45 crushing songs for sad boys and girls

What do you do if you feel a bit down? Do you address your problems, get to the root of them and work to solve them? Or do you, at least for a while, listen to something that gets you in your feelings? While the exact songs and artists that make you feel things is deeply personal, we’ve put together a list of some of the best songs by sad boys and sad girls. 

There’s no real criteria: the songs span genres, from indie to emo, RnB to rock. What most of them share, however, despite the occasional acoustic guitar, is an indescribable feeling. They deal with heartbreak, loss, grief and complex feelings around growing up and the futility of life. They’re all perfectly suited to putting in your earphones, leaning your head against the passenger window, and thinking a lot about everything. Enjoy! Or don’t, if the intention is to hurt your own feelings.

Sad Girls

1. ‘Sullen Girl’ – Fiona Apple

Released in 1996, the dark, sombre ‘Sullen Girl’ deals with the aftermath of Fiona Apple’s assault. On her recent album, ‘Fetch the Boltcutters’, Apple proved she’s still the gold standard for experimental songs about comple feelings.

Saddest lyric:And there’s too much going on/but it’s calm under the waves/in the blue of my oblivion

2. ‘Funeral’ – Phoebe Bridgers

On ‘Funeral’, Bridgers somehow articulates her feelings of sadness and grief at the loss of a friend with absolute precision.

Saddest lyric: Jesus Christ, I’m so blue all the time/and that’s just how I feel/always have and I always will

3. ‘Happiness is a butterfly’ – Lana Del Rey

Del Rey’s latest release, ‘Norman Fucking Rockwell’, was full of dreamy, sad songs, but simple piano ballad ‘Happiness is a butterfly’ wins out.

Saddest lyric:If he’s a serial killer, then what’s the worst that could happen to a girl who’s already hurt? I’m already hurt.”

4. ‘Nobody’ – Mitski

Maybe it’s because we’ve all been lonelier than ever lately, but Mitski’s ‘Nobody’ hits hard, perfectly encapsulating the longing of being alone.

Saddest lyric: “I’ve been big and small/and big and small/and big and small again/and still nobody wants me”

5. ‘Back to Black’ – Amy Winehouse

Even sadder in the wake of Winehouse’s death, soul song ‘Back to Black’, on which she mourns a breakup while referencing her heroin addiction, is beautiful.

Saddest lyric:We only said goodbye with words/I died a hundred times/you go back to her/and I go back to/black

6. ‘My Life’ – Best Coast

Despite being more known for their lazy stoner girl bops, with ‘My Life’, Best Coast hit the nail on the head for a very particular desire to change and feel better.

Saddest lyric: “My mom was right/I don’t wanna die, I want to live my life 

7. ‘Nineteen’ – Hayley Williams (Tegan and Sara cover)

While ‘Nineteen’ is pretty emotional in its own right, Hayley Williams’ voice brings its own weight to this Tegan and Sara cover.

Saddest lyric: Flew home, back to where we met/stayed inside, I was so upset/cooked up a plan so good except I was all alone

8. ‘Praying’ – Kesha

Her first release after her traumatic battle with Dr Luke and Sony, Kesha’s ‘Praying’ is a powerful song about recovery and forgiveness.

Saddest lyric: You brought the flames and you put me through hell/I had to learn how to fight for myself

9. ‘Misguided Ghosts’ – Paramore

Queen of the sad girls, Hayley Williams deserves a whole list to herself, but ‘Misguided Ghosts’ is a perfectly sorrowful Paramore song.

Saddest lyric: And now I’m told that this is life/that pain is just a simple compromise/so we can get what we want out of it

10. ‘I’m With You’ – Avril Lavigne

Sometimes you just need to walk around in the rain with your earphones in pretending you’re 12 again, and sometimes Avril is the only way to reach that emotional space.

Saddest lyric: Nothing’s going right/and everything’s a mess/and no one likes to be alone

11. ‘Wake Up Exhausted’ – Tegan and Sara

Sad girl sister duo Tegan and Sara have a lot of deep songs in their back catalogue, but ‘Wake Up Exhausted’ captures a particularly relatable, raw desperation.

Saddest lyric: I hated this city before you came here/so let go and move on/we’re strangers, we’re not friends/I hate this and I hate them

12. ‘Hide and Seek’ – Imogen Heap

The O.C. soundtrack is full of sad songs, and while its use of Imogen Heap’s ‘Hide and Seek’ was pretty funny, the song itself still hits the spot.

Saddest lyric: “Speak no feeling, no, I don’t believe you/you don’t care a bit, you don’t care a bit

13. ‘Running Up That Hill’ – Kate Bush

Ostensibly about Bush’s longing to swap places with a man and find out how easy it might be, ‘Running Up That Hill’ is open to interpretation and much, much contemplation.

Saddest lyric: “If I only could/I’d make a deal with God/and I’d get him to swap our places/I’d be running up that road/be running up that hill/with no problems

14. ‘Dancing On My Own’ – Robyn

Robyn’s ‘Dancing On My Own’ will forever be the perfect song for the inexplicable onset of loneliness that can engulf you in the middle of a crowd, even on a dancefloor.

Saddest lyric: “So far away, but still so near/(The lights go on, the music dies)/but you don’t see me standing here/(I just came) to say goodbye

15. ‘Stonemilker’ – Björk

Björk’s 2015 album ‘Vulnicura’ was perhaps her most deeply personal, dealing directly with her breakup. ‘Stonemilker’ is a stunning, weird track that sees her baring her soul.

Saddest lyric: “Show me emotional respect/and I have emotional needs/I wish to synchronise our feelings

16. ‘Dying’ – Hole

Opening with Courtney Love’s whispers, ‘Dying’ is an uncharacteristically quiet Hole song that deals with the deep loss and grief she felt in the years after Kurt Cobain died.

Saddest lyric: “Remember, you promised me/I’m dying, I’m dying, please/I want to, I need to be/under your skin

17. ‘Sad Day’ – FKA Twigs

With glitchy, creepy beats and Twigs’ ethereal vocals, ‘Sad Day’ is a heartbreaking, otherworldly take on love and loss.
Saddest lyric: The city howls with a cry to seduce you/and claim you/so it’s time/and it’s a sad day for sure

18. ‘My Immortal’ – Evanescence

Evanescence’s heavy songs are fun, but ‘My Immortal’, which leans on Amy Lee’s incredible voice and piano, is still their most emotive track.

Saddest lyric: I’ve tried so hard to tell myself that you’re gone/but though you’re still with me, I’ve been alone all along

19. ‘Don’t Speak’ – No Doubt

Deviating from No Doubt’s ska roots, ‘Don’t Speak’, from 1995’s ‘Tragic Kingdom’, deals with Gwen Stefani’s painful breakup from bandmate Tony Kanal. It still goes hard.

Saddest lyric: “As we die, both you and I/with my head in my hands, I sit and cry

20. ‘Cranes in the Sky’ – Solange

Solange broke a lot of hearts with ‘A Seat at the Table’, and ‘Cranes in the Sky’ epitomises her devastating power, with haunting vocals and lyrics about trying to push pain away.


Saddest lyric: “I tried to let go my lover/thought if I was alone then maybe I could recover/to write it away or cry it away.”

21. ‘Liability’ – Lorde

Lorde’s 2017 album ‘Melodrama’ gave sad girls everywhere a lot of crying material for the coming months (or years). ‘Liability’, with its self-deprecating lyrics over soft piano, is still likely to set you off.

Saddest lyric: “The truth is I am a toy that people enjoy/’til all of the tricks don’t work anymore/and then they are bored of me

22. ‘when the party’s over’ – Billie Eilish

Billie Eilish was just 17 when her debut album, ‘When We All Fall Asleep, Where Do We Go?’ was released, but that didn’t stop her from exploring some pretty heavy feelings on it.

Saddest lyric:quiet when I’m comin’ home and I’m on my own/and I could lie, say I like it like that, like it like that

Sad Boys

23. ‘2:45am’ – Elliott Smith

There’s nothing like a late night walk to get the deep thoughts and memories flowing, and where possible, there’s nothing like Elliott Smith to guide you through it.

Saddest lyric:It’s 2:45 in the morning/and I’m putting myself on warning/for waking up in an unknown place/with a recollection you’ve half erased

24. ‘Salutations’ – Conor Oberst

Conor Oberst never kept his sad lyrics just for Bright Eyes, and ‘Salutations’, from the album of the same name is no exception.

Saddest lyric: “It’s hopeless/these rules make no sense/first they say we can’t be lovers/and now they say we can’t be friends

25. ‘Mesa, AZ’ – Bad Books

Manchester Orchestra and Kevin Devine’s project Bad Books deals with some pretty heavy topics, and ‘Mesa, AZ’ is a soft exploration of loss.

Saddest lyric:Every hurdle, every chasm, every shocking and unspeakable blow/just proves the universe is chaos, so you laugh to clear the lump from your throat

26. ‘23’ – Jimmy Eat World

Forget breakup songs – introspective songs about growing up will always hit so much harder, and Jimmy Eat World’s ‘23’ will forever take you to a reflective place.

Saddest lyric: Amazing still it seems/I’ll be twenty-three/I won’t always love what I’ll never have/I won’t always live in my regrets

27. ‘Hallelujah’ – Jeff Buckley

While Jeff Buckley didn’t write ‘Hallelujah’, he did do that with it. 

Saddest lyric: “She tied you to her kitchen chair/and she broke your throne and she cut your hair/and from your lips she drew the Hallelujah

28. ‘Hold Me Down’ – Motion City Soundtrack

‘Hold Me Down’ is Motion City Soundtrack’s most overtly melancholic song, dealing with the aftermath of a breakup and all the feelings that entails.

Saddest lyric:You’re the echoes of my everything/you’re the emptiness the whole world sings at night/you’re the laziness of afternoon

29. ‘Fingers’ – Lil Peep

Released posthumously after his tragic death, Lil Peep’s introspective ‘Fingers’ has a haunting prescience that’s hard to ignore.

Saddest lyric: “I’ll be the first there/and I’ll be the last there/I’m not gonna last here/I’m not gonna last long

30. ‘Lua’ – Bright Eyes

There are a lot – a lot – of sad Bright Eyes tracks. Some might say all of them. But ‘Lua’, with its acoustic guitar and Oberst’s gentle voice, is a deceptively quiet song about substance abuse and loneliness that would move anyone to tears.

Saddest lyric:It’s not something I would recommend/but it is one way to live/’cause what is simple in the moonlight/by the morning never is

31. ‘I Can Feel a Hot One’ – Manchester Orchestra

Traversing anxiety, addiction, religion and parenthood, ‘I Can Feel a Hot One’ is a moving song that, with the audible pain in singer Andy Hull’s voice, is heartbreaking every time. 

Saddest lyric:The Lord showed me dreams of my daughter/she was crying inside your stomach

32. ‘Are We Still Friends’ – Tyler, The Creator

On ‘Are We Still Friends’, the closing track on Tyler, the Creator’s most recent album ‘IGOR’, he shows a softer side, asking over and over again “are we still friends?” and building to an emotional climax featuring the iconic Al Green.

Saddest lyric:You’re caught in this matrix, don’t know where you’re playing/you made it, could be your favourite if you make it your friend

33. ‘I Just Want to Sell Out My Funeral’ – The Wonder Years

Perhaps the most moving (and genuinely good) pop punk song of all time, The Wonder Years’ seven-minute epic ‘I Just Want to Sell Out My Funeral’ deals with loss, grief and feelings of inadequacy.

Saddest lyric: I just want to sell out my funeral/I just want to be enough for everyone

34. ‘The District Sleeps Alone Tonight’ – The Postal Service

In Death Cab For Cutie, Ben Gibbard has broken plenty of hearts. Side project The Postal Service, however, is responsible for its own fair share.

Saddest lyric:I am finally seeing/that I was the one worth leaving

35. ‘For the Widows in Paradise, for the Fatherless in Ypsilanti’ – Sufjan Stevens

Sufjan Stevens’ upcoming album, ‘The Ascension’, is likely to hurt some feelings in September. ‘Widows’, which has of course featured on The O.C., is a lovely song that somehow makes even the banjo moving.

Saddest lyric:Like a father to impress/like a mother’s mourning dress/if we ever make a mess/I’ll do anything for you

36. ‘England’ – The National

The National’s back catalogue could have a list all to itself, but ‘England’ is a powerful song that builds over five and a half minutes, giving you more than enough time to cry.

Saddest lyric:Put an ocean and a river between everybody else/between everything, yourself and home

37. ‘I Will Follow You Into the Dark’ – Death Cab For Cutie

Much of Death Cab For Cutie’s album ‘Plans’ deals directly with death, but ‘I Will Follow You Into the Dark’ definitely prompts the most morbid reflection.

Saddest lyric:Love of mine, someday you will die/but I’ll be close behind/I’ll follow you into the dark

38. ‘White Ferrari’ – Frank Ocean

With ‘Blond’, Frank Ocean immediately became the softest boy. ‘White Ferrari’ is a tender, painful song about teen love.

Saddest lyric:I care for you still and I will forever/that was my part of the deal, honest

39. ‘I Sing I Swim’ – Seabear

‘I Sing I Swim’, by Icelandic band Seabear, is an idyllic song that just feels like nature. If you’re struggling with just being a person right now, it might make you feel a little more normal.

Saddest lyric: “Human skin can be hard to live in/you’ll feel better in the morning

40. ‘Fake Lighting’ – Pianos Become the Teeth

A complicated song about a complicated love, ‘Fake Lighting’ is open to interpretation – based entirely on what you’re going through, of course.

Saddest lyric:So come, confess something dire/and nothing less and hold your breath/so hang your head

41. ‘This is the Day’ – The The

A reflective, sometimes positive song on attempting to change (and perhaps the futility of it), ‘This is the Day’ deals with the relentless passing of time.

Saddest lyric: The side of you they’ll never see/is when you’re left alone with your memories/that hold your life together, like glue

42. ‘Nitrous Gas’ – Frightened Rabbit

Taking on a darker edge following Scott Hutchison’s death in 2018, he once called ‘Nitrous Gas’ an “exercise in writing the most miserable song possible,” which is accurate, but it is also very beautiful.

Saddest lyric:But if happiness won’t come to me/hand me the nitrous gas/you can keep all of your oxygen

43. ‘Wake Up’ – Arcade Fire

Getting to the heart of the real issues, Arcade Fire’s ‘Wake Up’ is a great one if you want to panic about getting older.

Saddest lyric:If the children don’t grow up/our bodies get bigger but our hearts get torn up

44. ‘Tears in the Rain’ – The Weeknd

While he’s often better known for party anthems, ‘Tears in the Rain’ the closer from The Weeknd’s debut album ‘Kiss Land’ is seven minutes of agonising ruminations on fame and love, topped off by those impossibly high, Prince-esque vocals.


Saddest lyric: “Embrace all that comes/and die with a smile/don’t show the world how alone you’ve become now”

45. ‘Emily’ – From First to Last

From screaming to Skrillex, Sonny Moore is a multi-faceted musician. On acoustic love song ‘Emily’ however, he brought it down a notch, giving emos in unrequited love something to cry to.

Saddest lyric: “Trapped by pretty eyes and letters for all time/the only thing that I’ve been waiting for

LEAVE A REPLY

Please enter your comment!
Please enter your name here