The 25 best songs about breakups

When the great Roy Orbison sings, we should listen. Orbison had said the song was about knowing something is over before it's actually over — especially a relationship. It also happens to be one of Orbison's most beautiful songs.

One of the most recognized songs of all time, there are several versions out there, but Gaye's is the one that stands out among all. While the tune has that memorable soul sound, it's a gut-wrenching song about someone finding out that his lover is getting it on with somebody else. Ouch.

This is the song to play for anyone who has broken off a relationship around Christmas. Mitchell speaks of Christmas time, and legend tells that it could be about her moving on from the late 1960s/early-'70s relationship with Graham Nash. It's also one of the most covered of all Mitchell songs, notably by English pop star Ellie Goulding in 2019. 

Arguably the song that defined Simon's career and one whose backstory is among the most intriguing in music history. Who exactly is this self-indulgent boyfriend Simon thinks is "so vain?" Is it ex-lover Warren Beatty, whom Simon acknowledged that a verse in the famed cut is about? There's also speculation that it could be about Mick Jagger or prominent writer Nicholas Delbanco. 

In many circles, it's considered the greatest breakup tune of all time. The highlight of Fleetwood Mac's commercial breakout Rumours, the song was written from Lindsey Buckingham's point of view on his split with bandmate Stevie Nicks. It doesn't paint Nicks, or the situation, in a positive light, but it sure made for a great track that has stood well over time.

The B-side to "Go Your Own Way," "Silver Springs" is Stevie Nicks's take on her famous break-up with bandmate Lindsey Buckingham. Nicks is not as brutally straightforward as Buckingham was on "Go Your Own Way," but the song is haunting and lets Buckingham know he's giving up a good thing. 

This disco classic might be the most empowering post-breakup song of all time. More than 40 years after its release, the former No. 1 hit still has a place in pop culture — whether in movies, television, commercials, or karaoke. Though Gaynor had other hits, none experienced the level of success and iconic status as this moving-on anthem.

Some insight into the tortured soul that was Joy Division frontman Ian Curtis. The lyrics touch on Curtis' marital issues and what he was thinking through while also dealing with depression. Though it has that quintessential post-punk, synth-pop sound, the lyrics are haunting and take the listener into the mind of the talented but troubled Curtis. He committed suicıde one month before the release of Joy Division's biggest commercial hit. 

This was the last top-10 single the Swedish quartet earned in the United States. Though Björn Ulvaeus notes the song is about going through a divorce, he claims it is not specifically about the dissolving of marriage to bandmate Agnetha Fältskog. It's a beautifully sad pop song that the one-time couple had to perform together.

In addition to being down in the dumps from his recent breakup, Kihn isn't too happy that there aren't many good breakup songs for him to drown his sorrows in. So as some cathartic measure, Kihn decides to sing about the latter and essentially come up with his own severely underrated breakup song. Genius. 

It's never easy trying to get your ex to come back, knowing that's not going to happen for whatever reason. That's what Collins was singing about on his '80s hit that was part of the Against All Odds soundtrack. It's a song about feeling hopelessly in love, which can be painful even for a stud like Jeff Bridges.

O'Connor became a household name on the pop scene with her work on this Prince-penned heartbreak ballad about a jilted lover unsuccessfully trying to move on from being dumped. The poignantly powerful music video, where the crew-cut O'Connor sheds some tears, only added to the song's emotional impact that defined her career.

With one hit, Canada's Morissette went from a national pop star performing in shopping malls to the most angst-ridden female voice of the 1990s. Or least on one track. To say this breakup was messy would be a severe understatement, and Alanis is not doing well and wants her ex to know. But who exactly is she shooting daggers at? Former Full House star Dave Coulier addressed it in July 2022. Joey Gladstone, really?

Re-worked several times, this No Doubt hit began as a love song and turned into one about singer Gwen Stefani's breakup with bassist Tony Kanal after seven years as a couple. It's never easy being in a band with someone you broke up with, but Stefani and Kanal made it work, and the song was honest and strong enough for the world to take this band seriously.

Even a multiple-Grammy winner like Braxton can feel heartbreak. She did not write this monster breakup ballad about begging a former lover to return and make things right, but she put all her emotion into performing it like a yearning ex. It should be recognized as one of the most powerful pop ballads of the 1990s. 

While JT reportedly has not come out and said this song is completely about his breakup with Britney Spears, he's stated it did inspire the writing of the song. The ballad about feeling down after some good love gone wrong is one of Timberlake's best songs and earned him tremendous success to jumpstart his stellar solo career.

Clarkson wasn't the first choice to perform the song (Pink and Hilary Duff were reportedly given the first crack), but the American Idol songbird more than did the power-pop ballad justice. A song about being glad to break free from a bad relationship remains one of Clarkson's signature tunes and among the best radio-friendly breakup songs of all time.

One of Beyoncé's biggest solo hits, "Irreplaceable" is a tale about the end of a relationship where the male half wasn't faithful. Whether part of Destiny's Child or on her own, Beyoncé is all about female empowerment, especially when it comes to her songs that also allow her vulnerabilities to show. It's one of the great breakup songs of the 2000s.

There's almost a cabaret-like feel to one of Winehouse's most popular songs, which Mark Ronson helped pen. The basis for the soulful number reportedly stems from the late singer's controversial significant other, Blake Fielder-Civil, taking off to be with an old girlfriend. As troubled as the late Winehouse was in real life, she was full of energy and confidence when singing about romantic despair.

Even hipsters aren't immune to a little relationship trouble. Bon Iver leader Justin Vernon wails about being in a relationship, seemingly, for the sake of being in a relationship that is not filled with much substance. Hey, it's better than being alone, and sometimes we just need somebody to make us feel important and wanted.

There's nothing worse than being in the same place where an ex is hanging out and having a good time with someone else. Robyn knows the feeling on her disco-influenced hit that offers some catchy dance-pop hooks. It's upbeat enough to soundtrack cleaning the house or washing the dishes while looking to shake that romantic funk. 

Adele was trying to come to grips with the end of a relationship, looking to move on while not harboring any ill will toward her significant other. That's a healthy approach but usually better said than done. Then again, singing about it might help, so throw Adele on and hope for the best.

Rarely do songs about breakups or exes seem like a rollicking good time, but Swift seems totally upbeat while continuously shunning a former boyfriend trying to get back together with her. For the guy in question, it's no fun, but Swift's monster hit is an unabashed example of feeling good about leaving the past behind and moving on. 

Sure, there are those who don't want to take a group like Little Mix seriously. But in the realm of breakup songs, this is one of the better ones. It's an anthem of sorts for those ready to move on from a failed relationship, assuring that the best is yet to come while not looking back. 

"New York" shows off the versatility of one Anne "St. Vincent" Clark," who sings about living in the same city as an ex-lover post-breakup. It's a simple song from a musical standpoint, and even with the melancholy vibe of the tune, we seem to think Ms. Clark will be OK because she happens to be a strong woman who is comfortable showing off her vulnerability.

Breakup songs tend be better when there's an entertaining backstory to the track. In this case, for Grande, it was released in the wake of her notorious parting with then-Saturday Night Live funny and former fiancé Pete Davidson. Of course, it also seems like an empowering tribute to several of the pop star's other relationships gone bad. Undeniably catching, the song has even earned an iconic status within the world of pop culture -- notably for the title. It was also Grande's first single to reach No. 1 on the Billboard Hot 100, and was nominated for five MTV Video Music Awards. 

The massively popular "Driver's License" was the most-streamed song on Spotify for 2021. Not a bad way to break onto the mainstream music scene. Rodrigo's debut single is a power-pop ballad about dealing with heartbreak. She might be young, but heartache from a failed relationship hurts just the same for those of any age. It also showed a true mature side of a fledging artist, who co-wrote the tune with the versatile Dan Nigro, who also produced the tune. "Drivers License" won three of the Grammy Awards (Best Pop Solo Performance) that it earned a nomination. 

A special breakup tune should be like a roller coaster for the heart, soul. And, when it comes to the listener, the ears. Eilish certainly hits the mark with one of her most popular tunes. It starts out slow, showcasing Eilish's intoxicating bluesy voice. Then kicks up to a neo-EMO level that truly details Eilish's anger with a recent love. It's easy to say one is in control in the aftermath of a breakup, but really, there needs to be an outlet to unleash all that emotional rage and pain. The song peaked at No. 11 on the Billboard Hot 100, and was nominated for four Grammy Awards.

Sure, it might seem like today's pop breakup songs are a dime a dozen when it comes to what's out there. There are plenty that fit the mold in what we hear from Mendes on "When You're Gone." Poppy, up-tempo, polished and superbly produced. However, when it comes to pop bombast, this is truly one of the better efforts within the category. An easy sing-a-long tune, and one of Mendes's live highlights. It's never easy to move on from a breakup, but having a top 40 hit helps. Or, at least having a song like this to help get through the pain.

Sure, Taylor Swift might be queen of the breakup songs, but Miley can definitely hold her own with anybody. "Flowers" is her most recent gem from that category. Soulful, yet poppy at the same time. A pop-dance hit with an obvious flare for empowerment. Anybody who needs to have that fact reinforced, need only check out the music video for the song. There's a sense of confidence that Cyrus give off with "Flowers." And, naturally, she's earned massive success with the track. The single went No. 1 in more than 35 countries and is the most one-week streamed song on Spotify.