The 20 Best Breakup Songs Ever—and Who They're About

Carrie Underwood's "Before He Cheats" is turning 15, so we're celebrating by grabbing our keys and Louisville slugger and looking back on the best breakup anthems of all-time.

By Tierney Bricker Aug 19, 2021 10:46 AMTags
Watch: Carrie Underwood Shares Throwback Pics for 10th Anniversary

Can you believe it's been 15 years since Carrie Underwood took a Louisville slugger to both headlights of an unnamed ex's pretty little souped-up four-wheel drive and slashed a hole in all four tires?

The country superstar released "Before He Cheats" on Aug. 19, 2006 and it quickly became one of her most popular songs ever. It spent five weeks atop the Billboard Hot Country Songs chart, crossed over onto the Top 40 Mainstream list and spent a whopping 64 consecutive weeks on the Billboard Hot 100, making it the sixth longest-charting single in the history of that category. Oh, and it won the Grammy for Best Female Country Vocal Performance and Best Country Song, and, of course, became an enduring breakup anthem for the ages.

But the song wasn't initially written with the American Idol winner in mind. 

"At the time, Gretchen Wilson was going in to record," songwriter Chris Tompkins recalled to The Boot. "After her first record, everybody wanted to have a song on that second record, and I was trying to think of edgy stuff. I never would've thought that Carrie Underwood would record it!"

Carrie Underwood and Mike Fisher's Cutest Photos

Initially, continued co-songwriter Josh Kear, "When we were writing it, we were actually trying to keep it humorous...but when Carrie got hold of it, she just did it so well and really made it her own. We expected it would be a little more lighthearted. But when we heard it, we thought, wow, she really drove it home! We couldn't be more grateful to Carrie for just wailin'!"

Same, man. Same. 

In honor of the 15th anniversary of "Before He Cheats" and us scream-singing, "That I dug my key into the side of his pretty little souped-up four-wheel drive," we're revisiting some of the best breakup songs ever. We're talking all those hits from Ariana Grande, Taylor Swift and The Weeknd that let the musicians use their lyrics as a way to spill the tea on their love stories without really getting any teardrops on their guitars.

Ariana Grande's "Thank U, Next"

After a fast-paced romance and high-profile split with Pete Davidson, Grande decided to throw all subtly and veiled references out the window for the first song she released post-breakup. Her former fiancé isn't the only ex name-checked in the song, with Ricky AlvarezMac Miller and Big Sean also earning shouts in the named in the empowering single. 

Before its release in 2018, Grande tweeted that the song was "the opposite" of a "diss track" and she wasn't kidding. "Thank u, next" is all about Ari's new relationship with herself after learning valuable lessons from all of her past romances.

"One taught me love / One taught me patience / One taught me pain / Now, I'm so amazing / I've loved and I've lost," she sings...and now we bet you can't get that out of your head. 

Kelly Clarkson's "Since U Been Gone"

"But since you been gone...I can breathe for the first time..."

It's hard to imagine anyone else singing what is arguably The Voice coach's best song, but it almost went to Pink, who turned it down, and then Hilary Duff, who also passed. So, Clarkson ended up releasing it as the first single off of her 2004 album, Breakaway. (No, Clarkson didn't write the catchy tune, Max Martin and Dr. Luke did.)

"Since U Been Gone" quickly became the post-breakup relief anthem for a generation, even making its way onto MTV's Laguna Beach and in Pitch Perfect. Better yet, it earned Clarkson the Grammy for Best Female Pop Vocal Performance. 

Beyoncé's Lemonade

Come on, how does one pick just one song off of Queen Bey's iconic 2016 album? Sure, she stayed with Jay-Z, but she held nothing back...exposing his wrongdoings, revealing intimate details about their marital struggles, using the album as a diary and a warning simultaneously. It is a work of art and a work of love and pain and hope, making it far more than just a break-up album. 

Justin Timberlake's "Cry Me a River"

Though he's never actually said directly that his 2002 hit is about ex-girlfriend Britney's totally about Britney Spears, with a look-alike even cast for the music video.

"I've been scorned. I've been pissed off," he wrote of the inspiration for the anthem in his new book, Hindsight: & All the Things I Can't See in Front of Me. "I wrote 'Cry Me a River' in two hours. I didn't plan on writing it."

The song was a critical and commercial smash hit for Timberlake, who was establishing himself as a solo artist after N Sync. It worked—the scornful song won the Grammy for Best Pop Male Vocal Performance.

However, Timberlake issued a belated apology to Spears in in the wake of February's The New York Times Presents 'Framing Britney Spears' for seemingly laying the blame for their split at her feet.

Taylor Swift's "Dear John"

Do you know how hard it is to highlight Swift's best breakup song when she is basically the godmother of breakup songs, knowing exactly which crumbs of info will turn her listeners into detectives? Her albums are her journals and her songs are her relationship guides. But her most obvious one was "Dear John" off of her 2010 album Speak Now.

Sample lyric? "Dear John, I see it all, now it was wrong / Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?"

 It was, of course, about John Mayer, though Swift never confirmed it...but Mayer decided to a few years later, admitting in an interview that the song "humiliated."

"It made me feel terrible," Mayer told  Rolling Stone. "Because I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do." He felt the move was "cheap songwriting" to, as he described it, "rub your hands together and go, 'Wait till he gets a load of this!'"

Swift's response? "How presumptuous!" 

Carrie Underwood's "Before He Cheats"

Lesson learned from this revenge ballad? Do. Not. Cross. Carrie. Underwood.

While she charmed American Idol viewers with her sunny disposition and country crooning, fans were introduced to a new whole side of the singer when she released "Before He Cheats" and took a Louisville Slugger to both headlights. 

The single was once the the best-selling country song of all-time and won Underwood two Grammys in 2008 (Country Song of the Year and Best Female Country Vocal Performance). And, more importantly, it (hopefully) inspired some cheaters to think next time before they...well, you already know...

Olivia Rodrigo's "Good 4 U"

"Like a damn sociopath!"

Talk about knowing how to deliver teen angst! The High School Musical: The Musical: The Series star proved she was far from a one hit wonder following the record-breaking success of her debut single "Driver's License" when she released this irresistibly emo track.

A second No. 1 release? You're doing great out there without him, baby. (The him in question is reportedly her HSM co-star Joshua Bassett.)

Justin Bieber's "Love Yourself"

Many songs have been born from the rollercoaster relationship that was Jelena, but arguably the most bitter one from Bieber is "Love Yourself," which suggest Justin's mom Patti Mallette wasn't Selena Gomez's biggest fan. ("My mama don't like you—and she likes everyone," he sings in the chorus).

 Many believed the song title was a direct reference to Gomez and a tattoo she has on her back, which is the Arabic translation of the phrase "Love Yourself First."

However, it turns out Bieber didn't even write this song...Ed Sheeran did. Sooooo…sorry Beliebers!

Selena Gomez's "Love Will Remember"

The first of many songs about her relationship with Bieber, Gomez decided to start this 2013 single with an actual voicemail from her ex. 

"Hey babe, it's me," Bieber says in the voicemail. "I just want to call and tell you that I love you so, so, so, so much. I just wanted to let you know that you are my princess. You are worthy of all the love in the world. You are the love of my life."

At the time, a source close to Bieber told us he was "blown away" by the track. Five more years of on-and-off dating confirms that!

The Weeknd's "Call Out My Name"

The Weeknd's 2017 hit song was all about his failed relationship with Selena Gomez, with apparent references about her kidney transplant, as well as her reconciliation with ex Bieber shortly after their split in October 2017.  

"Guess I was just another pit stop 'til you made up your mind," The Weeknd sings during the song. Damn...

Charlie Puth and Selena Gomez's "We Don't Talk Anymore"

Surprise, another song alluding to Gomez's on-and-off romance with Bieber! In 2018, Puth fully admitted that their 2016 duet was about his and Gomez's short-lived romance coming to an end because of her ex.

"It's about a particular moment in my life, when someone very close to me wanted the attention of somebody else," he explained to Billboard. "When I found that out and we ended it, I might have done some shady things too, and she might have asked me, 'How long has this been going on?'"

He then added, "I don't kiss and tell, but the only way a song like that can come across as real is if there's something else going on behind the scenes. And that's what was happening [with Gomez]. Very short-lived, very small, but very impactful. And it really messed me up. I'm trying to put this the best way possible: It wasn't like I was the only person on her mind. And I think I knew that going in—what I was getting myself into."

Drake's "Marvin's Room"

The rapper's 2011 track is Drake at his emo best...and perfectly capturing the phenomenon of "drunk dialing," as Drake calls an ex from a nightclub. (Said ex allegedly sued him after the track was released. Take care, Drake!) Definitely one of his best songs ever.

Nick Jonas and Miley Cyrus' "Before the Storm"

It's rare that a couple gets together to record a song after their split, but that's what these two did in 2009 several months after ending their thee-year on-off romance for good.

At the time, Jonas told MTV News that the bittersweet ballad was "probably one of his favorite songs because it has a great story to it." Though it didn't initially include Cyrus, Jonas thought it would a good song to record with his ex and share with their young fans. #Niley4ever. Curiously enough, they performed the song on stage together amid reconciliation rumors...right before Cyrus met Liam Hemsworth on the set of The Last Song

But both Jonas and Cyrus have released other songs about their break-up(s): Cyrus' 2008 hit "7 Things" is all about Jonas, while he revealed in 2017 that the Jonas Brothers' 2013 songs hit "Wedding Bells" was penner after Cyrus got engaged to Hemsworth. 

Christina Aguilera's "Fighter"

If this jam hasn't been on your workout playlist since it came out in 2003, you've been living your life wrong for over 16 years. Sorry not sorry!

While the singer never revealed who the empowering track was about, she did say on RuPaul's Drag Race's after-show Untucked that "he deserved it."

Alanis Morissette's "You Oughta Know"

The. Gold. Standard. Of. Breakup. Songs.

Morissette's 1995 hit taught us hell hath no fury like a talented songwriter scorned. "You Oughta Know" also delivered one of the most epic celeb urban legends: It's about Full House's Dave Coulier. Uncle Joey, what did you do?!

"There was a lot of familiar stuff because she was writing a lot of material when we were dating, so there were some familiarities all throughout [her album] Jagged Little Pill," Coulier told HuffPost Live in 2014. "The one that got me was, 'I hate to bug you in the middle of dinner.' That was because we had already broken up and she had called—she was living in Canada at the time—she called, and I said, 'Hey, I'm right in the middle of dinner, can I just call you right back?' I remember that line when I heard 'You Oughta Know,' and I just was like, 'Uh-oh.'"

Ed Sheeran's "Don't"

Like his friend Taylor Swift, Sheeran is very good at delivering some gossipy goods in his songs, and "Don't" definitely did. The 2013 song was about his ex Ellie Goulding allegedly cheating on him with One Direction's Niall Horan while on tour, Sheeran later telling Entertainment Weekly,  "I had to be as honest as possible in that song because otherwise what's the f–king point? There'd be no anger or pain in that song if it was just very sweet and nice."

Pink's "So What"

Written during a separation from her husband Carey Hart in 2008, Pink's "So What" is a little petty and a lot of fun, with lines like "You're a tool" and "I'm not gonna pay his rent." 

Pink even got her then-ex to appear in the music video, though she didn't tell him what the song was about before filming. "He hadn't heard the song before he showed up for the video," she told Radio 1. "He's a good sport, he knows how psychotic I am, he spent six-and-a-half years with me. A year with me is like dog years."

After they reconciled in 2009, Pink talked about still performing the song when she appeared on Ellen that year: "It's funny now!"

Nick Lachey's "What's Left of Me"

The 98 Degrees lead singer released this solo track in 2006 following his very public divorce from Jessica Simpson, and it ultimately became his most successful song.

Ironically enough, then MTV VJ Vanessa Minnillo would take on the role of Simpson in the music video, with Lachey later going on to marry her in 2011. 

Katy Perry's "Roar"

Sure, there are more obvious breakup songs from the American Idol judge, but "Roar" is her most uplifting and came at a pivotal point in the singer's life during one of the off-periods of her on-and-off romance with John Mayer. Yep, the musician is making his second appearance on this hallowed list. 

"Roar is a song I wrote as I was a little bit upset," she told Radio 1 in 2013. "I found myself having a break with my boyfriend, who I loved very much and it really hurt my heart. I said to myself, 'I need to see what is going on with me and make sure I'm all good.' When you break up with someone it's easy to say they are crazy and think it's all them, but, honestly, maybe there is 50 percent responsibility on your behalf. It was just time for me to be honest with myself."

No Doubt's "Don't Speak"

Imagine being in a band with your ex? That was a reality for Gwen Stefani, who wrote a song (along with her brother and No Doubt co-founder Eric Stefani) in 1996 about her breakup with bassist Tony Kanal. Awkward? Yep! Worth it? Duh. 

"It's still weird. Even last night when I sang the song it's still weird," she said on The Howard Stern Show in 2016. "I just rolled my eyes and walked away [like] really? You're still feeling that?"

(Originally published Tuesday, November 6, 2018 at 12:33 p.m. PT)