Playlist: The Saddest Songs Ever, According to Cancers

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Remember when I made all my friends mad at me by asking them to pick just ONE song as the most romantic song of all time? Well, I’m back as an agent of musical chaos, baby! This time, I made a lot of people with a lot of feelings have…a lot of feelings. Specifically, I asked Cancers (and broadened the poll to include anyone Cancer risings and moons) to pick the saddest song ever. As with last time, people became a little too stressed about sticking to one song, so I did amend the rules slightly, as I did not want to be the cause of a Cancer’s meltdown. I ended up receiving over 30 songs covering grief, heartbreak, loneliness, pain, death, loss, you name it! I spent an entire afternoon listening to the songs while writing (I have no Cancer in my chart, but I have been often described as a Sad Bitch because of my preference for depressing art). I ended up picking 15 of my favorites and compiling them here!

This resulted in perhaps the greatest crying playlist of all time? See for yourself!

Sad Cancerian Bops

  1. “I Bet On Losing Dogs” by Mitski
  2. “The Glow, Pt. 2” by The Microphones
  3. “Silver Springs” by Fleetwood Mac
  4. “Promise” by Julia Nunes
  5. “Your Love Is Killing Me” by Sharon Van Etten
  6. “Sullen Girl” by Fiona Apple
  7. “Kiss” by Scout Niblett feat. Bonnie “Prince” Billy
  8. “Cry, Cry, Baby” by Nina Nastasia
  9. “Hurt” by Johnny Cash
  10. “Ride” by Lana Del Rey
  11. “Bones” by Mod Sun
  12. “I Want You” by Mitski
  13. “All Alright” by Sigur Rós
  14. “Dark Come Soon” by Tegan and Sara
  15. “If U Love Me Now” by MUNA

You don’t have to have any Cancer in your chart to know the power of a good cry-song. What’s your top sad tune?

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Miami. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 507 articles for us.


  1. Kate Bush, Moments of Pleasure. Concrete Blonde’s Take Me Home. Cyndi Lauper singing Sally’s Pigeons. Paloma Negra, as done by Chavela Vargas. And, oddly, She’s An Angel by They Might Be Giants kills me every time the slide guitar starts in.

  2. Winter by Tori Amos.
    Sellers of Flowers by Regina Spektor.
    Any song with the bittersweet flavor of childhood and memories.

    The one song I can’t hear without silently singing along and crying to is You Are My Sunshine. My grandma used to play it to tune up her guitar and it struck me as hauntingly sad then. Now interlaced with memories of her, I find it heartbreaking.

  3. I do not have any Cancer in my chart, but I am an enneagram 4 so indulging in sadness greatly appeals to me. I have a Spotify playlist called Perfectly Melancholy that will definitely be expanding thanks to y’all’s recommendations.

  4. Super sensitive cancer here! “Smile” by Portugal. The Man, “Can’t Help Falling in Love” by Elvis, and “Sea of Love” by Cat Power make me a sloppy, sad mess when I’m already melancholy. None of them are particularly sad songs, but they hit me right in my feels every time.

  5. Ok this one might sound a bit nuts but the last verse of “puff the magic dragon” sets me off. It did the very first time I heard it when I was like 6 years old and I never recovered.

    I’m a double cancer. This might be relevant.

  6. Cancer sun/Venus here! the last song I fully cried to (before reading this article) was “I Guess” by Mitski :’) “Two Slow Dancers” is another good one

    for a real double whammy of Sad Girl/Sad Boy Music, I love Julien Baker’s cover of “Ballad of Big Nothing” by Elliott Smith

    and “It’s Okay” by Land of Talk and “Bar on A” by Greg Holden always get me

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