60 Best Heartbreak Songs of All Time

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Written By Will Fenton

Founder of MidderMusic. From numerous bands to stints working in music shops, read more about me on the 'Here's My Story' page!

Some of the most beautiful songs are inspired by a broken heart. 

And although everyone has a story of their own, songs about heartbreak seem to express that universal feeling perfectly.

Also, these songs can help you get through tough times – they will comfort you and remind you that you’re not alone.

So for today’s article, we made a list of the best heartbreak songs of all time.

From Joy Division to Taylor Swift, you’ll surely find something that fits your mood and situation. 

Table of Contents

1. “All Too Well” by Taylor Swift 

Let’s start with Taylor Swift, a mastermind of heartache songs.

Throughout her career, Taylor has written many relatable songs about a broken heart, inspired by her personal experiences and thoughts about love and relationships.

And her song “All Too Well” got a lot of attention lately, especially because of the short music video starring Sadie Sink.

The song’s lyrics are thought to be based on Taylor’s brief relationship with Jake Gyllenhaal, although she never confirmed it.

Either way, “All Too Well” is very sentimental and powerful, and it’s hands down one of the best heartbreak songs of the decade. 

2. “Someone Like You” by Adele

Another artist that often transforms her personal experiences into music is Adele.

Her incredible vocals, raw emotion, and intricate songwriting skills helped her become a star.

And her signature song “Someone Like You” is arguably one of the best songs about heartbreak.

It’s about finding out that your past love has moved on; and you need to do the same.

3. “Stay” by Rihanna and Mikky Ekko 

Rihanna also recorded many good songs for heartbreak.

In most cases, her music will make you feel confident to move on; but in some songs, she is completely vulnerable. 

“Stay” is the best example – it’s a sentimental piano-driven ballad about different aspects of a romantic relationship. 

It talks about wanting to be reassured that someone loves you but also realizing that things aren’t going as well as you want.

4. “Go Your Own Way” by Fleetwood Mac

If you like Fleetwood Mac, we have a perfect heartbreak song for you – “Go Your Own Way.” 

The song depicts the breakup of the band’s Stevie Nicks and Lindsay Buckingham.

It’s actually Buckingham’s letter to Stevie Nicks.

So, “Go Your Own Way” is yet another Fleetwood Mac song based on the band members’ personal stories and experiences.

5. “Irreplaceable” by Beyoncé 

Besides being one of the best 2000s R&B songs, “Irreplaceable” is also a great song for the broken hearted.

Lyrically, it’s a song about the end of a relationship and Beyoncé saying goodbye to an unfaithful man.

So in a way, the song conveys a message about female empowerment.

One thing is for sure: “Irreplaceable” will remind you that you’re worthy and that you should always stand up for yourself. 

6. “You Oughta Know” by Alanis Morissette 

Another song that will make you feel confident and strong is “You Oughta Know” by Alanis Morissette.

The song is regarded as one of the best girl power songs, and we can see why.

After all, Alanis is known for making motivating, thoughtful music.

And “You Oughta Know” is hands down one of her best hits – it’s honest, powerful, and unapologetic. 

7. “Don’t Speak” by No Doubt 

Released in 1995, “Don’t Speak” was definitely one of the best songs of the year.

In essence, it’s a powerful and emotional portrayal of the pain caused by a failed relationship.

The story is inspired by Gwen Stefani’s personal experiences and relationship with the bassist Tony Kanal.

And one of the messages the song conveys is related to the importance of communication in every relationship.

8. “Apologize” by OneRepublic and Timbaland

Ryan Tedder wrote some of the best songs about broken hearts.

And his 2007 track “Apologize” is definitely the one to remember. 

The song was released on Timbaland’s studio album, but it earned OneRepublic a Grammy nomination.

“Apologize” quickly became a universal hit, and it spent 25 consecutive weeks in the top 10.

9. “Love Will Tear Us Apart” by Joy Division 

Love Will Tear Us Apart” is one of the most popular rock songs about heartbreak.

It’s a good song to listen to after a break up, especially if you feel both melancholic and ready to move on. 

Lyrically, the song is about two people who love each other deeply but eventually grow apart.

It’s a tribute to past loves and loving relationships that simply didn’t survive.

10. “It’s Too Late” by Carole King 

Carole King is a musician that approaches the topic of a breakup in a very mature and sentimental way. 

She released “It’s Too Late” in 1971, and depicted a blameless end of a loving relationship. 

The song also talks about finding the strength to move on.

So if you need a gentle pick-me-up, listening to Carole King might be a good idea. 

11. “Yes” by McAlmont and Butler 

And if you’re looking for a more cheerful song, this one’s for you.

“Yes” by McAlmont and Butler will undoubtedly make you feel better right away.

The lyrics could be interpreted in different ways, but they also fit a situation where you got your heart broken and you’re ready to move on and find someone else. 

Because

Yes I do feel better

Yes I do I feel alright…

12. “Dancing On My Own” by Robyn 

And once you feel better, you’ll be ready to dance.

Although it’s ultimately a broken heart song, “Dancing On My Own” sounds very uplifting and liberating.

The lyrics describe the moment of seeing your ex-boyfriend dance with someone else at a nightclub.

But musically, the song will cheer you up and help you forget about your problems, at least for a moment. 

13. “I Will Survive” by Gloria Gaynor 

“I Will Survive” by Gloria Gaynor is another song that will not only help you move on but also make you dance around your living room.

This song is a timeless classic, and one of the most iconic heartbreak songs.

It’s also a perfect tune to listen to when you need a little reality check.

Because it’s true – it may be hurtful now, but it will pass, and you’ll survive.

14. “I Can’t Make You Love Me” by Bonnie Raitt 

“I Can’t Make You Love Me” is a sad song about heartbreak.

The song tells a story of two people in a relationship but one of them is aware that the love is not reciprocated.

So in essence, it’s about an acknowledgment that you can’t control other people’s feelings.

Bon Iver also made a beautiful cover of the song. 

15. “Somebody That I Used To Know” by Gotye and Kimbra 

“Somebody That I Used To Know” is one of the saddest heartbreak songs. 

Released in 2011, the song conveys raw emotions in a very unique way.

It’s not too dramatic, yet it feels deeply sentimental.

After all, it talks about the complexity of emotions you feel after breaking up with someone.

Gotye was allegedly inspired to write it after not going through a clean break up.

16. “Back To Black” by Amy Winehouse

Amy Winehouse also had her share of heartache songs. 

And “Back To Black” is arguably one of her most memorable tracks. 

It’s emotional, dark, and very powerful.

The song has been interpreted in many ways, and some people claim it’s about Winehouse’s breakup with her then-boyfriend Blake Fielder-Civil.

17. “Un-Break My Heart” by Toni Braxton

Toni Braxton’s “Un-break My Heart” is probably on every list of the best heartbreak songs. 

It’s an R&B classic from 1996, and one of the best-selling singles of all time. 

Lyrically, it’s about wanting someone back – and that’s a common feeling many people deal with after breaking up with someone.

However, if the relationship is over for a good reason, you should let that feeling pass you by.

18. “Thank U, Next” by Ariana Grande

“Thank U, Next” is a heartbreak song that will cheer you up and boost your confidence.

In her 2019 hit,  Ariana Grande emphasizes the importance of self-love.

However, although it’s a catchy, upbeat song, “Thank U, Next”  was written in the aftermath of the death of her ex-boyfriend, Mac Miller.

As a result, Ariana got very emotional during the live performance of “Thank U, Next” at one of her concerts. 

19. “Before He Cheats” by Carrie Underwood

If you’re searching for an angry song about a heartbreak and revenge, this one’s for you.

Carrie Underwood’s “Before He Cheats” is essentially a song about wanting to smash your ex’s car.

Perhaps that’s not the best way to deal with a breakup, but Carrie Underwood’s country hit will at least allow you daydream about it. 

20. “Since U Been Gone” by Kelly Clarkson

You should also add Kelly Clarkon’s “Since U Been Gone” to your heartbreak playlist. 

It’s a song about a breakup, but it’s upbeat and energetic, so it might be the pick-me-up you need right now.

In the song, the protagonist is aware that they fell in love too quickly and they’re glad it’s over. 

After all, not all breakups are sad – most of them are ultimately good for you. 

21. “Skinny Love” by Bon Iver 

“Skinny Love” is a beautiful, heartbreaking song.

It’s very soft and calming, and the lyrics are subtle and poetic. 

The song is taken from Bon Iver’s debut studio album “For Emma Forever Ago.”

The whole album is full of sentimental songs that can help you get through hard times.

22. “Sorry” by Beyoncé

Beyoncé based her whole album “Lemonade” on her personal experiences.

Every song tells its own story, and “Sorry” is related to her husband being unfaithful to her.

Therefore, it’s a great post-breakup song, because it will allow you to process certain thoughts.

Plus, it’s very catchy. 

23. “When Doves Cry” by Prince 

“When Doves Cry” was Prince’s first Billboard Hot 100 No. 1 single.

The song also became his signature song and one of the best heartbreak songs of all time.

According to Per Nilsen (Prince’s biographer), the song was inspired by his relationship with Susan Moonsie, a member of Vanity 6.

24. “I Will Always Love You” by Whitney Houston

Another iconic heartbreak song we can’t skip is “I Will Always Love You.” 

After all, the song is often referred to as one of the greatest love songs of all time.

Whether you agree or not, the song was a huge global success, and it topped the charts in almost all countries.

It was first recorded by Dolly Parton in 1973, but Whitney’s version for the film ‘Bodyguard’ became iconic.

25. “Torn” by Natalie Imbruglia 

Released in 1997, “Torn” by Natalie Imbruglia is such a great throwback song. 

There are many different interpretations of the song’s lyrics though.

But most of them are related to the consequences of a tough breakup.

Nevertheless, the song’s hopeful melody will encourage you to move forward. 

26. “Ex-Factor” by Lauryn Hill

“Ex-Factor” is taken from “The Miseducation of Lauryn Hill”, Lauryn Hill’s iconic album from the 90s.

In the song, Lauryn is referring to her lover and claims that loving him feels like a battle, but it’s also obvious that she loves that person very deeply.

So the song depicts rather complex feelings and the issues of an unhealthy relationship. 

27. “Nothing Compares 2 U” by Sinnead O’Connor

If you’re looking for tender heartbreak music, look no further.

“Nothing Compares 2 U” is slow-paced, gentle, and soulful, and it expresses the emotions of longing and desire. 

The lyrics are written from the perspective of an abandoned lover, so they’re actually quite sad.

By the way, the song was originally composed and written by Prince for his side project, The Family.

28. “Call Out My Name” by The Weeknd 

“Call Out My Name” was released in 2018, and it became an instant hit.

It’s a captivating song about heartbreak and missing someone, and some people claim The Weeknd wrote it about Selena Gomez, who he dated in 2017.

Nevertheless, the song’s lyrics are very straightforward and heart-wrenching. 

29. “Lose You To Love Me” by Selena Gomez 

“Lose You To Love Me” may be even more heart-wrenching.

Selena Gomez released this emotional break up song in 2020.

In the song, she emphasized the importance of self love, acceptance, and personal growth.

And it’s true – knowing that some people might not be good for you is an important step towards getting over someone.

30. “Always On My Mind” by Willie Nelson 

And some people will always be on your mind.

Willie Nelson’s 1982 track “Always On My Mind” is a timeless classic

Writing this song was also his way of apologizing for certain things – and admitting you’re wrong isn’t always easy.

But if you really love someone, being honest is the only option.

31. “Truth Hurts” by Lizzo

On the other hand, truth sometimes hurts.

And Lizzo expressed that in the form of a smooth, catchy tune “Truth Hurts.” 

Although it didn’t chart well right away, the song became a viral hit.

You tried to break my heart

Oh, that breaks my heart…

32. “Say Something” by Great Big World and Christina Aguilera

“Say Something” is a sentimental power ballad about heartbreak.

The song came out in 2014, and it won the artists a Grammy Award for Best Pop Duo/Group Performance.

And Christina Aguilera and Great Big World really work well together – their song is a perfect blend of touching lyrics, powerful vocals, and emotional composition.

33. “Try Sleeping With A Broken Heart” by Alicia Keys 

Alicia Keys released this soulful song on her fourth studio album, “Element of Freedom”, in 2004.

She wrote many songs about a broken heart, but this one really hits differently.

Many agree it’s the best song on the album, and some critics compared it to Prince’s songs. 

That being said, “Try Sleeping With A Broken Heart” definitely deserves a place on this list.

34. “Wrecking Ball” by Miley Cyrus

A good song to listen to if you’re going through a hurtful breakup is “Wrecking Ball.” 

Miley’s catchy power ballad was a huge hit when it came out in 2013.

And everybody assumed it was inspired by her relationship with Liam Hemsworth.

In essence, “Wrecking Ball” is about feeling devastated after a breakup with someone who meant everything to you.

35. “The Scientist” by Coldplay

“The Scientist” has very simple yet sentimental lyrics about heartbreak.

With its familiar melody and a powerful build-up, “The Scientist” is also one of Coldplay’s most beloved songs.

It’s a staple of the band’s live performances since 2002.

Nobody said it was easy

No one ever said it would be this hard…

36. “Lover, You Should’ve Come Over” by Jeff Buckley

“Lover, You Should’ve Come Over” is arguably one of the most beautiful songs for a broken heart.

After all, Jeff Buckley’s aching vocals and approach to music are unmatched. 

In this song, he is contemplating the end of a relationship, and expresses feelings of regret and despair. 

37. “Somebody Else” by The 1975 

“Somebody Else” is hands down one of the best heartbreak rock songs of 2016.

The song tackles the topic of jealousy, as it can be seen in the first verse: ‘So I heard you found somebody else, and at first, I thought it was a lie.’

So the story behind it is tough, but the energy of the song will make you feel hopeful.

38. “Losing You” by Solange

And the same goes for “Losing You” – the song is upbeat and danceable, but it also tells a sad love story.

To be more precise, Solange sings about losing someone, although she gave them everything.

If you’re going through a breakup, you can find solace in “Losing You”, its retro vibes and Solange’s soothing voice.

39. “Rolling in the Deep” by Adele 

Another song by Adele that can help you get over someone is “Rolling In The Deep.”

It’s one of Adele’s signature songs and an absolute heartbreak anthem.

The song won a Grammy Award for Record of the Year in 2011.

And it still gives us chills every time it comes up.

40. “Need You Now” by Lady Antebellum 

Just like “Rolling In The Deep”, Lady Antebellum’s “Need You Now” was released in 2011.

And it remains one of the most popular songs about heartbreak.

“Need You Now” was a huge hit when it came out, and it won four Grammy Awards.

And many artists have covered the song over the years, including Adele.

41. “Broken Strings” by James Morrison ft. Nelly Furtado

“Broken Strings” is another great throwback.

It was released in 2008, on James Morrison’s second studio album.

Nelly Furtado’s vocals fit the song perfectly, and the whole composition as well as the lyrics sound very genuine and authentic.

So it’s no wonder the song became Morrison’s most successful single to date,

 42. “Don’t Think Twice, It’s Alright” by Bob Dylan

If you need a heartbreak song that will lift your spirits up, you can always count on Bob Dylan’s music.

“Don’t Think Twice It’s Alright” has been recorded by many artists, but Dylan’s charm and singing style are unmatched. 

The song feels quite comforting, so it might be exactly what you need at the moment.

Goodbye’s too good a word, babe

So I’ll just say, “Fare thee well”…

43. “Drivers License” by Olivia Rodrigo 

“Drivers License” is an ultimate teenage heartbreak anthem.

The lyrics revolve around being heartbroken and getting over an ex, and they are based on Olivia’s personal experiences.

However, the singer claimed that the person from the song is the least important thing about it.

She simply wanted to transform her experience into a song that will empower other people.

44. “How Can You Mend a Broken Heart?” by Al Green

Al Green’s soulful song from the 70s will provide you with hope and comfort.

Thanks to Al Green’s soothing voice, repetitive guitar, and heartfelt lyrics, this tune truly feels like a remedy.

So, sit back, relax, and let the music take over.

And how can you mend a broken heart?

How can you stop the rain from falling down?

45. “Dreaming With A Broken Heart” by John Mayer 

Another singer you can count on to comfort you is John Mayer.

“Dreaming With A Broken Heart” deals with tough emotions like unrequited love and dreaming of your ex.

But ultimately, the song is encouraging and hopeful, and almost healing. 

46. “Hey, That’s No Way to Say Goodbye” by Leonard Cohen

Leonard Cohen’s heartbreak song is calm, gentle, and poetic.

In the song, he portrayed a simple and mature yet emotional goodbye scene.

And he managed to do it so elegantly – after all, we’re talking about one of the best songwriters of all time.

47. “We Are Never Ever Getting Back Together” by Taylor Swift

Taylor Swift was very clear in her 2012 hit: she is never ever getting back together with her ex.

The song is very catchy and uplifting, so it will definitely motivate you to move on.

It’s taken from Taylor’s album “Red”, which she re-recorded (for “Red (Taylor’s Version)” in 2021. 

48. “Crying” by Roy Orbison

If you’re looking for a song to cry your heart out, this one’s for you.

“Crying” was released in 1962, and it’s regarded as one of the best heartache songs. 

It’s characterized by Roy Orbison’s aching verses, emotional melodies, and pure vintage vibes.

I thought that I was over you

But it’s true, so true

I love you even more than I did before…

49. “Green Light” by Lorde

Lorde released “Green Light” on her 2017 studio album “Melodrama.”

The song is upbeat and danceable, but it’s inspired by a breakup and relatively dark thoughts and feelings. 

In the song, she’s already over it, but she is waiting for her spirit to feel that way.

Until then, she decides to dance, at least according to the video.

50. “River” by Joni Mitchell 

Joni Mitchell’s piano-driven ballad “River” is a beloved Christmas song, but it’s also one of the good break up songs.

Lyrically, it’s about regrets, sorrow, and heartache.

So it’s a sad love song, but Joni’s voice and the melody are so comforting – in other words, this is music for mending a broken heart.

51. “We Belong Together” by Mariah Carey

“We Belong Together” is probably one of the most famous R&B songs about heartbreak on this list. 

It was a huge success when it came out in 2005.

In fact, the song broke chart records in the US, after staying at number one for fourteen nonconsecutive weeks.

Also, Billboard listed it as the song of the decade.

52. “The Winner Takes It All” by ABBA 

ABBA’s music is usually very lively and danceable.

And “The Winner Takes It All” is no different.

However, the song also has a heartbreaking tone to it, and the story behind it is pretty devastating.

It’s about the group’s members Björn and Agnetha – Björn wrote it right after the breakdown of their marriage.

53. “Tears Dry On Their Own” by Amy Winehouse

“Tears Dry On Their Own” will remind you that you can get through anything.

The atmosphere of Amy Winehouse’s signature song is upbeat and hopeful, even though the song depicts her damaging relationship.

In fact, all of the songs on the “Back To Black” album were written during her breakup with actor Blake Fielder-Civil.

54. “Yesterday” by The Beatles 

“Yesterday” is a Beatles classic and one of the most covered songs in history.

It’s a nostalgic ballad about the end of a relationship, written by Paul McCartney.

Throughout the song, the protagonist laments about past times when he was happily in love. 

McCartney reportedly based the lyrics on his dream.

55. “Maggie May” by Rod Stewart 

Rod Stewart’s Maggie May” is one of the most popular 70s songs. 

Stewart wrote it about the first girl he was with when he was 16.

Her name was not Maggie May, but the lyrics are honest, and they depict the emotions of a boy involved in a relationship with an older woman.

56. “Ain’t No Sunshine” by Bill Withers

“Ain’t No Sunshine” is one of the best songs from the 70s.

It’s also regarded as one of the greatest love songs of all time.

Bill Withers left us a substantial musical legacy, and his songs like “Ain’t No Sunshine” will be known to many generations to come.

Ain’t no sunshine when she’s gone

It’s not warm when she’s away…

57. “I’d Rather Go Blind” by Etta James 

And the same goes for Etta James and her timeless classic“I’d Rather Go Blind.” 

Etta James reportedly wrote the song while visiting her friend Ellington in prison.

She wanted to create a song about being blind in love.

Nevertheless, you can interpret the lyrics as you like – along with the soulful melody, they can be very soothing.

58. “Nothing Breaks Like a Heart” by Mark Ronson ft. Miley Cyrus

Nothing breaks like a heart – Mark Ronson and Miley Cyrus are right. 

In 2019, their collaboration song became a universal radio hit.

“Nothing Breaks Like A Heart” was also nominated for Song of the Year at the Brit Awards, and that marked Miley’s first nomination.

59. “New York” by St. Vincent 

“New York” is one of the best indie break up songs.

St. Vincent depicted a long-gone relationship in such a unique and beautiful way.

The song starts off as a gentle piano-driven ballad, and the chorus transforms into something more powerful.

New York isn’t New York without you, love…

60. “When I Was Your Man” by Bruno Mars

Bruno Mars often sings about love and relationships, and from time to time he records a heartbreaking ballad.

In “When I Was Your Man”, he describes the regret he felt after letting his lover get away.

However, he hopes her new lover will give her love and devotion he failed to provide..

Best Heartbreak Songs – Final Thoughts 

If you’re here because you’re heartbroken, we hope our playlist helped you feel a little better.

Listening to relatable music can make you feel understood and help you process your emotions.

At the end of the day, some of the most beautiful love songs were written by someone with a broken heart.

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