1“Complex (Demo),” by Katie Gregson-MacLeod
Let’s begin with the obvious: the song that infiltrated every corner of TikTok for months, inspiring other songwriters on the app to duet the original chorus with musings of their own.
Most Heartbreaking Lyric: I need him like watеr / He lives on a landslide / I cry in his bathroom / Hе turns off the big light
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2“Better Version,” by Fletcher
The most heartbreaking track off Fletcher’s debut album, Girl of My Dreams, “Better Version” explores the most painful all-too-relatable aspect of a breakup: watching someone else get the “better version” of the person you lost.
Most Heartbreaking Lyric: It’s always the next person / That gets the better version / ’Cause baby, I loved you at your worst / And I fixed your heart, but mine still hurts / And now some other person / Is gonna get the better version of you
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3“And I’d Go a Thousand Miles,” by Montell Fish
Montell Fish’s latest album, Jamie, is full of sad tracks from start to finish, no skips. The entire album is a processing of grief, and when you realize that, this track is even more devastating.
Most Heartbreaking Lyric: And I still can’t find you / Where did you go? / And my feet so tired / But this love I hold
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4“Let the Grass Grow,” by Ruel
This one is sad, but not breakup sad. It’s more of a “the planet is burning and I’m feeling hopeless” sad.
Most Heartbreaking Lyric: There’s nothing to fill this void / Start turning into sorrows / So I lay here soaking the sand in my bed / What a day to regret
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5“In the Kitchen,” by Reneé Rapp
Broadway alum and breakout star of HBO Max’s The Sex Lives of College Girls Reneé Rapp dropped two new singles this year, one of them being this breakup ballad that hurts so good.
Most Heartbreaking Lyric: So I’ll dance with your ghost in the living room / And I’ll play the piano alone / But I’m too scared to delete all our videos / ’Cause it’s real once everyone knows
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6“Matilda,” by Harry Styles
Play it louder for the sad kids in the back! The most somber track off Harry Styles’s latest album Harry’s House, “Matilda” was inspired by both the classic novel Matilda and a person Harry knew who struggled with a less-than-loving family.
Most Heartbreaking Lyric: Nothing about the way that you were treated ever seemed especially alarming till now / So you tie up your hair and you smile like it’s no big deal
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7“Something in the Orange,” by Zach Bryan
This breakup track brought Zach Bryan from #9 to #1 on Billboard’s Emerging Artists chart and, like any great tearjerker, has grown legs on TikTok.
Most Heartbreaking Lyric: There’s orange dancin’ in your eyes from bulb light / Your voice only trembles when you try to speak / Take me back to us dancin’, this wood used to creak
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8“The 30th,” by Billie Eilish
If you’re looking for a sad song that will take you on a journey through a specific story, look no further. Billie’s newest song is about coping with a friend’s terrible car accident.
Most Heartbreaking Lyric: And I know you don’t remember calling me / But I told you even then you looked so pretty / In a hospital bed / I remember you said you were scared / And so was I
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9“Nostalgia,” by Suki Waterhouse
This is for the one you still can’t get over.
Most Heartbreaking Lyric: I talk about the past like I talk about you / I leave out every little thing that I don’t like remembering / I miss you more than I say I do
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10“Glimpse of Us,” by Joji
Guarantee you’ve heard at least a few bars of this on TikTok, but take a moment to listen to the whole song through and you’ll be a puddle on the floor.
Most Heartbreaking Lyric: Tell me he savors your glory / Does he laugh the way I did? / Is this a part of your story? / One that I had never lived
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11“Family Line,” by Conan Gray
Conan Gray sure fed his fans an entire album’s worth of sad songs, but “Family Line” is the most heart-wrenching, and it’s deeply personal to the artist on top of being devastating.
Most Heartbreaking Lyric: Oh, all that I did to try to undo it / All of my pain and all your excuses / I was a kid but I wasn’t clueless / (Someone who loves you wouldn’t do this)
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12“Anybody Else,” by Faouzia
Faouzia’s beautiful song about love gone wrong really showcases her voice, which you can appreciate through your own sympathetic tears.
Most Heartbreaking Lyric: Can we go back to a time when / You were just a stranger and my heart was strong? / It’s a cruel love, never-ending / Looking here for something, but it’s gone, gone, gone
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13“It’ll Be Okay,” by Shawn Mendes
Released following his split from Camila Cabello (nope, still not over it), this weepy song from Shawn Mendes hits HARD.
Most Heartbreaking Lyric: Oh, the future we dreamed of is fading to black / Oh, there’s nothing more painful / Nothing more painful
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14“Doppelgänger,” by Joshua Bassett
There is literally no denying that this breakup ballad from Joshua Bassett is about Olivia Rodrigo (especially after you watch the music video).
Most Heartbreaking Lyric: I know we’re getting older / We’re moving on and over / But everywhere I go, I see your face
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15“Fingers Crossed,” by Lauren Spencer-Smith
This breakup anthem from American Idol alum Lauren Spencer-Smith went mega-viral on TikTok for a reason: It’s relatable AF.
Most Heartbreaking Lyric: Making plans to travel round the world / Said we’d always put each other first / Old love songs we used to play to / Funny, now I hate you
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16“Hate Me if It Helps,” by Alexander 23
Cowritten by Olivia Rodrigo, Alexander 23’s latest single reflects on his own experiences with heartbreak, which is probs why it cuts so deep.
Most Heartbreaking Lyric: Do you wonder if I’m with someone new now? / If her clothes are in the drawer you used to take up in my room? / Yeah, I bet you think I never think about / You anymore, and god, I wish that that were true
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17“Softly,” by Arlo Parks
Anyone who’s ever dealt with the confusion and desperation of a dying relationship will be able to relate to this devastating new single from Arlo Parks.
Most Heartbreaking Lyric: If I upset you, could you maybe say so? / Has something changed, have I just missed the memo? / Tell me what I don’t know
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18“Invincible,” by Omar Apollo feat. Daniel Caesar
While the music video for Omar Apollo’s “Invincible” is delightfully trippy, the lyrics will definitely break your damn heart.
Most Heartbreaking Lyric: I had to call you back to tell you that / You could have spared my feelings / I’m not invincible
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19“When You Look at Me,” by Sara Kays
Is there anything more devastating than realizing the person you love no longer feels the same way? Probably not, tbh (but fret not—Sara Kays feels your pain).
Most Heartbreaking Lyric: You keep saying you don’t remember / Hate that I have to tell you / How you told me I remind you of the moon / And you’d hold me and that now you never do
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20“Shadow of Mine,” by Alec Benjamin
Alec Benjamin’s latest is all about the challenges that come with learning to love yourself, including those dark parts you’d rather ditch for good.
Most Heartbreaking Lyric: It goes everywhere I go / It won’t ever let me go / This shadow, this shadow of mine / We grapple, we battle, but we / Are shackled for eternity
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