a brave face in public while hiding your inner devastation over losing someone you love—and listing all the individual regrets you have about how it went wrong. https://www.youtube.com/watch?v=W7EyUY3-Wrg

36. Robyn, “Dancing On My Own”

“Dancing On My Own” by Robyn has such a great beat that it can almost seem less sad than it is—but her vocals sound as heartbreaking as the lyrics are. https://www.youtube.com/watch?v=CcNo07Xp8aQ

37. Taylor Swift, “All Too Well”

While Taylor Swift has made waves with singles like “We Are Never Ever Getting Back Together,” “Dear John” and “I Knew You Were Trouble,” one of her discography’s best tracks is this piano ballad from Red. “All Too Well” has the sort of storytelling usually relegated for country songs, and this Swifty fan favorite is a hallmark of Swift’s incredible, undeniable songwriting ability. https://www.youtube.com/watch?v=u7EexjQdT0s

38. John Lee Hooker, “Serves You Right to Suffer”

The title says it all about this blues classic: John Lee Hooker embraces karma’s treatment of a no-good ex, one of the best exercises in schadenfreude ever. https://www.youtube.com/watch?v=gJdHlra_fHA

39. Diana Ross and the Supremes, “Where Did Our Love Go?”

Diana Ross’ signature coo sounds profoundly sad on The Supremes’ “Where Did Our Love Go?,” a song about a man who loves the chase more than he loves his lady. https://www.youtube.com/watch?v=qTBmgAOO0Nw

40. Whitney Houston, “It’s Not Right, But It’s Okay”

Houston brings the receipts—literally—in “It’s Not Right, But It’s Okay,” a song about having documentation to back up your suspicions of a cheating man. The original is great, but there’s something so much more empowering about the Thunderpuss Remix. https://www.youtube.com/watch?v=gT2gHhfxYVc

41. Poison, “Every Rose Has Its Thorn”

Honestly, “Every Rose Has Its Thorn” makes us feel a lot less guilty about loving Rock Of Love. https://www.youtube.com/watch?v=j2r2nDhTzO4

42. Paul Simon, “50 Ways to Leave Your Lover”

Paul Simon wrote the handy “50 Ways to Leave Your Lover” as an amusing way to document his divorce from Peggy Harper. https://www.youtube.com/watch?v=ABXtWqmArUU

43. Joan Jett and the Blackhearts, “I Hate Myself for Loving You”

Joan Jett clearly didn’t realize she deserved a lot better in “I Hate Myself for Loving You,” but isn’t it somewhat comforting to know that even a rock goddess has been there? https://www.youtube.com/watch?v=bpNw7jYkbVc

44. Blu Cantrell, “Hit ‘Em Up Style”

Here’s hoping Mackenzie Bezos listened to Blu Cantrell’s “Hit ‘Em Up Style.” https://www.youtube.com/watch?v=LMOKlXfXn50

45. The Clash, “Should I Stay or Should I Go”

One of the catchiest and most melodic classic punk tunes is The Clash’s anthem about on-again-off-again love. https://www.youtube.com/watch?v=BN1WwnEDWAM

46. ABBA, “The Winner Takes It All”

Mamma mia, this one hurts! ABBA trades in their usual sunny pop for this heartwrenching ballad, featuring lyrics like, “You’ve come to shake my hand / I apologize / If it makes you feel bad / Seeing me so tense / No self-confidence / But you see / The winner takes it all.” https://www.youtube.com/watch?v=92cwKCU8Z5c

47. Elvis Presley, “Are You Lonesome Tonight”

Elvis Presleysadly croons in this 1960 hit, “Honey, you lied when you said you loved me / And I had no cause to doubt you / But I’d rather go on hearing your lies / Than go on living without you.”

48. The Platters, “The Great Pretender”

The Platters had a hit with “The Great Pretender,” a song about putting on a brave face while you’re nursing a broken heart. The tune is so iconic that Freddie Mercuryeven covered it.

49. Joy Division, “Love Will Tear Us Apart”

This rock classic from Joy Division describes a deteriorating relationship in heartbreaking detail: The song was inspired by frontman Ian Curtis’ failing marriage, and the track was released shortly before he took his own life. https://www.youtube.com/watch?v=zuuObGsB0No

50. Toni Braxton, “Unbreak My Heart”

Toni Braxton puts her signature alto voice to work on this ballad, letting listeners really hear the anguish in the lyrics. https://www.youtube.com/watch?v=p2Rch6WvPJE

51. Justin Timberlake, “Cry Me a River”

Justin Timberlake revealed in his book Hindsight: & All the Things I Can’t See in Front of Me, “I’ve been scorned. I’ve been pissed off. I wrote ‘Cry Me a River’ in two hours. I didn’t plan on writing it.” One thing it appears he did plan on? Casting a Britney Spears look-alike in the video.

52. Celine Dion, “It’s All Coming Back to Me Now”

For when you’re feeling nostalgic and missing an ex—but we don’t recommend calling them! https://www.youtube.com/watch?v=pDxoj-tDDIU

53. Bon Jovi, “You Give Love a Bad Name”

On top of having one of the most recognizable solos in rock, Bon Jovi’s “You Give Love a Bad Name” has an intriguing backstory—it was inspired by frontman Jon Bon Jovi’s affair with Diane Lane. https://www.youtube.com/watch?v=KrZHPOeOxQQ

54. Lady Gaga, “Million Reasons”

Lady Gaga delivers some serious agony in this song about a lover who clearly doesn’t deserve her in a relationship that clearly isn’t working—but that she’s having a hard time walking away from. Haven’t we all been there? https://www.youtube.com/watch?v=en2D_5TzXCA

55. Guns n’ Roses, “November Rain”

Axl Rose belts out one of the best songs ever about needing a break with the Guns n’ Roses classic piano-driven opus “November Rain.” https://www.youtube.com/watch?v=8SbUC-UaAxE

56. Natalie Imbruglia, “Torn”

Most people don’t realize that Natalie Imbruglia’s sole stateside hit was actually a cover—the song had been recorded twice before she made it an international smash. https://www.youtube.com/watch?v=VV1XWJN3nJo

57. The All-American Rejects, “Gives You Hell”

The All-American Rejects broke into the mainstream with the lovelorn, guitar solo-heavy “Swing Swing,” but it’s “Gives You Hell” from their third album, When the World Comes Down, that cemented their legacy in the breakup anthem hall of fame. https://www.youtube.com/watch?v=uxUATkpMQ8A

58. Alicia Keys, “Try Sleeping With a Broken Heart”

Alicia Keys promises to make it just fine without her ex, but admits she’s having a tough time doing so in this modern classic from The Element of Freedom. https://www.youtube.com/watch?v=srMBZiqNMaM

59. CeeLo Green, “F*ck You”

CeeLo Green is all of us when he spots a gold-digging ex with a new person. https://www.youtube.com/watch?v=bKxodgpyGec

60. The Cure, “Boys Don’t Cry”

The Cure had one of their biggest hits ever with this tune, which was basically an anthem for toxic masculinity before there was a term for it. https://www.youtube.com/watch?v=ZUsn4iL_l7o

61. J. Geils Band, “Love Stinks”

If you love someone who loves someone else, then yes, love stinks. https://www.youtube.com/watch?v=E0LAs7X5ybE

62. The Rolling Stones, “Angie”

You can hear the sadness in Mick Jagger’s voice when he pleads with his lover to let it all go in this Rolling Stones classic. https://www.youtube.com/watch?v=RcZn2-bGXqQ

63. Destiny’s Child, “Survivor”

Remember, if you’re considering subtweeting or slamming your ex on social media, the wise words of Destiny’s Child (specifically Kelly Rowland): “You know I’m not gon’ diss you on the Internet / Because my mama taught me better than that.” https://www.youtube.com/watch?v=Wmc8bQoL-J0

64. Rascal Flatts, “What Hurts the Most”

Rascal Flatts earned two Grammy nominations for their 2006 cover of “What Hurts the Most.” You can hear why. https://www.youtube.com/watch?v=7qH4qyi1-Ys

65. The Police, “Every Breath You Take”

The Police wrote a uniquely clever and ultra creepy song about stalking an ex—even though the lyrics aren’t at all subtle, people somehow still use this as a first dance at their weddings. https://www.youtube.com/watch?v=OMOGaugKpzs

66. The Killers, “Mr. Brightside”

The Killers combine a soaring melody with heartwrenching lyrics about being two-timed. There’s a reason this song cannot stop charting more than 15 years since its release.

67. Kanye West, “Heartless”

Before Kanye West became famous for his feud with Taylor Swift and his marriage to Kim Kardashian West, he was universally praised for 808s and Heartbreak, with “Heartless” as a standout. https://www.youtube.com/watch?v=Co0tTeuUVhU

68. U2, “With or Without You”

U2 had an instant classic with 1987’s “With or Without You,” thanks in large part to Bono’s lyrics about a toxic on-again-off-again love—all too relatable. https://www.youtube.com/watch?v=ujNeHIo7oTE

69. Kesha, “Resentment”

Kesha has a lot of sassy breakup songs (like “Thinkin’ Of You”), but her ballads really pull at the heartstrings. “The Harold Song” is a favorite among her Animals, but it’s “Resentment,” off of 2020’s High Road, that can really bring the tears: It’s a raw, stripped ode to a lover who’s gotten too comfortable from a woman who’s just about had enough—but is too depressed to take much action. https://www.youtube.com/watch?v=fJ2iBrXVkRY

70. Little Mix, “Shout Out to My Ex”

Little Mix delivered a serious breakup bop, rumored to be about Perrie Edwards’ bitter breakup from Zayn Malik. https://www.youtube.com/watch?v=bFDzhKdrN9M

71. Brandy and Monica, “The Boy Is Mine”

This 1998 smash between Brandyand Monica, two of the era’s two biggest R&B divas, was the No. 1 song for 13 weeks and the biggest-selling song of that year. Though the song itself offers little resolution for their fight over a player, the music video—starring Mekhi Phifer—is a testament to girl power.

72. Lauryn Hill, “Ex-Factor”

Anyone who’s been trapped in a toxic relationship can relate to Lauryn Hill in “Ex-Factor,” in which she essentially begs an ex to stop hurting her—even though she thinks every time will be the time he finally changes. https://www.youtube.com/watch?v=cE-bnWqLqxE

73. The Dixie Chicks, “Goodbye Earl”

The Dixie Chicks deliver an anthem of girl power about two best friends who team up to make an abusive ex “a missing person who nobody missed at all.” https://www.youtube.com/watch?v=Gw7gNf_9njs

74. Usher, “Burn”

Usher has one of the best voice of his musical generation, and this ballad—in which he’s the dumper and regrets it later—showcases it superbly. https://www.youtube.com/watch?v=t5XNWFw5HVw

75. Adele, “Someone Like You”

No one wails over lost love quite like Adele. “When I was writing it I was feeling pretty miserable and pretty lonely,” she said in an interview, “which I guess kind of contradicts ‘Rolling in the Deep.’ Whereas that was about me saying, ‘I’m going to be fine without you’, this is me on my knees really.” https://www.youtube.com/watch?v=hLQl3WQQoQ0

Blink-182 is all of us in the acoustic “What Went Wrong,” with powerful yet simple lyrics like “I hate our favorite restaurant, favorite movie, our favorite show,” and the epic refrain: “You f*cked up my life.”

77. No Doubt, “Don’t Speak”

Gwen Stefani took a cue from Fleetwood Mac: She wrote “Don’t Speak” about her own breakup from No Doubt bandmate Tony Kanal. Another good one? “Ex-Girlfriend,” also about their split. https://www.youtube.com/watch?v=TR3Vdo5etCQ

78. Jimmy Eat World, “The End Is Beautiful”

Jimmy Eat World is best known for “The Middle,” a soaring pop-punk confection about getting over a breakup or other adversity. “The End Is Beautiful,” however, is about the bittersweet ending of a relationship that wasn’t working for either party, but in which neither has animosity for the other. https://www.youtube.com/watch?v=_zA0bWbT4Dg

79. Justin Bieber, “Love Yourself”

You know what Justin Bieber really means by “love” here, and honestly, we’re here for it—and also for the quietly scathing “My mama don’t like you / And she likes everyone.” Burn! https://www.youtube.com/watch?v=oyEuk8j8imI

80. Miley Cyrus, “Wrecking Ball”

Miley Cyrushad one of her biggest hits ever with “Wrecking Ball.” The power ballad, reportedly originally written for Beyoncé, dropped as she was splitting from then-fiance Liam Hemsworth, and the all-too-literal music video has been seared in pop culture forever. https://youtu.be/My2FRPA3Gf8

81. Dashboard Confessional, “The Best Deceptions”

Chris Carrabba will forever be known for “Screaming Infidelities,” “Stolen” and “Vindicated,” but this album cut from The Places You’ve Come to Fear the Most is an earnest literal kiss-off to a cheating lover: “So kiss me hard / Because this will be the last time that I let you.” https://www.youtube.com/watch?v=0joOZ_XsPFI

82. Savage Garden, “The Lover After Me”

In this album cut from Affirmation, Darren Hayes paints a vivid picture of life after a breakup when your ex has moved on, but you can’t manage to do the same. https://www.youtube.com/watch?v=ft6k6Gk7t9Y

83. Smokey Robinson and The Miracles, “Tracks of My Tears”

Smokey Robinson and The Miracles changed the ending of “The Tracks of My Tears” at the last minute to end with the iconic chorus instead of the “I Need You” refrain. https://www.youtube.com/watch?v=rNS6D4hSQdA

84. John Mayer, “Dreaming With a Broken Heart”

Mayer delivers a hauntingly beautiful song about heartbreak with his trademark imagery: “Do I have to fall asleep with roses in my hands?” https://www.youtube.com/watch?v=syO6Oi7-4TM

85. Amy Winehouse, “Back to Black”

Considered one of the late chanteuse’s greatest songs, as well as one of her biggest stateside hits, “Back to Black” is Winehouse at her best: Heartbroken, jazz-inflected and with a touch of gallows humor.

86. Ariana Grande, “Thank U Next”

After a series of high-profile relationships, Ariana Grandename-checked almost all of them in “Thank U Next,” released just after her split from Pete Davidson. It’s not just a breakup song about her exes, however—it’s also a love song to herself.

87. Tegan and Sara, “Wake Up Exhausted”

Tegan and Sara nail how, well, exhausting it is to be in a relationship that’s on the rocks and on the verge of ending. https://www.youtube.com/watch?v=ZtpaFbspMvc

88. St. Vincent, “New York”

St. Vincent gets reflective about a relationship’s end in “New York,” singing, “I have lost a hero / I have lost a friend / But for you, darling / I’d do it all again.” https://www.youtube.com/watch?v=4TPqUvy1vYU

89. Harry Nilsson, “You’re Breaking My Heart”

Harry Nilsson keeps it quite simple in this classic: “You’re breaking my heart / You’re tearing it apart / So f*ck you.” We couldn’t have said it better ourselves. https://www.youtube.com/watch?v=MiLKTKd5pgs

90. Hall & Oates, “She’s Gone”

In what may be a prequel to “Maneater,” Hall & Oates lament a lover who left them in the dust in this sad tune. https://www.youtube.com/watch?v=bnVXIUyshng

91. Bon Iver, “Skinny Love”

Justin Vernonsays that “Skinny Love,” the debut single from Bon Iver, is “about that time in a relationship that I was going through; you’re in a relationship because you need help, but that’s not necessarily why you should be in a relationship. And that’s skinny.” https://www.youtube.com/watch?v=95FyXUHv8hk

92. Erykah Badu, “Tyrone”

Erykah Badu revealed that “Tyrone” came about after improvising onstage with her band and background singers, and that the live version was released to radio the very next day. She later said of the song’s legacy, “It’s like an ex-boyfriend who won’t stop following me. And it’s a blessing at the same time because it’s an anthem.” https://www.youtube.com/watch?v=Jh-Swub_2UM

93. Oasis, “Don’t Look Back in Anger”

“Don’t Look Back in Anger” was the first Oasis single to feature lead vocals from Noel Gallagher and not brother Liam. Noel admitted of the tune, “I remember writing it in Paris on a rainy night. We had just played a strip club: our set finished, the strippers came on. We were nothing, an insignificant little band. And I remember going back to my hotel room and writing it, and thinking, ‘That’ll be pretty good when we record it.’ If I’d have known that night what I know now about people playing it at f*cking funerals and weddings, I’d never have finished the song. Too much pressure.” https://www.youtube.com/watch?v=cmpRLQZkTb8

94. Taylor Swift, “We Are Never Ever Getting Back Together”

Swift cemented her status as breakup song queen with “We Are Never Ever Getting Back Together,” the lead single from Red. The song was her first No. 1 single and became one of the bestselling singles worldwide with global sales of $7 million. Swift said the song’s inspiration was from a pal of an ex who stopped in the studio when she was recording Red with producers Max Martin and Johan Shellback. “He starts talking about how he’s heard we were getting back together and that was not the case,” Swift told ABC News. “When he leaves, Max and Johan are like, ‘So what’s the story behind that?’ And so I start telling them the story of break up, get back together, break up, get back together—just, ugh, the worst.” She continued, “Max says, ‘This is what we’re writing. We’re writing this song,’ and I picked up the guitar and just started singing, ‘We are never…’ It just happened so fast. It was so much fun.”

95. Avril Lavigne, “My Happy Ending”

Avril Lavignesaw her biggest breakthrough successes with songs that reeked of juvenile rebellion, like “Complicated” (about essentially not wanting to date a poser) and “Sk8r Boi.” “My Happy Ending,” from her sophomore effort Under My Skin, retains some of Lavigne’s youthful naivete, but sees it—and her heart—shattered by a grownup love gone wrong.

96. Squeeze, “Black Coffee In Bed”

Squeezewrote one of the catchiest songs ever about what lovers leave behind in “Black Coffee in Bed.”

97. Jewel, “You Were Meant for Me”

Jewelshows and doesn’t tell with her songwriting in “You Were Meant for Me,” and her lyrics are so vivid in their descriptions of her breakfast that you can see exactly what she’s going through: The banality of a broken heart.

98. Miranda Lambert, “Mama’s Broken Heart”

Co-written by Kacey Musgraves, “Mama’s Broken Heart” depicts a bombshell breakup in darkly hilarious terms: “I wish I could be just a little less dramatic / Like a Kennedy when Camelot went down in flames / Leave it to me to be holdin’ the matches / When the fire trucks show up and there’s nobody else to blame.”

99. Gotye feat. Kimbra, “Somebody That I Used to Know”

Gotye is every ex-boyfriend who just wanted to stay friends after breaking up, even though you just wanted to be left alone. We are all Kimbra here. https://www.youtube.com/watch?v=8UVNT4wvIGY

100. Rihanna, “Breakin’ Dishes”

For when a cheating man has you angry enough to really get heated, literally: “I’m killing time, you know bleaching your clothes / I’m roasting marshmallows on the fire / And what I’m burning is your attire.” https://www.youtube.com/watch?v=9SYUveBAfCU Need some girl power to cheer yourself up? Listen to these great feminist anthems!

100 Best Breakup Songs of All Time - 53