Playlist: It’s Sad, So Sad

Gloomy greetings from Sydney, where it’s winter and it’s been raining relentlessly and I’ve got a cold and everything is total misery. I’m just so SAD, you guys. While the Australian thing to do would be to harden the fuck up, instead I’ve chosen deal with my winter blues by hiding away in my emo cave, wallowing to the saddest songs ever until my heart drops out of my chest again and again. Some of those songs are below. Others have been contributed by Laneia and Katie.


It’s Sad, So Sad


Sorrow – The National
Street Spirit (Fade Out) – Radiohead
Bruised Orange (Chain of Sorrow) (John Prine cover) – Bon Iver
Blackbird – The Beatles
Candy Says – The Velvet Underground
The Darkest Side – The Middle East
I Love You, But I Don’t Trust You Anymore (Prince cover) – Holly Miranda
Killing Me Softly – The Fugees
Between the Bars – Elliott Smith
Transatlanticism – Death Cab For Cutie
The Child Is Gone – Fiona Apple
Other Towns and Cities – Camera Obscura
A Picture Of Our Torn Up Praise – Phosphorescent
Flightless Bird, American Mouth – Iron & Wine
Nothing Compares 2 U (Prince cover) – Sinead O’Connor
Sorry Seems To Be The Hardest Word – Elton John
Isn’t It A Pity (George Harrison cover) – Nina Simone
I Can’t Take It – Tegan and Sara
What If You – Joshua Radin
A Case Of You – Joni Mitchell
Almost Lover – A Fine Frenzy
The Blower’s Daughter – Damien Rice
Sleeper 1972 – Manchester Orchestra
Behind The Wall – Tracy Chapman

It’s Sad, So Sad from Autostraddle on 8tracks Radio.

What are your favourite sad songs? Hit us with them in the comments below.

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Crystal has written 320 articles for us.


  1. These song choices are great. I will add them to my playlist for those times when crying is cathartic. A few other ones:

    Brick – Ben Folds
    Already Dead – Beck
    No Surprises – Radiohead
    Anthrax – Kimya Dawson
    Josephine – Brandi Carlile

  2. OMG what a depressingly good list. I would probably add “Brick” by Ben Folds Five on there. Total tearjerker.

    Also, to date me a little bit, “Wind Beneath My Wing” is a classic but that’s really because I can’t hear it without thinking of the movies Beaches… one of the only movies where I could not stop crying. Damn you Bette Midler.

    If you all will excuse me, I need to go dim the lights, grab some Ben & Jerrys, put on my Spotify and compose myself.

  3. Good playlist. Where was this last week when I was so so sad?

    Also, these songs are good for wallowing in misery:

    Perth – Bon Iver
    9 Crimes – Damien Rice
    Samson – Regina Spektor
    Chasing Cars – Snow Patrol (What? You try listening to it in a certain mood, and see if it don’t put you further down there)
    Whiskey Lullaby – Allison Krauss (If you were to deal with that sadness with alcohol. Drinking alone is a surefire way to make yourself a little sadder)
    Can’t Go Back Now – Weepies (If say you were unreasonably sad about a past event/lover/place/home)

  4. *falls slowly in a circle, crying*
    Where was this last week when I was all about that melancholy life?

    “Somedays” – Regina Spektor
    “Where I Stood” – Missy Higgins
    “Taking in Water” – Jessie Ware
    “With Every Heartbeat (acoustic)” – Robyn
    “These Days” – Nico
    “I Can’t Make You Love Me” – literally anyone, I don’t care, I will cry

      • I used to listen to that song on repeat in high school when I was sad, which was all the time, and it reminded me that some days are shit and there’s nothing you can do about it, so I basically credit Regina with getting me through my teenage years.

        Also, the “I’m in love with your daughter/I wanna have her baby” bit was always intriguing to me back then, and then when I revisited the song in my twenties, I was like, “DUUUUUUH teenage me.”

  5. My two cents:

    My Body Is A Cage – Arcade Fire
    SRXT – Bloc Party
    Spanish Sahara – Foals
    Tracy – Mogwai
    How Disappear Completely – Radiohead

    but really everything I just said is irrelevant because I don’t think there could possibly be a more heartbreakingly sad song than “Biko” by Bloc Party.

  6. I have a Spotify playlist just for these occasions. It includes:
    Family – Noah Gunderson
    Set the Fire to the Third Bar – Snow Patrol and Martha Wainwright
    10,000 Miles – Mary Chapin Carpenter
    Try – Suzanna Choffel
    Don’t Think Twice, It’s All Right – Ke$ha
    Broadripple is Burning – Margot & The Nuclear So-and-So’s
    Welcome Home, Son – Radical Face
    I Was Broken – Marcus Foster
    The Fear – Ben Howard
    Let Her Go – Passenger
    1957 – Milo Greene
    Atlas Hands – Benjamin Francis Leftwich
    Blood Bank – Bon Iver
    Rivers & Roads – The Head & The Heart
    In My Veins – Andrew Belle
    The War is Over – Kelly Clarkson
    Antes De Las Seis – Shakira
    Time – Hans Zimmer
    So Long, Lonesome – Explosions in the Sky
    How It Ends – DeVotchKa
    Mary May & Bobby – Joe Purdy
    Sweet Lorraine – Patty Griffin
    Mary – Patty Griffin
    Hurt – Johnny Cash

    And, of course, a selection of melodrama by Brandi Carlile, The Lumineers, The Fray Missy Higgins, Leonard Cohen, Mary Lambert, Daughter, and Andrea Gibson.

  7. When I was in high school, my “have a good cry” playlist was anchored by Liz Phair’s “Ant in Alaska.”

    I also cry to Taylor Swift generally (and celebrate to Taylor Swift, drive to Taylor Swift – I’m talking 125+ miles of “Treacherous” on repeat yesterday, fall asleep to Taylor Swift, etc.) because she has mastered eliciting all the feels.

  8. Melbourne is being its usual indecisive self, but this a fantastic playlist for when the sun goes away and hides and it gets all rainy and cold again.
    Also The Call- Regina Spektor, all the melancholy feels

  9. OMG I totally get this. I’ve been diagnosed with seasonal affective disorder, but it exists… only in summer. I think it’s because I’m in terribly awful hot area of California. Far enough away from the beach that we get no coastal wind, just scorching awful heat. That makes you stay inside all day with the blinds drawn. I think I actually go outside more in the winter.
    Never move to Riverside county if you hate living in hotter-than-shit conditions.

  10. This is great. I had a “sad songs” and a “dear kippikins, i think you might be homesick” playlist while I was on the east coast with a couple of these songs. Glad I’m not alone in my winter cave wallowing ways. Stay strong! :)

  11. how can we namecheck regina spektor and not bring up “laughing with.”


    also blink-182 (lovestruck mopey latter-day blink, not juvenile pun blink, not that there’s anything wrong with that) and robert smith, “all of this.” robert smith, youguise, for srs, can’t get much more melancholy than that

  12. Case of You is one of my top 5 songs of all time! Such an amazing piece of music! They sure don’t make em’ like they used too! Side Note: Joni Mitchell grew up in Saskatoon saskatchewan, only 2.5hrs from where I live! Pretty neat! prairie pride!

  13. Don’t Forget Me- Neko Case (originally by Harry Nilsson)
    Cologne- Ben Folds
    Walk Away- Ben Harper
    Vulnerable- Juanes
    Smoke- Natalie Imbruglia
    Strange Fruit- Billie Holiday
    Gardenia- Mandy Moore
    Bad Religion- Frank Ocean
    Fruit Tree- Nick Drake
    This Time Won’t You Save Me- Nicki Minaj

    I could go on for.ev.errrrrr (Sandlot voice), but instead I’m going to crank up some comedy this week and laugh at Wanda Sykes instead of sobbing profusely.

  14. Gravity by Sara Bareilles kills me every damn time. Especially the live version.
    Honorable mentions:
    Can’t Let Go by Landon Pigg
    Where I stood by Missy Higgins
    Video Games by Lana Del Rey
    Sunday Morning by Travis Garland
    Give Me Love by Rd Sheeran
    “Nothing Lasts Forever” and “She Will be Loved” by Maroon 5
    Distance by Christina Perri
    I Never Told You by Colbie Caillat

    The list goes on and on

  15. One of the saddest songs I know is probably “Poison Oak” by Bright Eyes – the complete “I’m Wide Awake It’s Morning” album is very sad, but “Poison Oak” always makes me cry.
    Also good: Kat Frankie’s song “Happy” (despite its title a very, very sad song).
    And, of course, almost every song by Antony and the Johnsons.

  16. I listen to the sadcore hibernation playlist on songza like daily. My favorite sad song is probably Drag by Low or How to Disappear Completely by Radiohead.

    Also, I have a playlist in my iTunes entitled ‘Despair’ (because I’m dramatic like that) and like almost the whole ‘The Con’ album by Tegan and Sara is on it.

  17. A selection from my own sad/moody playlist:

    “Trouble” – Cat Stevens
    “Unhook the Stars” – Cyndi Lauper
    “Doll Parts” – Hole
    “Try Again” – Keane
    “The District Sleeps Alone Tonight” – The Postal Service
    “Let Down” – Radiohead
    “Stuck in a Moment You Can’t Get Out of” – U2
    “Delicate” – Damien Rice

  18. Heron Blue by Sun Kil Moon always gets me in a sad mood, and Mad World by Gary Jules. Or maybe that’s cause they were both used in Gears of War trailers and I just have so many sad feelings when it comes to Gears of War.

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