“Say Something” is just as dramatic and grief-stricken as the worst breakups feel in the moment. Listen here.

With her breakthrough track “I Miss You, I’m Sorry” paving the way, Gracie Abrams is steadily becoming the Gen Z queen of heartbreak songs. Listen here.

Matty Healy hits you right where it hurts on this one. Not wanting to be with your ex, but not wanting them to be with anyone else either? Ouch. Listen here.

“Lose You to Love Me” is a stunning tribute to emerging from a breakup stronger than you were before. Written on Valentine’s Day in 2019, this track marked Selena Gomez’s first ever Billboard Hot 100 No. 1. Listen here.

Lewis Capaldi’s pain seeped through every crack in his gut-wrenchingly raspy voice on this breakthrough single, which became the Scottish artist’s first ever Hot 100 No. 1. Even if it was about his grandmother, most listeners have applied the song to their ill-fated romances. Listen here.

It seems like most breakup songs focus on getting dumped, but Zucker and Cutler recognize how hard it can be to be the person who leaves on this devastating duet. Listen here.

Cheers to everyone reminding you of them, no one else coming close to comparing, and not ever being able to just “get over it.”

Sometimes, relationships definitely do not end on good terms. If you’ve ever had an ex talk trash about you after you called it quits, this standout single on Conan Gray’s Kid Krow is the song for you. Listen here.

“Glimpse Of Us” is a certifiably epic breakup song. Singing over stripped back piano about pining for your ex after moving on with someone else, Joji found his first ever Hot 100 top 10 hit in 2022 with this emotional rollercoaster of a ballad. Listen here.

Drunk texting isn’t a good idea, even if you’re Drake. Listen here.

Debilitating epilepsy and his own infidelity were ruining Ian Curtis’ life when he wrote the harrowing words to “Love Will Tear Us Apart,” now seen as one of indie rock’s most lasting statements. The single was released three months after his suicide in March 1980 and its title was inscribed on his tombstone. Listen here.

Filled with financial metaphors, Funkadelic’s head-bopping Maggot Brain track is a cautionary tale about falling for the tricks of someone with “insufficient funds” in the love department. Listen here.

One of five tracks on King Princess’ breakout project Make My Bed, “Talia” is the WLW heartache song to end all WLW heartache songs.

In true Elvis fashion, the icon’s mournful croon made this song — previously recorded by Brenda Lee — a hit on Hot Country Songs, reaching No. 16 in 1972. Listen here.

The message and hook of this Sedaka classic are so straightforward that they’re reassuring — no matter how hairy and complicated a breakup is, we can all take comfort in the fact that splitting up is hard for everyone. Listen here.

What happens when you finally start realizing your ex mistreated, manipulated and took advantage of you the whole relationship? As Phoebe Bridgers expertly puts it, “emotional motion sickness.” Listen here.

Of all the post-breakup songs on this list, this is the one you listen to when you just need to rage. Listen here.

Kanye’s dark period brought us this career curveball — a sharp left turn from the euphoria of Graduation that changed the rap game forever. Aside from paving the way for Drake and Kid Cudi’s sensitive careers, Ye bared his soul and showed us how even the biggest egos can succumb to heartbreak. Listen here.

A standout single from Styles’ sophomore album Fine Line, “Falling” remains one of the boy band star’s most vulnerable songs to date.

“Pink Pony Club,” “Hot to Go!” and other upbeat dance tracks may have been the ones that made Chappell Roan a star in 2024, but the Missouri native proved that she’s also an expert sad-song writer on tracks like “Casual” — an unabashedly bitter ballad that proves that situationship breakups can be just as painful as ones where the relationship was more defined. Listen here.

James easily laid down the most piercing cover of this Great American Songbook staple. Listen here.

Released in 1994 on Grace, the only album Buckley made before his premature death, “Lover” is a breathtaking postmortem on a relationship the rocker clearly hoped would get resurrected one day. Listen here.

Listening to this song, it’s hard not to envision an overwrought heartbreak scene in some B-movie. Cheese factor aside, the sound of Nilsson’s voice blasting through this Grammy-winning Badfinger cover is the sound of someone who literally “can’t live anymore.” Listen here.

“One Less Bell to Answer” recognizes the specific pain of knowing you’re better off without someone, but still missing their presence. Listen here. 

“Need You Now” takes place in the aftermath of a breakup, in that horrible transition period where the only person who can comfort you is the reason you’re sad in the first place. Listen here.

“At 13, I didn’t even have my first kiss yet,” a 22-year-old Jojo told Billboard in 2013. “What the f–k was I talking about? ‘Get out’? Get out of where — my playground?” She’s grown older and wiser, but her 2004 hit is still a breakup playlist essential. Listen here.

Ronstadt’s 1974 take on “You’re No Good” is easily the most famous cover of the song, hitting No. 1 on the Hot 100. It brilliantly calls out a rotten ex while also acknowledging that those in glass castles maybe shouldn’t be throwing stones. Listen here.

Blige’s 1994 cover of Rose Royce’s original gets increasingly heart-wrenching from start to finish, with the Queen of Hip-Hop Soul going from spiraling about her breakup to fully pleading with her ex to take her back. Listen here.

If The All-American Rejects taught us anything, it’s that it can be okay to not wish someone well. Where’s your picket fence, love? Listen here.

The whisper-soft first half of the title track to Eilish’s second studio album is definitely good, but the screaming, punk rock, unhindered catharsis, rip-your-ex’s-heart-out-and-spit-on-it second half? Greatness.

Sometimes, it’s the right person at the wrong time. Frank Ocean explores a tale of young romance that was doomed from the start on “Ivy,” reminding us that no one ever really forgets their first love. Listen here.

“Somebody That I Used to Know” had the world in a chokehold for weeks (eight weeks at No. 1, to be exact) not only because it’s incredibly catchy, but also because it addresses one of the rarely talked-about, hardest parts of any breakup: the shock of being lovers one moment and strangers the next. Listen here.

Dinah was one of countless singers to record this American Song Book classic, but her singular voice makes her version arguably the most comforting. Listen here.

When you would’ve done anything for a person and they still walked away? That’s a hurt only Paramore can remedy. Listen here.

Whether it’s been weeks, months or years, “Stick Season” is a requiem for everyone who’s still. Not. Over it. Listen here.

SZA’s first No. 2 single, “Kill Bill,” is the standout single from her critically-acclaimed album SOS (which, for the record, is chock-full of excellent breakup songs). It finds the R&B/pop star shamelessly living out a fantasy many of us have had at some point, if we’re honest with ourselves: murdering an ex in cold blood. Listen here.

Heap’s musical pinnacle feels like a fever dream, as do the most crushing breakups. Listen here.

Brad Paisley and Allison Krauss’ iconic 2000s country duet is a fragile story about two people who take a breakup to the ultimate extreme. Listen here.

Like many of the songs on The Boss’ 1987 record Tunnel of Love, “Brilliant Disguise” — all about the loneliness of realizing you don’t recognize your partner as the person you fell in love with anymore – is believed to be about his then-deteriorating marriage to his ex-wife, actress Julianne Phillips. Listen here.

Rumor has it Ms. Swift wrote this song to spite a pop music-hating ex-boyfriend, even going so far as to deliberately pen a main hook that’s so contagious, you can’t get it out of your head no matter how hard you try. And if that was, in fact, the intention — congratulations to Taylor on a job well done.

This cinematic classic from The Way We Were starring Streisand and Robert Redford could be the national anthem for a country called “Right Person, Wrong Time.” Listen here.

“When I Was Your Man” doubled as an apology letter to all the ladies who haven’t been treated right by their partners, as well as a warning call to all the men who don’t prioritize what’s most important. Thank you, Bruno Mars. Listen here.

When it first dropped in 2013, “Wrecking Ball” was most buzzworthy for its music video – in which Miley Cyrus famously poses naked on a literal wrecking ball – and the fact that it seemed to be about the star’s breakup from Liam Hemsworth. Years later, the Hot 100 No. 1 hit has endured as one of the most passionate, cathartic breakup ballads of its decade, thanks to Cyrus’ raw vocals and powerhouse chorus. Listen here.

Before it was sampled in Puff Daddy and Faith Evans’ Biggie tribute “I’ll Be Missing You,” Andy Summers’ immortal guitar line soundtracked one of the ’80s biggest soft rock jams (both songs went No. 1 on the Hot 100). It’s a stirring tale of post break-up devotion… perhaps a little too much devotion, considering Sting admitted its undertones of control and surveillance. Listen here.

To the left, to the left. This 2006 Bey banger remains one of her most take-no-sh-t, give-no-f–ks songs ever — and that’s saying something. Listen here.

Released just after Grande’s highly publicized breakup from SNL‘s Pete Davidson, “Thank U, Next” was as much of a cultural reset as any one song can be. It reimagined how one can look back on their past, failed relationships — with an appreciation for the lessons learned in place of bitterness — all while earning the pop star her first ever Hot 100 No. 1.

Orbison didn’t actually cry in the recording booth, but the way he runs through the titular word in this Hot 100 No. 2 hit from 1961 gives you all you need. Listen here.

What’s more difficult, the actual breakup or the act of moving on? Patsy Cline makes a good case for the latter. Listen here.

“There’ll be good times again for me and you/ But we just can’t stay together, don’t you feel it, too?/ Still I’m glad for what we had and how I once loved you.” Sad but hopeful, real and raw, King gives a masterclass on dealing with the end of a relationship with a healthy mindset. Listen here.

Lots of people dream about being someone’s “the one that got away,” but Katy Perry’s hit single (No. 3 on the Hot 100) of the same name reveals that it’s not all it’s cracked up to be. Listen here.

Fury seeps through every word on Lucy Dacus’ immaculate soft rock track “Night Shift,” on which she charts the course for her own healing – including how she plans on avoiding her ex. And toward the end, she fantasizes over a comforting thought: “In five years, I hope the songs feel like covers/ Dedicated to new lovers.” Listen here.

With her breakout, Hot 100-topping single, Lizzo reminded everyone that there’s nothing wrong with knowing you’re too good for someone.

Joe Jackson’s mid-tempo 1980s jewel examines the simple but devastating math behind breakups: something that was once a “1” splitting into 2. Listen here.

Even in her early days with The Supremes, Diana Ross’ passion couldn’t be denied. “You Keep Me Hangin’ On” is one of the most desperate, impassioned Motown songs you’ll hear, so it’s no surprise it grew with the times. After the Supremes took it to No. 1 on the Hot 100 in 1966, Vanilla Fudge’s psychedelic, sludgy cover took it to No. 6 in 1968; in 1987, Kim Wilde brought it back to the top of the Hot 100 with her version. Listen here.

Raitt paints a vivid picture of the final hours between two people on very different pages regarding their relationship. Side effects may include: lots and lots of tears. Listen here.

Even when you feel like falling apart, Warwick’s timeless hit will help you keep it moving. Listen here.

Mournful, sullen and devastating, Leonard Cohen’s world-famous lyrical masterpiece is one of the most-covered songs of all time. Listen here.

When being in a relationship makes you feel lonelier than if you were on your own, queue up this one from Natalie Imbruglia. She gets it. Listen here.

Rumored to be about famous ex Katy Perry, John Mayer’s funk-infused soft rock track “Still Feel Like Your Man” examines how your whole identity changes after a breakup – and how hard it can be to shake your past duties as someone else’s partner. Listen here.

Breakups signify an end, but they also mark the start of a lot of big questions about where both parties go from here. Tyler, the Creator examines one of the most challenging queries ex couples must often face – where do we stand now? Listen here.

One of Garth Brooks’ signature songs, “The Dance” can be interpreted a few different ways, but for many, it represents how breakups – and falling in love in the first place – are, in so many ways, “left to chance.” It’s a thought that can be both infuriating and comforting, or both. Listen here.

Even if you’re not breaking up with another member of your internationally famous rock band, it’s easy to get behind “Go Your Own Way” — which conveniently doubles as a great running song (just ask Forrest Gump). Listen here.

Al Green’s Bee Gees cover is soulful and haunting, repeatedly asking the one question everyone who’s gone through a breakup has had to ask themselves at one point: how can you mend a broken heart? It takes time and it’s different for everyone – but Mr. Green is here for you in the meantime. Listen here.

O’Connor scored her first and only No. 1 hit on the Billboard Hot 100 — where she stayed for four weeks — with her haunting take on Prince’s “Nothing Compares 2 U.” Listen here.

Just after the love-at-first-sight giddiness of “I’ve Just Seen a Face,” The Beatles’ Help! (U.K. version) hits you with the heartbreak of “Yesterday.” Paul McCartney’s two-minute acoustic confession proves just how quickly emotions can shift, even on a track listing. Listen here.

Phil Collins’ “Against All Odds” — written for the 1984 Taylor Hackford film of the same name – topped the Hot 100 for three weeks with its poetic lyrics about feeling totally empty without a lost love. Listen here.

Rod Stewart empowers listeners to walk away from a partner – who, in his case, is implied to be an inappropriately older woman – when that person has “made a first-class fool” out of them. That said, Maggie May’s powers are a little to overwhelming, and Stewart admits during one of the final choruses: “I couldn’t leave you if I tried.” Listen here.

The combined pain of saying goodbye to a relationship and reconciling yourself to the mistakes you made isn’t an easy thing to capture in just one song, but Lorde is no ordinary songwriter. Her sophomore album Melodrama is filled with nuanced notes on rediscovering and reclaiming yourself after a breakup, from “Green Light” to “Liability” — but there’s just something special about “Supercut” that’s made it a time-tested fan favorite in particular. Listen here.

Morrissey’s heartbreaking croon walks the line between knowing a relationship is dead but clinging to its remains anyway, completely at a loss for what to do next. Listen here.

Come on, you knew this song would be on here. Rodrigo’s debut single reigned the Hot 100 for eight weeks in 2021 thanks to its show-stopping bridge and all too relatable lyrics about still being in love with the person who dumped you for someone else.

Bill Withers ‘70s hit is simple but profound poetry about feeling all the warmth drain from your life when a lover leaves you behind. Listen here.

George Strait’s deceptively uptempo 1980s hit pays homage to one of mankind’s most tried-and-true activities to do after getting dumped: heading over to your local bar and getting sloshed. Listen here.

As Zach Bryan and Kacey Musgraves prove on their Hot 100-topping duet, sometimes it’s not the breakup itself, but the memories that linger that are the most painful part of a split. Listen here.

Does your partner never buy you nothin’? Are they always bringing their friends around instead of hanging out with you one-on-one? Those are both signs it’s time to kick ‘em to the curb, per Erykah Badu’s infallible logic. Listen here.

One of Motown’s signature staples, “The Tracks of My Tears” captures the difficult, all-too-relatable human experience of having to mask heartbreak just to get through everyday life – and sometimes failing to do so. Listen here.

Ever need a song to get hyped before breaking it off with someone who doesn’t deserve you? *NSYNC will give you the courage to say bye, bye, bye. Listen here.

This Lionel Richie-penned Commodores hit makes walking away sound exactly as its title suggests: easy. If someone’s not right anymore, it can be okay to just stroll right out of their lives. Listen here.

The end of the Justin-Britney relationship coalesced in the start of the Justin-Timbaland connection, and we can’t argue with the results. Ice-cold sarcastic shade rolls off JT’s tongue over studio work from Timb that hints at the wonders of the years to come. Listen here.

No Doubt’s signature 1995 hit nails the anxiety of the moments leading right up to a breakup when both parties know what’s about to happen but just can’t bring themselves to say the words. Listen here.

Unlike many of the songs on this list, this one isn’t bitter, or even sarcastic. Adele’s anthem to taking the high road — despite the heartbreak it entails — is one of the truest ballads the 2010s gave us. Listen here.

“Climax,” “U Don’t Have to Call” — there are plenty of Usher songs we could have picked for this list, but this Confessions slow jam (which topped the Hot 100 for eight weeks) just hits the hardest. In the chorus, he pledges to let the breakup run its course, but by the next verse, wonders what it’ll take to get his shorty back. Love is confusing. Listen here.

Toni’s timeless slab of emotion over a luscious R&B beat earned her 11 weeks atop the Billboard Hot 100 in 1996 and 1997.

Who is this song about? Mick Jagger? Warren Beatty? Simon’s never told us for sure, but that’s probably helped this song’s legend grow. Who doesn’t know someone that could fit the “so vain” bill? Okay, maybe not the parts about the Learjet and the yacht. Listen here.

Boyz II Men spent a then-record-breaking 13-week run at No. 1 on the Hot 100 with “End of the Road” in 1992, and for good reason. The R&B group’s buttery group vocals nail the “unnatural” post-breakup feeling of being apart from someone who still feels painfully familiar to you. Listen here.

Part Christmas song, part breakup song, full-on masterpiece. Listen here.

Some breakups are just one of many with the same person over and over again, a difficult – and usually toxic – cycle that Lauryn Hill grapples with on her iconic The Miseducation of Lauryn Hill classic. Listen here.

“Landslide” is technically a Fleetwood Mac song, but all credit goes to Stevie Nicks’ stunning, soul-shaking lyricism about forging ahead in the face of utter heartbreak. Listen here.

Swift’s 2022 ten-minute track serves as an extended version of the original one she released in 2012, meaning five extra minutes’ worth of searing, specific details of her and her ex’s crash-and-burn relationship were brought to light 10 years after the fact. It’s a lyrical masterpiece that scored the pop star the record for the longest song to go No. 1 on the Hot 100.

“We Belong Together” is one of Mariah Carey’s many, many Hot 100 No. 1s (19 to be exact), but with lyrics like “Who am I gon’ lean on when times get rough? / Who’s gon’ to talk to me ’til the sun comes up?,” few of them are as heartbreaking. Listen here.

There’s a reason this track has stuck with people so profoundly ever since it came out in 2010. Few other artists have so masterfully blended pulsing dance club beats with the total, utter devastation of watching someone you still love move on to someone else. Listen here.

Heavily rumored to be about Bob Dylan’s famous split from Suze Rotolo, “Don’t Think Twice, It’s All Right” finds its narrator at a place of complete, aspirational indifference over a partner who simply “wasted [his] precious time.” No need to think twice about it – just keep freewheelin’ forward. Listen here.

One of Winehouse’s most celebrated songs with frequent collaborator Mark Ronson, “Back To Black” was able to capture the specific, blackhole type of hurt that comes when you fall back to your vices to comfort you after a breakup. Listen here.

There had been plenty of breakup songs before Alanis, but few female artists in the mainstream really went there like she did here. Mr. Duplicity is still feeling the burn. Listen here.

In addition to being one of Houston’s most stunning vocal performances, “I Have Nothing” is the epitome of continuing to fight for something long after it’s already over.

Prince’s apocalyptic magnum opus brilliantly and passionately rolls so many emotions – regret, relief, the peace that comes with knowing something better is around the corner — into one timeless song. It’s time we all reach out for something new: That means you, too. Listen here.

Inspired by Yeah Yeah Yeahs’ “Maps,” Kelly Clarkson’s anthemic breakup rocker hit No. 2 on the Hot 100. Listen here.

“I Want You Back” is one of The Jackson 5’s first and biggest hits. It’s a lighthearted reminder that sometimes, we’re the ones in the wrong when it comes to a breakup — and any heartache can be soothed with a little dancing. Listen here.

A “Since U Been Gone” for an earlier generation, “I Will Survive” was a women’s strength anthem for the disco era. Really though, this track would have been pure fire in any generation. Listen here.

Two decades before Whitney Houston’s Bodyguard rendition brought it back into the spotlight (and to the top of the Hot 100), Dolly wrote and performed this sentimental standard about her professional split from Porter Wagoner, the country legend who discovered her (Parton later performed the song in the 1982 movie musical The Best Little Whorehouse in Texas). She’s well known for her sassy sense of humor, but Dolly’s got heart, too — and this song took her to the top of Hot Country Songs in 1974 and 1982. Listen here.