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The Best '90s Breakup Songs

Updated February 24, 2020 985 votes 75 voters 3.3k views30 items

List RulesVote up the breakup songs that are better than a full pint of Ben & Jerry's.

It's hard to get over an ex, but the best '90s breakup songs can get you through like few other eras of music. What better place could there be to look for angry breakup songs than the age of grunge? Who better to reinvent yourself (or wallow) with than '90s it-girls like Britney Spears? 

Whether you favor R&B, alternative rock, or country, this list of good '90s breakup songs has something to help heal your ailing heart. 

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  • 1

    Don't Speak

    No Doubt
    41
    11

    AlbumsTragic Kingdom

    ComposerGwen Stefani, No Doubt, Eric Stefani

    ProducerMatthew Wilder

    Length (seconds)4:23

  • 2

    You Oughta Know

    Alanis Morissette
    32
    6
  • 3

    Nothing Compares 2 U

    Sinead O'Connor
    40
    16
  • 4

    AlbumsPieces of You

    ComposerJewel

    Length (seconds)5:40

  • 5

    A Long December

    Counting Crows
    25
    8

    AlbumsRecovering the Satellites

    ComposerAdam Duritz, David Bryson

    Length (seconds)4:57

  • 6

    Torn

    Natalie Imbruglia
    27
    11
  • 7

    End of the Road

    Boyz II Men
    30
    15

    AlbumsCooleyhighharmony, Plztinum Collection

    ComposerBabyface, L.A. Reid, Daryl Simmons

    ProducerL.A. Reid, Daryl Simmons, Babyface

    Length (seconds)5:47

  • 8

    Stay (I Missed You)

    Lisa Loeb, Nine Stories
    30
    16

    AlbumsTails

    ComposerLisa Loeb

    ProducerJuan Patiño

    Length (seconds)2:58

  • 9
    30
    19

    AlbumsThe Sign

    ComposerDiane Warren, Albert Hammond

    ProducerPer Adebratt, Tommy Ekman

    Length (seconds)3:48

  • 10

    Cryin'

    Aerosmith
    25
    16

    AlbumsGet a Grip

    ComposerSteven Tyler, Joe Perry, Taylor Rhodes

    ProducerBruce Fairbairn

    Length (seconds)5:9

  • 11

    Always

    Bon Jovi
    19
    11
  • 12

    Un-Break My Heart

    Toni Braxton
    20
    14

    AlbumsSecrets

    ComposerDiane Warren

    Length (seconds)4:5

  • 13

    Wicked Game

    Chris Isaak
    22
    16

    AlbumsHeart Shaped World

    ComposerChris Isaak

    ProducerErik Jacobsen

    Length (seconds)4:47

  • 14

    Ex-Factor

    Lauryn Hill
    12
    7

    AlbumsThe Miseducation of Lauryn Hill

    ComposerLauryn Hill

    ProducerLauryn Hill

    Length (seconds)5:27

  • 15

    Albums...Baby One More Time

    ComposerEric Foster White

    ProducerEric Foster White

    Length (seconds)4:34

  • 16

    You Oughta Know

    FORK
    13
    10

    AlbumsCover to Cover, Helsinki

    ComposerAlanis Morissette, Glen Ballard

    Length (seconds)4:9

  • 17

    Nobody Knows

    The Tony Rich Project
    11
    9
  • 18

    Without You

    Mariah Carey
    20
    23

    AlbumsMusic Box

    ComposerPeter Ham, Tom Evans

    ProducerWalter Afanasieff, Mariah Carey

    Length (seconds)3:31

  • 19

    Damn, I Wish I Was Your Lover

    Sophie B. Hawkins
    13
    13
  • 20

    Sleep to Dream

    Fiona Apple
    12
    13

    AlbumsTidal

    ComposerFiona Apple

    Length (seconds)4:8

  • 21

    Never Ever

    All Saints
    15
    17
  • 22

    Special

    Garbage
    8
    9

    AlbumsVersion 2.0

    ComposerGarbage

    ProducerGarbage

    Length (seconds)3:40

  • 23

    Miss World

    Hole
    11
    13
  • 24

    Try

    Macy Gray
    16
    21
  • 25

    Insensitive

    Jann Arden
    10
    12

    AlbumsLiving Under June

    ComposerAnne Loree

    Length (seconds)4:14

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List Rules: Vote up the breakup songs that are better than a full pint of Ben & Jerry's.