Top 20 Most Heartbreaking Pop Songs

MsMojo

Dive into a soul-stirring journey through some of the most heart-wrenching pop songs ever created. From tales of lost love and grief to moments of deep regret and loneliness, these tracks will hit you right in the feels. Featuring emotional anthems by Adele, Beyoncé, Eric Clapton, and more, this list is for anyone who’s ever felt their heart break through the power of music.

Transcript

00:00I don't need you, I find a strength I've never known.

00:05Welcome to Ms. Mojo.

00:07And today, we're counting down our picks

00:09for the pop songs that hit where it hurts.

00:12Lost love, grief, regret, loneliness, and more.

00:15And look, we love a good cry to my immortal

00:17as much as the next person, but since it's not pop,

00:20it will not be on our list today.

00:22Are you looking down upon me?

00:25Are you proud of who I am?

00:30Number 20, Incomplete, Backstreet Boys.

00:33If you've ever watched a relationship

00:35slowly slip through your fingers,

00:37you'll get exactly where the Backstreet Boys are coming from.

00:40Empty spaces fill me up with holes.

00:46The group previously explored the theme of deep isolation

00:49in Show Me the Meaning of Being Lonely,

00:51but here, they lean into the depleted reserves

00:54of trying to fix what's irrevocably broken.

00:56I tried to go out like I never knew you.

01:03There's no big bust up,

01:04but more just the sobering realization

01:06that you're desperately trying to bridge a gap

01:08that only keeps widening.

01:10With a soaring chorus and vulnerable delivery,

01:13it captures that agonizing, quiet moment

01:15when you finally admit that love alone

01:17just isn't enough to sustain

01:19what has already drifted too far apart.

01:22All I'm going to be is incomplete...

01:29Number 19, Sandcastles, Beyonce.

01:33Listening to Sandcastles almost feels like

01:35we're intruding on a private, searingly honest confession.

01:38We built sandcastles that washed away...

01:47Featured on Beyonce's monumental Lemonade album,

01:50this piano-driven piece explores the fragile nature of trust

01:53following a devastating betrayal.

01:56Instead of focusing on the rage,

01:57she hones in on the sheer exhaustion

01:59of trying to rebuild a foundation that has been washed away.

02:06Beyonce lets her raw, unpolished emotions

02:09drive her voice in a way that will resonate with anyone

02:11who has felt like they're helplessly watching

02:13their relationship crumble.

02:15It's a gut-wrenching look at the price of forgiveness

02:17and the terrifying uncertainty that lingers long

02:20after the initial storm has finally passed.

02:31Number 18, Yesterday, The Beatles.

02:34Few songs have become so universally sad

02:36with so little effort.

02:38Yesterday, all my troubles seem so far away.

02:45Yesterday is so beautifully understated,

02:48a man looking back on a life that no longer feels the same,

02:51rather than relying on melodrama.

02:53The song builds its power through pure regret,

02:56loneliness, and a deep aching sense of longing

02:59that sits right in your chest.

03:00That restraint makes the pain even sharper.

03:03Why she had to go?

03:07I don't know she wouldn't say.

03:11The Beatles helped turn a simple reflection

03:13into one of pop music's most enduring emotional gut punches.

03:17It strikes a universal chord because everyone understands

03:20the feeling of wishing you could go back.

03:22This song remains a timeless, haunting,

03:24and incredibly relatable masterpiece of sorrow.

03:27Oh, I believe in yesterday.

03:32Number 17, Till It Happens To You, Lady Gaga.

03:36Anyone who has struggled to be understood

03:38while carrying trauma will recognize

03:40the isolating reality depicted in this ballad.

03:43Till it happens to you,

03:45you won't know it won't be real.

03:50How can you know?

03:52Written for the documentary, The Hunting Ground,

03:54it addresses the painful aftermath of sexual assault.

03:58Gaga's powerhouse vocals convey a level of visceral,

04:01unfiltered agony that is truly difficult to shake.

04:05Tell me, hold your hand up,

04:08hold your hand up,

04:10and be strong.

04:11It's an incredibly brave piece of songwriting

04:14that demands empathy,

04:16forcing us to confront a reality

04:17that many choose to ignore.

04:19By giving a voice to the voiceless,

04:21she created a song that doesn't just break your heart.

04:23It challenges your entire perspective on pain,

04:26survival,

04:27and the absolute necessity of being truly heard.

04:30I don't want to hear anything from you,

04:34from you, from you.

04:36You don't know.

04:43There is a specific, hollow helplessness

04:46that comes with watching a loved one lose their way,

04:49a feeling that The Fray captured perfectly in this track.

04:52Where did I go wrong?

04:55Lost,

04:57somewhere alone in the bed I left.

05:00Inspired by Isaac Slade's experience

05:02working at a youth retreat,

05:04the lyrics explore the crushing weight

05:06of trying and failing to help a loved one

05:08who is slipping away.

05:09It's a song about the harsh truth

05:11that some crises are too deep

05:13for even the most devoted friends to resolve.

05:15He'll say he's just not the same,

05:19and you'll begin to wonder why you came.

05:23The desperate, soaring melody mirrors the internal struggle

05:26as he grapples with the endless what-ifs.

05:29It's a haunting anthem for anyone

05:30who has tried sharing in the difficult

05:32and heavy burden of someone else's crisis.

05:35But I stayed up with you all night

05:39And I know how to save a life

05:44Number 15.

05:46Who knew?

05:47Pink.

05:47Pink has always been real about life's hardest moments,

05:50but Who Knew is definitely her most harrowing song.

05:53If someone said three years from now

05:57You'd be long gone

06:00It's all about losing a friend,

06:02and she doesn't want to hold back

06:03on how messy, painful, and confusing

06:05that kind of sudden loss actually feels.

06:08Much like her exploration of fractured family dynamics

06:10and family portrait,

06:12she refuses to sugarcoat the pain

06:13of being the one left behind.

06:15Who Knew captures that exact moment of shock

06:18when you realize someone you made future plans with

06:20is no longer around to see them through.

06:23That last kiss

06:25I'll cherish

06:26Until we meet again

06:29It's a brutal reminder of how fragile our connections truly are

06:34and how much we leave unsaid.

06:36Who knew?

06:38I'll let you

06:39I'll miss you

06:40I'll let you

06:42Who knew?

06:44Number 14.

06:46Say Something

06:47A Great Big World

06:48and Christina Aguilera

06:49Have you ever reached that point in a relationship

06:52where the energy just runs out

06:54and you realize you're holding onto a ghost?

06:56And I

06:59Am feeling so small

07:02This song is basically the soul-crushing equivalent of waving a white flag.

07:07It perfectly captures those final desperate moments of a relationship gasping for air.

07:12The way they sing together feels so intimate,

07:14almost like you're eavesdropping on a private and deeply taxing breakup argument.

07:18You're the one that I love

07:23And I'm saying goodbye

07:25It gives off that quiet, hollowed out feeling you get

07:28when you finally accept that you've done all you can.

07:31For anyone who's waited to reignite a spark that's long gone,

07:34it's a brutal, beautiful, and resigned surrender.

07:37Say something

07:38I'm giving up on you

07:41Number 13.

07:43Monsters

07:44James Blunt

07:45Many of us have dealt with that terrifying moment when suddenly

07:48you realize you're the one who has to be strong for your hero.

07:52Tell you I love you once more

07:56The time has gone

07:57Blunt wrote this for his father while he was critically ill.

08:01And it's such a fragile, honest message.

08:04The music is really stripped back,

08:06which just puts his vulnerable, almost cracking voice front and center,

08:10making every lyric feel so heavy.

08:12And while you're sleeping, I'll try to make you proud

08:16He turns a deeply personal family moment into something we can all understand.

08:21That fear of losing someone before you're ready to let go.

08:24It's a powerful reminder to tell the people we love how much they mean to us while we still can.

08:29Don't be afraid

08:32It's my turn

08:34To chase the monsters away

08:36Number 12.

08:38Supermarket flowers

08:39Ed Sheeran

08:41The most piercing parts of saying goodbye are often the quiet, everyday moments that suddenly feel empty.

08:46Hallelujah

08:49You were an angel in the shape of my mom

08:53Ed Sheeran captured this perfectly in his tribute to his late grandmother,

08:57written from his mother's perspective.

08:59By avoiding abstract statements about sorrow to focus on tactile, painful details,

09:05like clearing out a bedroom or spotting wilting flowers,

09:07he captures a side of loss that feels almost too real,

09:11and hit way harder than many poems ever could.

09:21It's a gentle, deeply sad goodbye that serves as a quiet, beautiful reminder of the love that stays with us

09:27long after someone we cherish is finally gone from this world.

09:31When God took you back, he said hallelujah, you're home

09:37Number 11.

09:39Liability

09:40Lord

09:40This song, from Lorde's second studio album, Melodrama, never fails to grip us.

09:46Baby really hurt me, crying in the taxi

09:49He don't wanna know me, says he made the big mistake of dancing in my storm

09:54Per the singer's own admission, liability is about how she thought she was too much.

09:59It's safe to say that most of us have been there at one point or another.

10:02They say, you're a little much for me

10:07You're a liability

10:11You're a little much for me

10:14And the track, which she co-wrote with Jack Antonoff, really encapsulates that harrowing sensation.

10:20Lorde sings about being nothing more than a toy for others, and feeling that nobody will be able to love

10:25all of her.

10:26The truth is, I am a toy that people enjoy, till all of the tricks don't work anymore

10:35And then they are born of me

10:39Her powerful delivery drives the number's heart-wrenching message home, with the piano tones making the whole thing all the

10:45more poignant.

10:46We hope Lorde never stops taking up space, because she's anything but a liability

10:51You're all gonna watch me disappear into the sun

11:02Number 10. Someone Like You

11:04Adele

11:05Breakups are never easy, but Someone Like You is the perfect song for when you need to let yourself feel

11:11the pain that comes after one

11:20Inspired by heartbreak in her own life, Adele vividly bares her soul, addressing what it's like when the one you

11:26love has moved on

11:27It's an affecting look at the fear and hurt that follow, but there's no anger

11:32Never mind, I'll find someone like you

11:38Instead, you can sense the sadness in her voice

11:41Which is complemented perfectly by the simple yet robust melody

11:44And the singer is constantly finding new ways to touch our hearts

11:48Sometimes it lasts in love, but sometimes it hurts in space

11:55Just look at My Little Love, the moving song from her 30 album

12:00I'm so far gone, and you're the only one who can save me

12:06Adele never stops bringing the emotion, and it always hurts in the best way

12:10Number 9. Unbreak My Heart

12:13Toni Braxton

12:14This ballad tells the tragic tale of a woman who's had her heart shattered

12:27She's suffering and wants things to go back to the way they were before her world was turned upside down

12:32The song could be describing a difficult split between two people

12:35But it could also be about the grief one feels after a significant other's passing

12:48Indeed, we see the latter scenario play out in the music video

12:52Adding a layer of sadness to every lyric

12:55Braxton's delivery is so impassioned that we experience the agony behind every word on a deeper level than we thought

13:01possible

13:11It's an unbelievably touching number

13:13And we don't think we'll ever be able to un-cry the tears that it made us shed

13:17Number 8. Because of You

13:20Kelly Clarkson

13:21Kelly Clarkson was just 16 years old when she first penned this grim song

13:25I will not make the same mistakes that you did

13:31It's thought to allude to her difficult home life as a child

13:34As her parents split up and her father left

13:37The evocative lyrics chronicle the lasting effect of such experiences

13:40Describing a lack of trust and a fear of taking risks

13:43Because of You

13:45I never stayed too far from the sidewalk

13:49They also powerfully address a desire to do things differently

13:53Clarkson's strong vocals blend flawlessly with David Hodges and Ben Moody's rousing production

13:59Resulting in a song that'll have you sobbing as you belt along

14:02The singer later tackled similar themes with the emotional but optimistic piece by piece

14:27We recommend playing both songs back to back if you really want to feel your feelings

14:41Number 7. Every Time

14:44Britney Spears

14:45Britney Spears has treated us to a slew of iconic songs

14:48And Every Time is one of the most noteworthy in her discography

14:51The track doesn't rely on over-the-top gimmicks to grab listeners' attention

15:03In fact, it's quite the opposite

15:13It resonates because it strips everything back

15:16Allowing Spears' vulnerability and voice to shine through

15:19In doing so, the spotlight remains fixed on the story of a remorseful young woman

15:24Whose heart has been irreparably broken

15:35As if that wasn't profound enough on its own

15:37The music video takes things up a notch with its morbid but ultimately hopeful imagery

15:41Every time I see you in my dreams

15:46I see your face

15:48You're haunting me

15:50It goes without saying, but every time we try to play this song without losing our composure

15:54We fail

15:55Number 6. Praying

15:57Kesha

15:58Kesha showed everyone just how talented she is with this striking ballad

16:13There's a triumph in the song

16:14As she sings about her newfound strength

16:16But it's also evident that she had to face an unimaginable amount of pain

16:21And you can't help but feel devastated

16:29Widely believed to be aimed at Dr. Luke

16:31Whom Kesha has sued for assault and severe mistreatment

16:34The track is both heartbreaking and empowering

16:36I hope you're somewhere praying

16:42It's a declaration of freedom

16:44An acknowledgement of suffering

16:46And contains the hope that even the worst people can change

16:49Kesha's sincere performance is absolutely stunning

16:52And her ability to speak her truth is awe-inspiring

16:55Praying won't leave anyone indifferent

16:57And will never stop playing it

17:00I hope you find your peace

17:04Falling on your knees

17:08Praying

17:10Number 5. Before You Go

17:12Lewis Capaldi

17:13Lewis Capaldi released Before You Go in 2019

17:16Blowing us all away with his sheer artistry

17:19I feel by the wayside

17:21Like everyone else

17:23I hate you, I hate you, I hate you

17:26But I was just kidding myself

17:27The song is a profound exploration of what happens after someone you love takes their own life

17:33There are no words to address such a tragedy

17:36But he somehow finds them

17:37When you heard under the surface

17:41Like troubled water running cold

17:47Accompanied by smooth guitar sounds

17:49The artist goes through a range of complex emotions

17:52Wondering if he could have somehow altered the course of events

17:55And the way his raspy voice soars during the chorus is nothing short of bone-chilling

18:01Was there something I could have said to make it all stop hurting?

18:07Through this mournful track

18:08Capaldi sheds light on a topic that's often considered taboo

18:12In an honest, nuanced, and thoughtful way

18:15Needless to say

18:16It's a heavy and potent number

18:18But one that's definitely worth hearing

18:26Number four

18:27Hurt

18:28Christina Aguilera

18:29Grief and regret are two incredibly loaded topics to tackle

18:33Even individually

18:34Seems like it was yesterday

18:37When I saw you fade

18:39Christina Aguilera's Hurt does the unthinkable

18:42And blends both of them together

18:44The number sees Aguilera singing from the perspective of a grieving woman

18:47I would hold you in my arms

18:51I would take the pain away

18:54The lyrics paint a gloomy picture

18:56As she apologizes to her late loved one for how things unfolded

19:00And explains how much she misses them

19:02That heavy message

19:03Combined with the singer's commanding yet solemn vocal

19:06And the breathtaking instrumentals

19:08Make for an extra gut-wrenching listen

19:10And I've hurt myself

19:14By hiding you

19:17Co-writer Linda Perry

19:19Drew from her own experience

19:20Losing her father

19:21To help create this song

19:23And the emotion is immediately discernible

19:25It feels personal because it is

19:27And that's precisely why it's so impactful

19:30And I've hurt myself

19:36Number three

19:37Anyone

19:38Demi Lovato

19:39Demi Lovato has never shied away

19:41From discussing their mental health

19:43I tried to talk to my piano

19:46I tried to talk to my guitar

19:50Anyone is no exception

19:52Providing an intimate glimpse into their state of mind

19:54Prior to their near-fatal 2018 overdose

19:57Lyrically, the song addresses feelings of hopelessness and sorrow

20:11There's an ache and agony that runs through the haunting melody

20:14And emotive vocals

20:15Describing what it's like when you're tired of screaming into the void

20:26The blunt ballad is sure to give any listener goosebumps

20:29Lovato even restarted their performance of the song at the 2020 Grammys

20:33After getting emotional

20:34I tried to talk to my piano

20:46We'd be lying if we said we weren't choking up too

20:48There's no doubt that anyone has helped many people feel seen

20:52And it'll forever remain one of the singer's most chilling releases

20:55Anyone

20:57Anyone

20:58Please send me

20:59Anyone

21:00Lord, is there anyone

21:05I need someone

21:07Number two

21:10Ronan

21:11Taylor Swift

21:12Ronan was an amazing little boy

21:14Who unfortunately died from cancer

21:16Shortly before his fourth birthday

21:18I remember your bare feet

21:21Down the hallway

21:22I remember your little laugh

21:26Taylor Swift discovered his story through his mom Maya Thompson's blog

21:30Which ultimately led to this heartbreaking song

21:33Originally released in 2012

21:35And re-recorded nearly a decade later for Swift's Red, Taylor's version album

21:39Ronan is as poignant today as ever

21:42Come on baby with me

21:44We're gonna fly away

21:46From here

21:48The lyrics capture the grief that comes with losing a child in a soul-stirring way

21:53And beautifully honor Ronan and his mother

21:55There's remembrance, pain, and above all, an infinite amount of love

22:00What if the miracle was even getting one moment with you

22:08The song's raw emotion is so palpable

22:10That it's impossible to get through it without breaking down and bawling

22:14You're definitely going to want to grab a tissue box before listening to this one

22:18Before we unveil our top pick

22:30Here are a few honorable mentions

22:32There You'll Be

22:33Faith Hill

22:34Hill sings about finding comfort in memories of someone who was gone but never forgotten

22:39In my heart there'll always be a place for you

22:43For all my life

22:46Nothing compares to you

22:48Sinead O'Connor

22:49A reflection of the soul-crushing void left behind when an irreplaceable partner walks away forever

22:54Nothing compares

23:00Nothing compares

23:03Falling

23:03Harry Styles

23:05A very reflective breakup ballad

23:07What if I'm someone you wanna talk about

23:11I'm falling again

23:14Didn't We Almost Have It All

23:16Whitney Houston

23:17A heart-wrenching realization that a dream romance was ultimately doomed from the start

23:22Didn't We Almost Have It All

23:28Stay

23:29Rihanna featuring Mickey Echo

23:31Desperate plea to avoid the inevitable end of a volatile, consuming love

23:36Funny you're the broken one

23:38But I'm the only one who needed saving

23:44Cause when you never see the light

23:47It's hard to know which one of us is caving

23:57Before we continue, check out this single from Current, EDM Transformed

24:02Check out the full track and album below

24:131. Tears in Heaven, Eric Clapton

24:16Tears in Heaven is built on a soft, melodic, and easy-to-love structure that fits right into

24:21the pop tradition

24:22Even if it carries the heavy emotional weight of folk and adult contemporary music

24:27It even earned Clapton a Best Male Pop Vocal Performance at the Grammys back in 1993

24:43More importantly, it reached an enormous audience through its unforgettable melody

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