50 Heartbreak Songs That Hurt in the Best Possible Way

A song is one of the best ways to console yourself after a breakup. Heartbreak songs are kind of the Universal Translator of Breakup Pain. They take the stings of breakups, unrequited love, or broken promises and turn it into an expression of sound that seems almost therapeutic. There’s something therapeutic in screaming out a chorus that captures how you feel or shedding a tear on a soulful ballad. They’re painful in the best kind of way, making you not feel alone.

There’s a list of 50 breakup songs that can be found below. From classic soul ballads to modern pop hits, all of these songs are sure to touch a chord as they capture the raw emotion of a breakup. If it’s a new breakup or an old one, this song is there to help you wallow in it.

Someone Like You by Adele

The soulful ballad by the singer from the year 2011 was a global anthem of breaking hearts. The song was written by the singer after a split. It’s basically the raw emotion of hoping all is well with the ex, despite the ache in the heart. The song reached number one globally.

Nothing Compares 2 U by Sinead O’Connor

There aren’t many songs which evoke the pain of a breakup as effectively as this classic of 1990. The song was written by Prince, but it was given a hauntingly beautiful rendering by Sinead O’Connor. The song, along with its famous tear-filled video, was a global phenomena, reaching the top of the charts in many countries. It’s the definitive song for those empty emotions after an breakup.

I Will Always Love You by Whitney Houston

Whitney Houston’s epic cover of Dolly Parton’s ballad has become an iconic anthem of heartbreak ever since its release in 1992, topping the charts globally as the soundtrack of The Bodyguard. The song, sung with Whitney Houston’s signature soaring vocals, captures the bittersweet feeling of saying goodbye while promising an endless love. The song is an anthem for all those coping with letting go of the ones they love.

Back to Black by Amy Winehouse

Amy Winehouse poured her troubled emotions into this classic song from the year 2006. Back to Black features her delivering lyrics that capture her going into darkness after losing love. The song’s Motown sound contributes perfectly to the emotional experience of this song. Back to Black stands not only as one of Amy’s best pieces of work, but it can also be referred to as a modern classic.

Yesterday by The Beatles

The Beatles’ classic from 1965 is the essence of the sorrow of a breakup. Paul McCartney’s lyrics of lost love struck true in everyone’s soul through this acoustic song. The song yesterday reached the top of the US chart and has been recorded by more artists than most other songs in history. Yet, after all these years, its regretful feel continues to be as relatable.

Love Will Tear Us Apart by Joy Division

This classic 1980 post-punk anthem shows that a broken heart crosses boundaries of musical genres. This song was written by Joy Division’s singer Ian Curtis as his own marriage was disintegrating. The painful emotions shine through the catchy tune. Written just before singer Ian Curtis’s premature death, this song became the most famous of Joy Division’s hits. Love Will Tear Us Apart still serves as an apt motto on the agony of a bad love.

Drivers License by Olivia Rodrigo

Olivia Rodrigo’s first single, released in 2021, was the Bea-Archiyana of breakup songs. The then-17-year-old Rodrigo breaks her heart on ‘Drivers License’ as she croons how she still drives by her ex’s road through her tears. The raw emotion of this song was relatable not only among Olivia’s age group but among all generations. The song’s raw emotion, accompanied by its piano tune, broke all streaming records and topped the chart worldwide.

Un-Break My Heart by Toni Braxton

Toni Braxton delivered one of the ’90s most powerful ballads in 1996. In Un-Break My Heart, she pleads for her lover to return and take away the pain. Braxton’s deep, sultry voice and the song’s dramatic melody struck a chord – it spent 11 weeks at #1 on the charts. Even today, its desperate chorus can make anyone misty-eyed.

Go Your Own Way by Fleetwood Mac

Lindsey Buckingham wrote Go Your Own Way in 1977 about his split with Stevie Nicks, and that tension fuels this classic rock song. Its driving beat and fiery guitars carry lyrics full of hurt and frustration. The track became a Top 10 hit and an enduring breakup anthem, proving that sometimes letting go rocks just as hard.

Dancing On My Own by Robyn

Robyn’s electro-pop track from 2010 is a celebration of a break-up. However, it’s still a tearful experience on the dance floor. The song ‘Dancing on My Own’ talks of an ex-lover moving on, with the agony of moving on from an ex relieved by dancing through the streaming of tears. The song was never a chart-topper, though it’s a classic song of this millennium – it’s the anthem of weeps on the dance floor.

You’ve Lost That Lovin’ Feelin’ by The Righteous Brothers

This soulful pop classic from 1964 presents an agonizing depiction of an eluding love. The Righteous Brothers make an impassioned appeal to rediscover a love that has been lost. The recording was created with Wall of Sound production by Phil Spector. The song presents an indelible mood of yearning. ‘You’ve Lost That Lovin’ Feelin” reached number one on the chart and was declared one of the most performed tracks of the 20th century.

I Can’t Make You Love Me by Bonnie Raitt

This ballad from 1991 is like a midnight confessional. The song captures the agony of unrequited love – the agony of recognizing that you can’t make someone love you. The song was not a chart-topper, but it’s been considered a classic ever since and often picked as one of the most sorrowful pieces of ‘beautiful sorrow.’

All Too Well by Taylor Swift

Taylor Swift’s storytelling skills come alive in ‘All Too Well’. Originally an album track in 2012, it was later followed by a 10-minute version of the song in 2021 that broke multiple charts. The song comes across like a diary written after the breakup, with memories, regret, and love still there. The lyrics of this song hit home hard for someone going through memories of a lost relationship.

Don’t Speak by No Doubt

No Doubt’s hit single from 1996, Don’t Speak, was inspired by Gwen’s actual experience of breaking up with her band’s bassist. The emotional depth of this song, from Gwen’s pleading vocals to its sorrowful tune, can be bested only by its global relevance, which helped it top the charts across countries. Even after all these years, this song has been the go-to rock ballad for ‘unspoken words’ after an split.

You Oughta Know by Alanis Morissette

Heartbreak isn’t always about tears – sometimes it’s pure anger. Alanis Morissette’s 1995 breakout hit You Oughta Know channels the fury and betrayal of being tossed aside. With jagged guitars and Alanis’s fierce, no-holds-barred vocals, the song became an anthem for jilted lovers. It hit the Top 10 and proved that sometimes screaming out your pain can be empowering.

Irreplaceable by Beyoncé

Beyoncé turned heartbreak into empowerment with this 2006 megahit. In Irreplaceable, she reminds her ex that he’s easily replaced – to the left with his boxes. The song’s catchy acoustic R&B groove and confident lyrics had listeners worldwide singing along. It spent ten weeks at number one in the US.

Since U Been Gone by Kelly Clarkson

This 2004 pop-rock smash shows that breakups can be liberating. Kelly Clarkson’s Since U Been Gone celebrates the relief and newfound strength that comes after a toxic relationship ends. With its explosive chorus and guitar-driven energy, the song became an anthem for anyone ready to belt out that they’re moving on. It hit the Top 5.

Crying by Roy Orbison

The sound of Roy Orbison’s voice was always best suited to breaking hearts, and there’s no proof of this more than his iconic song of lost love from 1961, ‘Crying’. Orbison finds his old sweetheart after all the time that’s passed, and it’s enough to make him burst into tears, as in ‘Crying’. The song was a hit, reaching the #2 position.

Without You by Harry Nilsson

Harry Nilsson’s 1971 rendition of Without You turned despair into a #1 hit. The verses are soft and sorrowful, then the chorus explodes as Nilsson wails that he can’t go on without love. It remains a definitive ’70s heartbreak anthem that still gives listeners chills.

All By Myself by Eric Carmen

Few songs capture loneliness quite like this 1975 power ballad. All By Myself finds Eric Carmen lamenting being alone after a breakup, set against a sweeping piano and orchestral arrangement. His vocals rise from quiet despair to soaring anguish on the chorus, hitting that empty-apartment feeling perfectly. The song reached #2 in the US and remains a timeless ode to post-breakup solitude.

Jar of Hearts by Christina Perri

Christina Perri’s first single release in 2010 is a haunting warning to a breaker of hearts. ‘Jar of Hearts’ was notable with its dark piano accompaniment, distinct vocals, and angry lyrics. The song represents both sadness and empowerment as it carries a message of not letting the ex cause her more pain. The song was a hit in the US top 20 chart.

Someone You Loved by Lewis Capaldi

Lewis Capaldi’s ‘Someone You Loved’ from the year 2019 is one of those break-up anthems that breaks doves’ hearts. This song is a masterclass exercise in letting go. ‘Someone You Loved’ talks all about adjusting to moving on from a loss. The song remained in the number one position on both sides of the globe. This song has been the tearful motivation of millions of people going through this tough time.

We Belong Together by Mariah Carey

Mariah Carey’s 2005 comeback ballad became a staple of 2000s heartbreak. We Belong Together finds Mariah lamenting a love she lost, listing all the ways life feels wrong without him. Her vocals start restrained and build to emotional, soaring runs by the end. The song dominated the charts for 14 weeks at #1 and remains a go-to track when you’re missing that special someone.

Stay by Rihanna (feat. Mikky Ekko)

Rihanna showed her vulnerable side on this 2013 duet with Mikky Ekko. Stay is a bare-bones piano ballad that pleads for a lover’s presence even when everything hurts. Rihanna’s voice, stripped of her usual production, cracks with raw emotion alongside Ekko’s gentle harmonies. The song resonated worldwide and became a modern staple for those moments when you just want the one you love to stay.

The Tracks of My Tears by Smokey Robinson & the Miracles

This 1965 Motown gem captures the heartbreak behind a brave face. Smokey Robinson croons about smiling to hide the pain – comparing his fake smile to makeup worn since the breakup. His velvety voice and the song’s gentle groove make the sadness palpable. The Tracks of My Tears didn’t hit #1, but it became an enduring soul classic for anyone hiding tears behind a smile.

Neither One of Us (Wants to Be the First to Say Goodbye) by Gladys Knight & the Pips

This 1973 soul ballad captures the agonizing stalemate of a dying relationship. Gladys Knight delivers a powerhouse vocal as both partners are too afraid to end it. The lush arrangement swells with emotion, and the Pips’ harmonies add depth to the heartache. Neither One of Us became one of Gladys Knight’s signature heartbreak songs.

I Will Survive by Gloria Gaynor

Gloria Gaynor’s 1978 disco classic turns heartbreak into triumph. I Will Survive starts as a vulnerable ballad of hurt, then kicks into an upbeat anthem about finding strength and moving on. With its unforgettable chorus and danceable groove, the song hit #1 and became a global symbol of empowerment. Decades later, it still inspires anyone determined to bounce back from a breakup.

The Winner Takes It All by ABBA

‘The Winner Takes It All’, which was a huge hit in 1980 by the Swedish pop sensation ABBA, presents the element of heartbreak in its most articulate form. The song was written after two members of the group split up, and it is clear from Agnetha’s vocal delivery that this song was written from a wounded heart. The song was a chart-topper across Europe, proving that pop stars can be victims of heartbreak as well.

Heartbreak Hotel by Elvis Presley

Elvis Presley’s first #1 hit in 1956, Heartbreak Hotel, paints a stark picture of lonely despair. Elvis’s echoing vocals and the bluesy guitar riffs convey a deep sense of heartache. The song struck a chord and cemented Elvis as a voice for the lovelorn and lonely.

How Can You Mend a Broken Heart by Al Green

Originally a Bee Gees hit, Al Green gave this ballad a soulful makeover in 1972. How Can You Mend a Broken Heart poses its title question with a velvety, melancholic melody. Al Green’s smooth vocals and gentle strings make the pain feel intimate and real, wondering how to heal a broken heart. His version became a soul staple, offering comfort to anyone nursing a broken heart.

When I Was Your Man by Bruno Mars

Bruno Mars stripped down to piano and voice for this heartfelt 2013 ballad. When I Was Your Man finds him reflecting with regret, wishing he had treated his ex better. Bruno’s raw delivery – his voice cracking with pain – struck a chord with listeners. The song hit #1 and remains a modern favorite about longing for the one that got away.

Stay With Me by Sam Smith

Sam Smith’s breakout 2014 hit is a plea from a lonely heart. Stay With Me finds him begging a one-night stand to stay, simply to avoid waking up alone. Smith’s soulful voice, backed by a gospel choir, conveys desperation and vulnerability in every note. The song reached #2 in the US and became a modern classic for anyone grappling with loneliness after love.

Ex-Factor by Lauryn Hill

Lauryn Hill’s 1998 song Ex-Factor has become a ’90s heartbreak anthem. Over a smooth hip-hop soul groove, Hill pours out her frustration and sorrow about a tumultuous relationship. Her voice swings from gentle pleading to full-throated anguish, making every line feel personal. Though never a big chart hit, Ex-Factor is revered by fans as one of Lauryn Hill’s most powerful heartbreak songs.

Somebody That I Used to Know by Gotye (feat. Kimbra)

This quirky 2011 indie-pop track exploded into one of the decade’s biggest breakup hits. Belgian-Australian artist Gotye and New Zealand singer Kimbra trade verses as exes airing their hurt feelings over a xylophone-driven beat. The catchy chorus hook about being treated like a stranger struck a global nerve. The song hit #1 around the world and remains a uniquely catchy take on heartbreak.

I’d Rather Go Blind by Etta James

When it comes to bluesy heartbreak, Etta James’s 1967 song I’d Rather Go Blind is iconic. The title says it all – she’d rather lose her sight than watch her lover with someone else. Etta’s gritty vocals make every line ache with longing. The track didn’t top the charts, but it became a beloved classic often hailed as a pinnacle of soul heartache.

Every Rose Has Its Thorn by Poison

Even hard rockers aren’t immune to heartbreak. In 1988, Poison showed their vulnerable side with Every Rose Has Its Thorn. Lead singer Bret Michaels wrote it after a painful breakup, and the song’s acoustic opening and power-ballad chorus capture the mix of sadness and nostalgia. It became Poison’s first #1 hit and a defining ’80s heartbreak anthem.

It’s Too Late by Carole King

Carole King’s big hit from 1971 is an aural experience of quiet resignation. ‘It’s Too Late’ captures the essence of the end of an association, which has meandered into oblivion with no fanfare or hysteria, merely the acceptance that love has seen its time. The vocals of Carole King on this track stand testament to her talent as her songs always resonate with those love experiences. The song reached No.1.

Total Eclipse of the Heart by Bonnie Tyler

Bonnie Tyler’s 1983 power ballad is full of drama. Total Eclipse of the Heart showcases her raspy voice on top of an epic instrumental. The lyrics describe a lover consumed by love in the dark. The song was a world-wide number one hit and is still a staple of screaming love into a mic.

Everybody Hurts by R.E.M.

Though not about a specific breakup, this 1992 ballad has soothed countless broken hearts. Everybody Hurts reminds us that pain is universal and that you’re not alone in feeling it. A simple, slow melody and Michael Stipe’s earnest vocals give it a lullaby-like comfort. The song became an anthem for anyone going through hard times – a musical hug when you’re feeling down.

Tangled Up in Blue by Bob Dylan

Tangled Up in Blue by Bob Dylan from 1975 is a classic tale of a relationship’s end and how memories of it linger on. The song encompasses all of Bob’s storytelling abilities, where love is lost, its aftereffects, and the consequences. The song did not become a hit single, but it is the poetic expression of the threads of love’s wreckage.

End of the Road by Boyz II Men

In 1992, Boyz II Men delivered a breakup ballad so heartfelt it broke records. End of the Road showcases the quartet’s silky harmonies as they plead for a relationship not to end, even though they know it’s over. The emotion builds to a powerful a cappella bridge. The song spent 13 weeks at #1 on the charts.

Wrecking Ball by Miley Cyrus

Miley Cyrus showed her vulnerable side in 2013 with Wrecking Ball. She sings about the devastation of a love gone wrong – comparing herself to a wrecking ball that destroyed a relationship. The chorus is huge and cathartic, showcasing her powerful vocals. The song swung to #1 worldwide and became an instant heartbreak anthem of the 2010s.

Bleeding Love by Leona Lewis

Leona Lewis’s first single in 2007 was international blockbuster material, focusing on the concept of ‘heartbreak.’ ‘Bleeding Love’ plays on the concept of ‘bleeding’ in describing the emotions that come with ‘bleeding love’ or a dying love. The emotional depth created by Leona’s amazing vocals, paired with heavy pop-R&B production, makes this track an emotional mammoth. It broke into the No.1 position globally.

Hello by Adele

Adele’s soul-stirring 2015 ballad Hello is essentially a phone call to a past love – she apologizes and reflects on everything that went wrong after the breakup. Her powerhouse vocals and the song’s swelling climax gave everyone goosebumps. Hello isn’t just a greeting here – it’s a poignant check-in on a love that still haunts her.

Ain’t No Sunshine by Bill Withers

Bill Withers’ 1971 hit is a masterclass in simple heartbreak. Ain’t No Sunshine runs under three minutes with sparse lyrics, but its message is crystal clear: everything feels dark and empty when she’s gone. Withers’ warm, bluesy voice repeating ‘I know, I know…’ over a gentle groove makes you feel the loneliness. The song reached #3 and endures as a soulful elegy for missing someone.

Purple Rain by Prince

The love song of the century is actually an overflow of sorrowful separation in Purple Rain by Prince in 1984. The combination of rock, gospel, and soul genres makes this song an expression of lost love as the prince wishes his love happy in the purple rain. The song reached its peak position on #2.

Angie by The Rolling Stones

In 1973, The Rolling Stones showed their soft side with Angie, an acoustic ballad of a heartbreaking goodbye. Mick Jagger pours out a bittersweet farewell, accepting that the relationship has run its course. A plaintive piano and string arrangement support Keith Richards’ gentle guitar work. Angie hit #1 and remains one of the band’s most tender, tear-jerking moments.

Say Something by A Great Big World & Christina Aguilera

Other times, a breakup can be ever-so-quiet, which this ballad from 2014 captures perfectly. Say Something is a minimalist Duet of the indie pop duo A Great Big World with Christina Aguilera, which features only a piano accompaniment. The singers plead with someone to give them a sign of how they can cling on to love, which is so emotional that it will make you weep. The song was a Top 5 hit.

Always on My Mind by Willie Nelson

Always on My Mind, an ever-moi song written after regret turned it into a country classic by Willie Nelson in 1982. His soft, aged voice shows regret for not giving as much love as there was, assuring another that it was always on his mind. It remained one of Nelson’s most popular hits despite being written from a regretful experience.