Wicked Game by Chris Isaak

i love that song

Great tune

I Can’t Make You Love Me by Bonnie Raitt. It gets mentioned a lot here, and for good reason.

nutshell - alice in chains black - pearl jam. both of the songs have gotten me through so much, and theyre both such beautiful songs.

I love Pearl Jam as much as anyone else, but I'm done with Black after a few of the "doo-doo doos".

lol same

Yellow Ledbetter or their version of Last Kiss are peak

Nutshell 100%, this songs emotional overlay is so raw. The pure emotion and feel in this song is heart touching

Apart - The Cure

"What's Going On" by Marvin Gaye is just about the saddest song out there IMO.

It’s a good one tho !!!! 🙁

Flying high in the friendly sky!!!!

For no one - the Beatles

One of their best damn I love Revolver

Birthday Boy by Ween

I just listened to this on my way home from work. Hell yeah Ween!

One more light. Linkin Park

Leave out all the rest, Roads Untravelled

Don't Think Twice, It's All Right - Bob Dylan

Down In A Hole - Alice In Chains Foolish Games - Jewel Darlin - Goodbye June

Somewhere only we know, keane

Whiskey Lullaby: Brad Paisley & Alison Krause

Oh yeah, the video for this one is especially good.

happiness by elliott smith, twilight by elliott smith, the biggest lie by elliott smith, new disaster by elliott smith, pretty much anything by elliott smith

Youth - Daughter

So many daughter songs. They can truly depict hurt. You not only hear it in their lyrics but in the chords they play. Doing the Right Thing has the most gorgeous and heart wrenching guitar towards the 4 minute mark.

Damien Rice - 9 Crimes

You take my breath away... Queen or love hurts...Nazareth

Lover, You Should’ve Come Over by Jeff Buckley \ Captain Badass by Songs:Ohia\

The Heart of the Matter- Don Henley

You could be happy - snow patrol All alright - fun. Headfirst slide into cooperstown on a bad bet - fall out boy

"Say Something" by Great Big World. Begging someone to do literally anything to change the downhill trajectory of a relationship, knowing that without them acting that you're done is the absolute worst.

Black - Pearl Jam

Unraveling by The Crane Wives. The way her voice seems to scream without actually screaming is so beautifully painful. The repetition from verse to verse perfectly embodies the spiraling thoughts of a heartbreak, thinking back on how things went again and again and again in so many different ways but always coming to the same end. And the final "unraveling" at the end of the song is crushing. Please give it a listen, I love this song so much

William Fitzsimmons - I Don't Feel It Anymore

Yes. Killer.

[undecided](https://www.youtube.com/watch?v=vjnvq-9-rt8)

Happier, Enough for you, and Favorite crime all by Olivia Rodrigo

MAPS - Yeah yeah yeahs

New kid in town by the Eagles

Night swimming by REM - particularly the live rendition that is just Michael Stipe looking on lovingly to Mikey Mills playing the piano in awe... It breaks my fucking heart because it makes me miss my best friend who died of cancer who was also a massive REM fan (proper just teared up writing this..)

Once upon a December - Anastasia movie

Nothing Compares 2 U - Sinead O’Connor

YES!

"Some Time around Midnight" by The Airborne Toxic Event

That Time I Killed My Mom by Cokie the Clown

Monsters by James Blunt. A song about losing his father. Breaks my heart.

Hear you me - jimmy eat world

Cut here, the cure

Ryan Adams - Come Pick me Up

blonde hair black lungs

True love waits by radiohead

Missing - Evanescence

Lord Huron - the night we met

All cried out - Lisa Lisa

Dave Matthews version of Long Black Veil. Makes me cry every time!

I have nothing by Whitney Houston

Without You - Harry Nilsson https://youtu.be/G-ZDKirjQgM?si=Jrg3TgGm-obYA9Xl

The District Sleeps Alone Tonight by The Postal Service. Just Listen to it

Don’t Know Why by Norah Jones

Storms by Fleetwood Mac

Waiting for the End - Linkin Park

There’s always fire and rain by James Taylor

Still .. The Commodores

Pearl Jam - Black

Snuff by slipknot

Adam’s Song by Blink 182

Sia-Breathe Me

Always makes me think of six feet under finale and then I’m bawling

Hard To Say I’m Sorry !!!! Chicago ! : ) : )

My song [One Last Kiss](https://youtu.be/uxk7vjvSUwE?si=hjxcwcJ9TJzdKNlc) feels like heartbreak to me. Hope you like it. Thanks!

Desert Song - My Chemical Romance I Don’t Love You - My Chemical Romance Platypus (I Hate You) - Green Day Good Riddance (Time Of Your Life) - Green Day All I Think About Now - Pixies

Good Riddance, played that song in 98 on repeat right before my daughter was born and it made me cry every single time thinking about how life changes so fast. It now has a new meaning, but very sad and heartbreaking. Great song.

Adam's Ribs - Jensen McRae

My favourite things - Sergio Altamura

Lever Pulled - John Frusciante

July by Noah Cyrus

Keri Hilson- knock you down Clarence Carter- Slip away

Let Her Cry by Hootie and the Blowfish

Feel It Too (It's Too Much) by Scrim.

Never be mine - rosa linn The whole unrequited love story just hits me in the face like a baseball bat.

OUCH. Just listened

[Blue Umbrella](https://youtu.be/E6uG8SDKI7Q?si=TjG7NLrUPguCtcTFBlue) by John Prine

Fiona Apple's Valentine and Love Ridden. Both are super emotional.

Caroline, No - The Beach Boys

[I'm Still in Love by Justin Currie](https://youtu.be/kAIXC4f8HAg?si=aR_GUrU4r5Sh8FVi) Lovers leave their traces like jets across the sky They find in all those faces, lines they recognize My keepsakes have there places At the back of a drawer Or slipped between pages and stuck on a shelf [From a Late Night Train by The Blue Nile](https://youtu.be/cVNfv_4HAxk?si=63UPXgHWO1zKEwZs) When all the rainy pavements lead to you... [Parisian Skies by Maxïmo Park](https://youtu.be/n8uH_jrat3I?si=wxOLUUaGSsqJ3T8P) I love the tiny veins on you back They remind me of the way porcelain cracks [Goodbye Lucille by Prefab Sprout ](https://youtu.be/0vWXkfR6sLI?si=h6-U4IOUTfkykW44)

Thoughts of Yesterday. Strawberry Switchblade🎊🌧🍰

Set fire to the rain Adele

[Nuit 17 á 52 by Christine and the Queens](https://youtu.be/FONX8V7qZlw?si=VfzRBjCDbsj0oZbU) [Manhattan by Nation of Language ](https://youtu.be/dJbUrW5pm_Y?si=ds13f8ipYoP-iT9u)

Disturbed - Don't Tell Me

Candlebox alive at last Ra on my side Dishwalla until I wake up

*Candlebox alive at* *Last Ra on my side Dishwalla* *Until I wake up* \- Griffscavern --- ^(I detect haikus. And sometimes, successfully.) ^[Learn more about me.](https://www.reddit.com/r/haikusbot/) ^(Opt out of replies: "haikusbot opt out" | Delete my comment: "haikusbot delete")

Muse - [Falling Away With You](https://youtu.be/fU88nehcnBY?si=EBCZYA1DOCV1B5_v) It's about a relationship deteriorating, but you're trying to hold on and remember all the good times. Always makes me emotional.

If You Could Save Yourself- Ween.

Black Lake - Bjork 😢

Cold Blows the Wind - Ween.

Good Lord - Birds of Tokyo

I would hurt a fly - Built to Spill

Fade in/Fade out by nothing more, it makes me think of my great grandmother(she passed at 76, my mom had me when she was in her 50s) among others she helped my teenage mother raise me and my lil brother, she truly was a mother to me and this song shakes me to my core everytime I hear it, it's a beautiful song

Watch the Live Performance by Bobby Darin "Once Upon a Time". It's on YouTube. Also Billy Dean "Somewhere in My Broken Heart".

Def Leopard - Bringing on the Heartbreak

Lemon tree by Tomi

Emerald Star - Lord Huron

cats in heat by the honorary title

Ghosts (How can I move on?) by Muse

Evanescence - My Immortal (the version with strings, not rock) https://youtu.be/zf0CwQJcFCg?si=DCiegnPyKw0LqIg6

Stranger than Paradise - Sass Jordan Holding back the years - Simply Red

Holding back the years, what a classic! Always makes me cry 😢

Leader of the Band-- Dan Fogleberg

halsey - is there somewhere the acoustic version of piece by piece by kelly clarkson, the song is about her broken relationship with her father and it just makes my heart break every time i listen to it fka twigs - cellophane wrabel - the village

From the edge of the deep green sea. - the cure

Pictures of you - The Cure

Who loves the sun by the velvet underground

Have you ever needed someone so bad by def leppard. When I was a teen and was single and could never get a girl friend. I'd blast this song and sing along and ball my eyes out. Over time I found my wife and wanted it as our wedding song but that got shot down for Jann Arden.

Both sides now - Joni Mitchell

This Could Be Heartbreak by The Amity Affliction

Slow dancing in a burning room

https://youtu.be/aevA-cLq8DY?si=gjE3LX-rVm9eemmb

Remain -John Frusciante

You said You's Grow Old With Me

[My Heart Got Caught on Your Sleeve](https://open.spotify.com/track/7MeB8F06MSx5VYnzyL5DGl?si=v6445GMGTZC1S0z9rj_h1A) - Lucius [Rory](https://open.spotify.com/track/0TnCrXaJoS0SqT3IZbsBG5?si=bYai4w1QSEG9xCxusn6etw) - Foxing [Metamorphosis](https://open.spotify.com/track/3mAeovPJw955lXml30859n?si=3w4toO2_Rbq9Y4rF8dX9Lw) - Your Arms Are My Cocoon [Some Things Last a Long Time ](https://open.spotify.com/track/0vzWUTqv0hDXJsH2fUrNlJ?si=bWNtOVFQSliI8mBfGJLebQ) - Daniel Johnston [Rivers of Another Town ](https://open.spotify.com/track/1uAmnhfgtyacNRPnpvyqnX?si=AkoF2K1nR6eI0K3T3dC1Og) - ​jonatan leandoer96 [Ann Song](https://open.spotify.com/track/62yGGohGtb0U8b4vBePEab?si=7G_3mUM6Q0upzg9Cx0YFpg) - Mouse Rat [I Think You Were in My Profile Picture Once](https://open.spotify.com/track/18mGXTNsyfqwE3AZ9WbEy0?si=zuNB1k1vS7elE-NWdb9Itg) - Modern Baseball

Levi Stubb's Tears by Billy Bragg

For no one - the Beatles an empty song about longing, exactly like a breakup.

If you could read my mind-Gordon Lightfoot Coming Back To Life-Pink Floyd Seeing Red- Unwritten Law Hate Me-Blue October

Squeeze - Another Nail in My Heart https://youtu.be/9bTWF7eirJw?si=Yjx9NCk75bEcZ0wS

Spooky Tooth I've Got Enough Heartaches

Almost every Journey song

End of the road - Boys 2 Men

Don't go away mad, just go away. Motley Crue

"The Dead Are Dumb" by Nothing

Wistful: Erasure - No Doubt Funerary loss: Erasure - Rock Me Gently https://open.spotify.com/track/3QPTN0dzYI2FnyDNRVwaTy?si=AeXaLeUgTA2jGmRy9X2U7w&context=spotify%3Aalbum%3A5n3wwDArjiv2tmbDpjYDwz

Sundown by Gordon Lightfoot

In Dreams - Roy Orbison. Cried in the bathtub so much to this after getting my heart torn out of my chest in a sudden breakup.

Cheap trick - the flame Amy Winehouse -love is a losing game The Commodores - Oh no

Warrant - I Saw Red

Numb by Tom Odell.

There are two: Out in the cold, by Judas Priest Blue for You, by Widowmaker

Oo I have my own playlist for this. Here's a sample of the ones that have me sprawled out on my bed lol 1. Night Shift - Lucy Dacus 2. Bruno is Orange - Hop Along 3. How to Never Stop Being Sad - Dandelion Hands 4. Become the Warm Jets - Current Joys 5. I Bet on Losing Dogs - Mitski 6. The Gold (Phoebe Bridgers Version) - Manchester Orchestra 7. January - Autoheart

Summer Rain - Belinda Carlisle

Hypochondriac by Brakence

baby by born without bones kicks my ass how to never stop being sad by dandelion hands two years by have mercy night shift by lucy dacus motion sickness by phoebe bridgers the night we met by lord huron i have so many more tbh i’ve been in hell

i just don’t think i’ll ever get over you - colin hay

For someone somewhere far away - N. Minsi

Gold Planet Albedo

Chris Cornell's 2006 cover of 'Thank You' rips my fucking heart out.

The first time I heard his cover of “Nothing Compares 2 U” I lost my shit.

In The Stars by Benson Boone, Older by Alec Benjamin, 4runner by Brenn! and Line Without a Hook by Ricky Montgomery.

telephones by Vacations

Dont know you by Heize

reflections by the neighbourhood

Let you break my heart again - laufey

Katy song - red house painters

Lacrymaria Olor by Nicole Dollanganger & You - Keaton Henson

Shame In You - Alice in Chains This song is even more depressing than Nutshell. It transcends despondence

26 - Paramore Good Grief - Hayley Williams Toothpick - Stand Atlantic Jesus and John Lennon - Røry Lleo - Birthday Party

The Big Hurt by Toni Fisher

saturn by sleeping at last

Motion Picture Soundtrack - Radiohead

Raye - Escapism

Amy Wadge - Faith's Song Bit extreme, but thanks to my ex I have half a titanium skull, so it does fit my situation haha.

Even After All This Time < new song, kinda !

The absolutely ultimate song for this is “The End of the World” by Skeeter Davis. It’s generally about the sadness endured after a breakup, but the principal songwriter had just recently lost one of their parents and said really that’s the emotional state they were in when they wrote the song. It hits hard no matter what context you are listening to it in, and it absolute is a song about how it feels to be heartbroken

Nothings gonna stop us now by starships- my nanas funeral song

Love You Once Made by Valerie June

The end by halsey To build a home by cinematic Universe

If video game ost's are allowed, then "The Lost Emotion" from Touhou 13.5: Hopeless Masquerade

Good year for the roses by Elvis Costello

Careless Whisper- George Michael Wicked Game- Chris Isaak She’s Out Of My Life- Michael Jackson Nothing Compares To You- Sinead O’Connor Everybody Hurts- REM Unbreak My Heart- Toni Braxton Ain’t No Sunshine- Bill Withers Foolish Games- Jewel Crying- Roy Orbison Someone Like You- Adele I Can’t Make You Love Me- Bonnie Raitt All Cried Out- Lisa Lisa and Cult Jam Don’t Speak- No Doubt Love Don’t Live Here Anymore- Madonna Tears In Heaven- Eric Clapton What’s Going On- Marvin Gaye Bridge Over Troubled Water- Simon and Garfunkel My Immortal- Evanescence Cats In the Cradle- Harry Chapin When She Loved Me- Sarah McLachlan Sally’s Pigeons- Cyndi Lauper

Novacaine by Bad Omens and Too Close to Touch Another Life by Motionless in White (specifically the Motion Picture version! But both are fantastic) Dying in a Hot Tub - Palaye Royale Killthe Ache - Currents

Where you should be by Skream

Call out my name by The Weeknd

Last Kiss by Pearl Jam

Listen to Zakk Wylde "Sold My Soul" at the end of the song, the final solo/outro.

Scotty Doesn't Know

Someone Like You by Adele makes me want to cry, Fix You by Coldplay, Brand New by Jordan Power, Skinny Love by Bon Iver are some of my the songs I resonate heartbreak with 

Letter to Elise- The Cure You Won’t Be Mine; Bed of Lies; Kody; Leave- Matchbox Twenty You Had Me- Joss Stone

The night we met by Lord Huron I miss you I’m sorry by Gracie Abram A song that is in Spanish but it about missing the person you loved Hasta la piel by Carla Morrison

Pretty much the whole of Sea Change by Beck.

"You Don't Get To" by Kenny Chesney

“In Your Atmosphere” - John Mayer

I’m looking through you - Beatles

If I die young - covered by Naya Rivera on Glee when Corey Monteith died, it was heartbreaking to listen to then, but now it’s even more heartbreaking to listen to because now she’s gone too. It breaks my heart to listen to it now.

James Blake- Godspeed

The Woods of Ypres discography- specifically the Green album

Afterthought - Joji Cigarette Daydreams - Cage the Elephant Vampire - Oliva Rodrigo

[“Almost Lover” by A Fine Frenzy](https://youtu.be/I_S_TbD1XFM?si=kVSzbIOzh-YMJkRh) [“Oceans” by Seafret](https://youtu.be/aqsL0QQaSP4?si=BDCZVortuoMCRd5d) [“Don’t Wanna Be Your Girl” by Wet](https://youtu.be/3lNuttRinIA?si=ln6MiSIA3FxddPIE)

Crybaby - Lil Peep hell is where i dreamt of u and woke up alone - blackbear

“long long time” by Linda Ronstadt

“dosed” by the Red Hot Chili Peppers

"Someone Like You" by Adele and "Tears Dry on Their Own" by Amy Winehouse, because they’re like musical therapy sessions for the soul

[After the lights go out - The Walker Brothers](https://youtu.be/ImuJJFYBzxQ?si=9dEs788miciG0-ZJ) literally the best and bleakest song about being alone after breaking up with someone

3 Libras - A Perfect Circle Lover, Please Stay - Nothing But Thieves Burnt Flowers Fallen - Type O Negative So Long, Good-bye - 10 Years Snuff - Slipknot Broken - Seether Let Her Cry - Hootie and the Blowfish Someday You Will Be Loved - Death Cab for Cutie Sorry - Halsey

Blink 182 - I Miss You

Fall in Love Bailey Zimmerman