The 100 Best Breakup Songs of All Time

Let’s face it: Breakups are the worst. Whether you’re on the receiving end of a split or the one doing the splitting, you’re bound to experience intense feelings of sadness in the days following a separation. But there are a few time-tested ways to ease the pain that comes with a breakup. One of the greatest? Compiling a feel-good playlist of the best breakup songs.

While sobbing along to gut-wrenching breakup songs may seem counterproductive, research has shown that doing so actually helps boost our moods. In fact, in one 2014 study published in PLOS ONE, participants expressed feelings of relief after going on a sad-song bender, noting that the tunes made for a great emotional outlet. So whether you need some feel-good motivation to get back in the saddle, or just a good ol’ ugly cry, we have you covered. These are the 100 best breakup songs of all time.

1 | "Respect" by Aretha Franklin (1967)

Atlantic

The legendary Aretha Franklin set the standard for what it means to be valued in a relationship with this 1967 hit. (R-E-S-P-E-C-T!)

2 | "We Are Never Ever Getting Back Together" by Taylor Swift (2012)

Big Machine

What’s a breakup song playlist without Taylor Swift? The Queen of Heartbreak blessed us with this breakup bop in 2012, showing us how to say "see ya" to the exes who want us back after treating us poorly.

3 | "Dancing Queen" by ABBA (1976)

Atlantic

This classic hit by the Swedish group ABBA is guaranteed to lift your spirits. And now that you're single, it's about to be your jam while you get ready for all those girls nights you better be planning.

4 | "Tears Dry on Their Own" by Amy Winehouse (2006)

Island

British jazz songstress Amy Winehouse knew a thing or two about heartbreak. The artist had a number of tumultuous relationships throughout her short life, but rather than let her pain be for naught, she channeled it into a series of smash hits over the course of her career, including this 2006 track from her album Back to Black.

5 | "It Ain’t Me" by Kygo and Selena Gomez (2017)

Interscope

Selena Gomez dropped this overnight dance club hit after her very public second split from boyfriend Justin Bieber. With lyrics like, “I’ll take with me the Polaroids and the memories, but you know I’m gonna leave behind the worst of us,” Gomez reminds listeners of the importance of walking away from a relationship the moment it turns sour.

6 | "No Scrubs" by TLC (1999)

Arista

One of the noteworthy '90s groups, TLC dropped this hit in 1999 as a rallying cry for women everywhere, with an underlying message that tells you it's absolutely fine (and seriously empowering) to say "no, thanks" to anyone who’s not worth your time.

7 | "Screaming Infidelities" by Dashboard Confessional (2000)

Animal Manufacturing Co.

Who could forget the iconic scene from Laguna Beach where Laguna bad boy Jason Wahler leaves his longtime girlfriend high and dry to secretly play poker with Alex Murrel? This 2000 hit from Dashboard Confessional provided an emotional backdrop to the scene, making it a historic moment for dramatic early aughts teen television.

8 | "Let It Go" by James Bay (2015)

Republic

James Bay’s first hit was a heartbreaking ballad about knowing when to call it quits. The song, which dropped in 2015, gave us all the feels, as the artist notes how difficult it can be to walk away from a relationship that is no longer working, even when you know it’s time to let go: “Now we're slipping near the edge, holding something we don't need. Oh, this delusion in our heads is gonna bring us to our knees.”

9 | "Bleeding Love" by Leona Lewis (2007)

Syco

This 2007 smash from Leona Lewis about going back to someone toxic is relatable on so many levels. But aside from feeling seen by the singer’s lyrics, belting the chorus at the top of your lungs is also surprisingly therapeutic.

10 | "Girl" by Maren Morris (2019)

Columbia Nashville

In her 2019 track, Maren Morris delivers the anthem we never knew we needed. In it, the artist begs women to see how special they are, letting them know they’ll make it to the end of the tunnel, even though it may not feel that way.

11 | "It’s Not Right but It’s Okay" by Whitney Houston (1998)

Arista

Whitney Houston released the ultimate girl power hit in 1998 with “It’s Not Right but It’s Okay.” The lyrics follow a woman who catches her man cheating, and subsequently kicks him out: “It's not right, but it's okay, I'm gonna make it anyway. Close the door behind you, leave your key, I'd rather be alone than unhappy.” Between that and Houston’s powerhouse vocals, you’re bound to walk away feeling empowered.

12 | "One Last Song" by Sam Smith (2017)

Capitol

Sam Smith knows how to sing a love song, and while some of their tunes will break your heart, this upbeat bop provides listeners the chance to give one final goodbye to ghosts of relationships past.

13 | "Thinking of You" by Kesha (2012)

Kemosabe

In this empowering tongue-in-cheek tune from Kesha, the singer says she’ll be thinking of her ex when her song gets played on the radio. “You had your chance,” she tells him.

14 | "Are You Happy Now?" by Michelle Branch (2003)

Maverick Records

Honestly, what’s not to love about a Michelle Branch hit, and this one is definitely a standout. Just try to not sing along to the chorus. We dare you.

15 | "The Greatest" by Sia (2016)

RCA

This musical tour-de-force from Sia is both fun and empowering. “Don’t give up,” she says to her listeners, no matter what the obstacle.

16 | "Survivor" by Destiny’s Child (2001)

Columbia

In this early aughts hit, ultimate girl group Destiny’s Child tell their female listeners to kick their significant others to the curb if they’re not feeling appreciated. “Now that you’re out of my life, I’m so much better.” Preach, ladies.

17 | "Be Careful" by Cardi B (2018)

Atlantic Records

Cardi B takes no prisoners, especially in this song. Put to a seriously snappy beat, the singer tells her boyfriend to “be careful” and not misstep again, or else risk losing her.

18 | "Un-Break My Heart" by Toni Braxton (1996)

LaFace

Toni Braxton knows how to lay down a hit, and this song is no exception. This is arguably the most iconic breakup song of all time. If you need a good cry, this is your jam.

19 | "Dog Days Are Over" by Florence + the Machine (2009)

Island

Lead singer Florence Welch delivers verse after verse of raw vocals and feel-good lyrics on this upbeat track, making this the perfect mood-changer when you’re having a down day post-breakup. Or, well, ever.

20 | "Dancing on My Own" by Robyn (2010)

Konichiwa

There’s a reason Swedish pop singer Robyn has been in the game for so long: She’s a songwriting genius. And the 2010 hit “Dancing On My Own” is no exception. You may remember it from Season 1 of Girls, or any dance club you visited in the last 10 years. It’s a sad song set to a catchy beat. In other words: perfection.

21 | "Don’t Speak" by No Doubt (1995)

Interscope

There’s no better way to combat post-breakup blues than with a Gwen Stefani singalong—and this is the perfect jam for it.

22 | "Without Me" by Halsey (2018)

Capitol

In this 2018 chart-topper, Halsey sings of a difficult breakup (with G-Eazy, perhaps?). The song is about building someone else up in a relationship, only to have them break your heart in the end. In short, it’s a breakup must-listen.

23 | "Since U Been Gone" by Kelly Clarkson (2004)

RCA

Nobody does breakup lyrics like Kelly Clarkson, and “Since U Been Gone” is proof. (Plus, who can forget the song’s epic music video?) If belting this tune at the top of your lungs doesn’t put a smile on your face, we don’t know what will.

24 | "Wrecking Ball" by Miley Cyrus (2013)

RCA

If 2013 gave us anything, it was the music video for “Wrecking Ball,” where a naked Miley Cyrus sang her heart out while swinging from a giant, well, wrecking ball. And while the music video raised some eyebrows, the lyrics share so much raw emotion that you’d be remiss if you let a breakup go by without jamming to this song at least once. (Wrecking balls sold separately.)

25 | "Somebody That I Used to Know" by Gotye feat. Kimbra (2011)

Eleven

The rhythm! The harmony! The emotion! This instant hit from Gotye is as fun to dance along to as it is to sing, making it the perfect prescription for post-breakup heartache.

26 | "Take a Bow" by Rihanna (2007)

Def Jam

It’s hard to pick only one Rihanna song for a breakup list. (Don’t worry: We didn’t!) But this '07 hit from the pop star’s third studio album is a true standout, giving listeners epic post-breakup revenge lyrics: “Don’t tell me you’re sorry ‘cause you’re not, baby when I know you’re only sorry you got caught.” You tell ‘em, RiRi!

27 | "Love Myself" by Hailee Steinfeld (2015)

Universal

This song needs no introduction. The brainchild of Hailee Steinfeld, this is a feel-good bop that will have you forgetting you ever had a breakup in the first place. Ex-boyfriend who?

28 | "Back to Black" by Amy Winehouse (2006)

Island

Remember how we said Amy Winehouse knew how to write a breakup song? Well, here’s further proof. In this 2006 hit, the singer-songwriter mulls over the idea of going back to her ex, even though she knows he’s bad for her health. (Been there, Amy.) The beat is iconic, as is the artist.

29 | "You Oughta Know" by Alanis Morissette (1995)

Maverick

No breakup playlist is complete without Alanis Morissette, and “You Oughta Know” should be at the top of your list. It’s an empowering ballad from one of the strongest women out there. What’s not to love?

30 | "I Can’t Make You Love Me" by Bonnie Raitt (1991)

Capitol

If you need to just curl up in a ball on the couch with a bottle of Merlot and cry your eyes out, Bonnie Raitt is here for you. This song has been covered dozens of times (by everyone from Bon Iver to George Michael), but Bonnie did it first, and arguably does it best. So go ahead—throw on sweats, grab some Kleenex, and give yourself a good cry. We won’t judge.

31 | "Cry Me a River" by Justin Timberlake (2002)

Jive

Take a walk down memory lane by recalling the iconic relationship between pop darlings Justin Timberlake and Britney Spears. While their love story didn’t last long, this breakup song sure did. (And their dramatic breakup made for an even more dramatic music video.)

32 | "Never Again" by Kelly Clarkson (2007)

RCA

What, did you think we’d only give Kelly Clarkson one spot on this list? In “Never Again,” she blesses listeners with a powerful dose of “you’re going to regret cheating on me” medicine, and we’re here for it.

33 | "Ugly Heart" by G.R.L. (2014)

RCA

Looks aren’t everything, G.R.L. reminds us in this hit from 2014. With lyrics like, “It’s such a pity a boy so pretty could have an ugly heart,” it’s hard not to bop along to this track. And if you leave a note on your ex’s car with these lyrics on it, we won’t tell.

34 | "Irreplaceable" by Beyoncé (2006)

Columbia

If you need to be reminded of how special you are, look no further than this '06 bop from Beyoncé. Well, maybe look to the left, to the left. (See what we did there?)

35 | "Call Out My Name" by The Weeknd (2018)

Republic

Canadian singer-songwriter Abel Tesfaye, more commonly known as The Weeknd, is rumored to have penned this song after his breakup with Selena Gomez, and the lyrics don’t hint otherwise: “Guess I was just another pit stop 'til you made up your mind.” Ouch. Been there, Abel!

36 | "Summertime Sadness" by Lana Del Rey (2012)

Interscope

While this overnight hit from Lana Del Rey may not be the literal definition of a breakup song, the tune’s title and melancholy melody point to something deeper, particularly through the lyrics that kick off the chorus: “Kiss me hard before you go, summertime sadness.”

37 | "Happier" by Marshmello feat. Bastille (2018)

Astralwerks

Oftentimes, breakup songs put listeners in the seat of the person getting his or her heart broken, but in this 2018 hit from music producer and DJ Christopher Comstock (known professionally as Marshmello) and Bastille frontman Dan Smith, we hear from the other side of the aisle. The lyrics tell the story of a relationship that’s come to an end, and remind us that sometimes, leaving is the best thing you can do for someone.

38 | "It’s Too Late" by Carole King (1971)

Sony Music Entertainment

Name any top-40 hit from the '60s or '70s, and there’s a very good chance Carole King wrote it. But this song, which the artist conceived and sang herself, is arguably one of her most famous—and heartbreaking.

39 | "Skinny Love" by Bon Iver (2007)

4AD

If singer-songwriter Justin Vernon knows anything, it’s how to tug at a person’s heartstrings. This song from the artist’s debut album, For Emma, Forever Ago, made its way up the charts quickly thanks to its moving lyrics and Vernon’s unique sound. Listen to it if you need a good cry.

40 | "Someone Like You" by Adele (2011)

XL

From Adele’s second studio album comes “Someone Like You,” a powerful chart-topper that tells the story of moving on after a now-defunct relationship. Adele makes it look so easy!

41 | "It Ain’t Me Babe" by Bob Dylan (1964)

Columbia

While “It Ain’t Me Babe” has been covered by music legends like Johnny Cash and June Carter, the original was recorded by Bob Dylan. Keeping true to Dylan’s signature part-folk, part-bluegrass style, the song is a pared-down ballad that sounds like it belongs at the beginning of an indie movie about moving on. And move on you should!

42 | "I’m Gonna Find Another You" by John Mayer (2006)

Columbia

If you were to google “love song,” a photo of John Mayer would likely appear alongside it. Well, maybe not really, but it should: The artist has churned out hit after heartbreaking hit over the course of his decades-long career, many of which spin tales of failed relationships. This may be one of our favorites, though, thanks to its promise of love after heartbreak.

43 | "Stay" by Rihanna feat. Mikky Ekko (2012)

Def Jam

This song will make your heart hurt, but in the best way possible. The duet from Rihanna and Mikky Ekko is equal parts painful and beautiful, and the perfect song to pop on your Spotify playlist if you need to let out a few tears. Or more than a few.

44 | "Don’t Think Twice, It’s All Right" by Bob Dylan (1963)

Columbia

Given that Bob Dylan is arguably one of the most iconic artists of all time, it’s only right his name appears on this list twice. While Dylan’s not known as being a writer of love songs per se, many interpret this tune to be about a splintered relationship.

45 | "Try" by Pink (2012)

RCA

“Funny how the heart can be deceiving,” Pink sings in this 2012 smash, hitting the nail on the head for just how easy it can be to get hurt when you open up to someone. Lucky for us, belting this song out at the top of your lungs can mend a broken heart. (Well, mostly.)

46 | "Leave (Get Out)" by JoJo (2004)

Blackground

Early aughts singer-songwriter JoJo is to love songs what peanut butter is to jelly. The artist churned out a number of breakup hits in the early '00s, beginning with the catchy showstopper “Leave (Get Out).”

47 | "Shout Out to My Ex" by Little Mix (2017)

Syco

Nothing puts pep back in your step like a solid girl power anthem from British girl group Little Mix, and this song takes the cake for revenge bops.

48 | "(I Know) I’m Losing You" by The Temptations (1966)

Motown Records

This 1966 hit from Motown all-stars The Temptations may just be one of the best songs to sing (or cry) along to, but thanks to its catchy beat, it’s also an excellent song to get you on your feet. Do with it what you will!

49 | "Love Yourself" by Justin Bieber (2015)

Def Jam

Arguably one of the biggest hits from pop singer Justin Bieber, first appearing on his Purpose album, "Love Yourself" offers a subtle yet obvious message: If I’m not giving you what you want, then leave. It’s an undeniably catchy tune with an even more hypnotic music video. This one’s a must-listen!

50 | "Use Somebody" by Kings of Leon (2008)

RCA

Nashville-bred rock band Kings of Leon have perfected the art of writing a love song, and “Use Somebody” is a quintessential example. The track subtly recounts the days after a breakup: “Off in the night, while you live it up, I'm off to sleep,” and leaves you reeling from its haunting sound.

51 | "Always Be My Baby" by Mariah Carey (1995)

Columbia

Mariah Carey taught the world what love was with her 1995 album Daydream. This track is a particular standout, and—when performed with passion at karaoke—it might just cure you of your heartbreak entirely.

52 | "Stitches" by Shawn Mendes (2015)

Island

Some artists write love songs, and some artists write love songs. Shawn Mendes falls in the second category, coming onto the pop scene in 2015 with this heartbreaker of a hit. The song’s lyrics are beyond relatable, and a surefire way to get you over your recent breakup. (For today, at least.)

53 | "Dreaming With a Broken Heart" by John Mayer (2006)

Aware Records

As the name suggests, John Mayer’s “Dreaming With a Broken Heart” may just... break your heart. The song recalls the raw emotion that enshrouds a person in the days following a breakup, and in true Mayer fashion, the lyrics paint a poetic picture: “Do I have to fall asleep with roses in my hand?” Swoon.

54 | "Alive" by Kehlani (2015)

TSNMI

If you need a melodic pick-me-up after a breakup, look no further than Kehlani’s “Alive.” While the tune itself is laid-back, the lyrics call to mind energy and strength, with lines like “We were in so deep, we could barely tread, but now I found a way to heal myself instead,” and, “I deserve a love that is gonna last, but until then I will just raise this glass.”

55 | "No Tears Left to Cry" by Ariana Grande (2018)

Republic

Ariana Grande has no shortage of hits about relationship mishaps, but unlike some of her other breakup songs, “No Tears Left to Cry” is more of a call to action than anything else, encouraging listeners to get up and get out after a breakup. Play this tune on the way to meet your friends for drinks!

56 | "Forget You" by Cee Lo Green (2010)

Elektra

Cee Lo Green does breakup songs best. Rather than shed tears over a failed relationship, the artist wants you to say “forget you,” and move on. Hey, if he can do it, so can you.

57 | "The Scientist" by Coldplay (2002)

Capitol

There’s no song you can count on for a good cry like Coldplay’s “The Scientist.” Chris Martin’s haunting vocals alone will bring you to tears, and the tune’s beautiful lyrics only add fuel to the fire. You may end up sobbing by the end of the song's instrumental interlude, but trust us, you’ll feel better once you do.

58 | "This Love" by Maroon 5 (2002)

Interscope

Before Adam Levine was touring solo, he was writing songs about Jane, starting with this hit from his debut album. There’s nothing better than early aughts Maroon 5 and their signature sound. Consider it over-the-counter breakup medicine.

59 | "Hit ‘Em Up Style (Oops!)" by Blu Cantrell (2001)

Arista

If you can’t beat ‘em, spend their money! Or at least that’s what artist Blu Cantrell insinuates in her relentlessly catchy 2001 hit “Hit ‘Em Up Style.” We can’t say we blame her!

60 | "Breakeven" by The Script (2008)

Sony Music

The Script’s 2008 hit “Breakeven” is a breakup song at its best, and quite possibly describes everything you’re feeling post-split. This record pairs best with your favorite takeout and a glass of Pinot.

61 | "Thank U, Next" by Ariana Grande (2019)

Republic

Ariana Grande delivered the breakup song to end all breakup songs with one of 2019's biggest hits, instructing us all to Marie Kondo our relationships by thanking them for their service, and then letting them go.

62 | "Before He Cheats" by Carrie Underwood (2005)

Arista

Don’t mess with Carrie Underwood, especially if you feel any sort of attachment to your car. That’s the message behind “Before He Cheats,” and if you’re reeling after a bad breakup, this is the song for you. (Just don’t do anything Carrie wouldn’t do.)

63 | "Go Your Own Way" by Fleetwood Mac (1977)

Warner Bros.

No band does heartache or heartbreak like Fleetwood Mac, and “Go Your Own Way” is solid proof. The song tackles unrequited love in a way only Fleetwood Mac can, and makes you feel inexplicably seen.

64 | "Gives You Hell" by The All-American Rejects (2008)

Interscope

Ah, revenge pop. The All-American Rejects may not have done it first, but they certainly did it best with “Gives You Hell.” Play this one on full blast (preferably while driving past your ex’s house).

65 | "Who Knew" by Pink (2006)

LaFace

Pink’s ability to pen songs about heartbreak is uncanny, and in “Who Knew,” the artist takes this talent to the next level.

66 | "Out Of the Woods" by Taylor Swift (2014)

Big Machine

Rumored to have been written about her breakup with former One Direction member Harry Styles, Taylor Swift’s 2014 song “Out Of the Woods” is an homage to relationships that are seemingly doomed from the start.

67 | "Nothing Breaks Like a Heart" by Mark Ronson feat. Miley Cyrus (2018)

RCA

The 2018 hit from superduo Mark Ronson and Miley Cyrus calls to mind a new-age Janis Joplin, and with its equal parts sad and catchy tune, the track is sure to make it to the top of your breakup songs playlist.

68 | "Love Is a Battlefield" by Pat Benatar (1983)

Chrysalis

Pat Benatar speaks the truth with this 1983 hit, detailing how heartbreaking love can be, but assuring listeners that everyone’s in it together: “Heartache to heartache, we stand.” Amen, sister.

69 | "I Used To Love Him" by Lauryn Hill feat. Mary J. Blige (1998)

Ruffhouse

This '98 hit pairs Lauryn Hill’s soulful voice with lyrics that will lift you off the ground. With words like, “Sacrificed too much and waited in vain, gave up my power, ceased being queen,” Lauryn Hill and Mary J. Blige give you all the makings of an uplifting girl-power anthem, one that reminds you that you’re better off alone as a queen than unhappy in a relationship.

70 | "Palace" by Sam Smith (2017)

Capitol

A standout from Smith’s sophomore album, “Palace” may sound like just another sad love song, but listen closely and you’ll realize Smith says that despite heartbreak, “Real love is never a waste of time.”

71 | "Total Eclipse of the Heart" by Bonnie Tyler (1983)

Columbia

Oh, Bonnie Tyler: What did we do to deserve you? Nothing, but we appreciate this 1980s knockout hit anyway. Put this song on full blast in your car and drive around the block. Trust us, you won’t regret it.

72 | "So Gone" by Monica (2003)

RCA

Monica does heartbreak right in this 2003 R&B track. This song is part tragic, part empowering, but all worth the post-breakup download.

73 | "I’m Coming Out" by Diana Ross (1980)

Motown Records

Thank you, Diana Ross, for this essential anthem. Need a night out with your girlfriends to forget your bad breakup? Get ready to this song, and you’re guaranteed to have the best night ever.

74 | "So Yesterday" by Hilary Duff (2003)

Buena Vista

Who can forget this iconic bop from early aughts darling Hilary Duff? If you need both a Disney Channel throwback and a song about moving on after a breakup, this song is for you.

75 | "You Were Meant For Me" by Jewel (1995)

Atlantic

If Jewel had a LinkedIn profile, her skills would be: singing, playing the guitar, and writing songs that make you want to cry. This track is the emotional outlet you’ve been looking for, so whether you want to sing along at the top of your lungs or profess your love to a plate of chocolate chip cookies, this song is here for you.

76 | "You Should Be Here" by Kehlani (2015)

TSNMI

Kehlani’s voice shines in this 2015 track, which is an emotional rollercoaster of a song if there ever was one. You’ll laugh, you’ll cry, you’ll cry some more—but overall, you’ll be glad you added this one to your playlist.

77 | "Big Girls Cry" by Sia (2014)

RCA

Nothing is more affecting than Sia’s voice, particularly in this 2014 song, where she talks not of love and loss, but of the absence of love altogether. Confused? Give this track a listen and you’ll see what we mean.

78 | "You Give Love a Bad Name" by Bon Jovi (1986)

Mercury

We all know someone who gives love a bad name, but that person is notJon Bon Jovi. (In fact, he’s been married to his spouse for over 30 years!) Give this song a listen if you need to sing at the top of your lungs. Or play an epic air guitar.

79 | "I Could Use a Love Song" by Maren Morris (2016)

Columbia Nashville

A less-than-traditional breakup song, this track by country crooner Maren Morris talks about needing to rediscover what love is, an emotion we’ve all felt at one point or another. This tune’s catchy, so don’t play it unless you want it stuck in your head for three days. (Not a bad problem to have, in our opinion!)

80 | "All I Could Do Was Cry" by Etta James (1963)

Universal Music Group

Sometimes, you just need a good cry after a breakup. Etta James knows a little something about that, and on this track, she acknowledges the need to let it all out when you feel like you can’t go on.

81 | "Too Good at Goodbyes" by Sam Smith (2017)

Capitol

Sam Smith is arguably the most vulnerable they've ever been on this 2017 track. In it, the artist admits to having the tendency to walk away from relationships prematurely out of fear of getting hurt. We’ve all been there, Sam.

82 | "Happy Face" by Destiny’s Child (2001)

Columbia

If you need an instant mood boost, “Happy Face” has you covered. An upbeat tune from Destiny’s Child’s award-winning 2001 album Survivor, the song encourages listeners to choose happiness, despite what the world may throw at you. Sometimes we just need a gentle reminder of what’s important, am I right?

83 | "Slow Dancing in a Burning Room" by John Mayer (2006)

Columbia

Arguably one of the most heartbreaking songs on the artist’s 2006 album, Continuum, this song by Mayer offers a metaphorical warning against “slow dancing in a burning room,” or trying to make a relationship work, despite the fact that it isn’t.

84 | "Empty Space" by James Arthur (2018)

Columbia

If breakup songs had a poster child, it would be James Arthur. The pop artist’s smoky sound alone is enough to move you, but listen to the lyrics if you need to wallow for a few minutes. (We won’t tell!)

85 | "I Knew You Were Trouble" by Taylor Swift (2012)

Big Machine

No breakup playlist is complete without “I Knew You Were Trouble.” If you’re angry, hurt, sad, or even happy about your split, throw this song on at full volume for a feel-good jam session.

86 | "Miss You All the Time" by O.A.R. (2019)

Black Rock

As the song’s title may suggest, O.A.R.’s 2019 tune is bound to make you feel things. But don’t worry, the track is equal parts upbeat and emotional, so you can sneak in a quick cry between verses.

87 | "These Boots Are Made For Walkin’" by Nancy Sinatra (1966)

Reprise

Frank Sinatra’s daughter Nancy Sinatra dropped this catchy hit in 1966, and with lyrics like, “You keep playing where you shouldn't be playing, and you keep thinking that you'll never get burnt,” singing this anthem is undeniably the best medicine for your single girl’s night out comeback tour.

88 | "Advice" by Kehlani (2016)

Atlantic

“It’s time to take my own advice,” Kehlani croons on this charming 2016 track. The song’s rhythmic verses reveal the artist choosing to look inward for satisfaction, rather than find it in someone else. Now that’s some advice we can get behind.

89 | "Stronger (What Doesn't Kill You)" by Kelly Clarkson (2011)

RCA

It may appear as though Kelly Clarkson is monopolizing this list, but that’s only because the artist has the formula for breakup songs dialed-in. (Well, that and her killer voice.) “Stronger (What Doesn't Kill You)” may be the most iconic of all of Clarkson’s hits, a song that is sure to put the pep back in anyone’s step after a failed relationship.

90 | "I Hope You Find It" by Miley Cyrus (2010)

Hollywood

“Am I supposed to hang around and wait forever?” Cyrus asks in this 2010 track from the Nicholas Sparks romance The Last Song.

91 | "Two Nights" by Lykke Li feat. Aminé (2018)

RCA

The unlikely duo that is Swedish singer-songwriter Lykke Li and rapper Aminé dropped this chef’s kiss of a song in 2018. Capitalizing on Lykke Li’s unique and haunting sound, the song details a relationship that is now broken, with the singer at one point lamenting, “Somebody else, I know you’re out there with someone else. All by myself, why can’t you need me and nothin’ else?”

92 | "With or Without You" by U2 (1987)

Island

U2 knows how to write love songs, and breakup songs, and everything in between. (And we’d definitely categorize this one as an “in between.”) You know the phrase “can’t live with ‘em, can’t live without ‘em”? This song is essentially that, put to a highly catchy tune.

93 | "Stronger" by Britney Spears (2000)

Jive

No playlist is complete without at least one bop from pop princess Britney Spears, and in this case, that bop is “Stronger.” This song is the ultimate in post-breakup pick-me-ups, and the fastest way to feeling better after a split. Britney cures all!

94 | "Ex’s & Oh’s" by Elle King (2014)

RCA

Elle King’s 2014 hit “Ex’s & Oh’s” is the song you play when you want to feel equal parts sexy and powerful—and who doesn’t want that?

95 | "End Of The Road" by Boyz II Men (1992)

LaFace

Boyz II Men are experts in the art of crooning, and in their 1992 smash hit “End Of The Road,” the band tackles breaking up as only Boyz II Men can: with a whole lot of sexy harmony.

96 | "Too Little Too Late" by JoJo (2006)

Blackground

JoJo makes her way back on our list with “Too Little Too Late,” a song that’s essentially the precursor to “Leave (Get Out).” The gist of it is, JoJo doesn’t give second chances, and neither should you.

97 | "Single Ladies (Put a Ring On It)" by Beyoncé (2008)

Columbia

Beyoncé sings a song about being a newly single lady. Need we say more?

98 | "I’d Rather Go Blind" by Etta James (1968)

Universal Music

Etta James tackles relationship woes in her 1968 hit “I’d Rather Go Blind.” Honestly, we could listen to James sing just about anything and love it, but this is a particularly powerful piece from the legendary artist.

99 | "Stay With Me" by Sam Smith (2014)

Capitol

Sam Smith returns to our list with “Stay With Me,” a breakout hit from the artist that solidified their place on the map. This tune’s a sad one, with Smith acknowledging in the chorus that “this ain’t love, it’s clear to see.” Either way, Smith’s soulful sound is a cure-all.

100 | "Love Song" by Sara Bareilles (2007)

Epic

Don’t let the title fool you: “Love Song” by Sara Bareilles is anything but. The artist tackles the experience of feeling conned by a relationship, singing, “I learned the hard way that they all say things you want to hear,” and, “You are not what I thought you were, hello to high and dry.” Sure, heartbreak stinks, but hearing Bareilles’ flowery voice articulate your feelings makes it a little easier to swallow.