Playlist: The Saddest Songs Ever, According to Queer Cancers

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“Happy” Cancer season!!!! 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 a bunch of Cancers (and broadened the poll to include anyone Cancer risings and moons) to pick the saddest song ever. 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 — especially not in their own damn season!

I ended up receiving soooooo many songs covering a wide range of Cancer Sadness™ — from grief to heartbreak to loneliness to pain to death to loss to yearning to breakups to regret. You name it; Cancers will cry about it!

While listening through these decidedly somber tunes, I narrowed them down and tried to arrange them in a way that made narrative sense to me, an overthinking Taurus moon. This resulted in perhaps the greatest crying playlist of all time? See for yourself, and have a good cry along the way. It’s just under 90 minutes, which I think is the perfect amount of time to be in your feels. Scroll down for the Spotify playlist.

This post was originally written in 2022 and updated/republished in 2023.


cancer season playlist

  1. “Swim Good” by Frank Ocean
  2. “Something in the Way” by Nirvana
  3. “I Bet On Losing Dogs” by Mitski
  4. “The Glow, Pt. 2” by The Microphones
  5. “Silver Springs” by Fleetwood Mac
  6. “Promise” by Julia Nunes
  7. “Your Love Is Killing Me” by Sharon Van Etten
  8. “Sullen Girl” by Fiona Apple
  9. “Kiss” by Scout Niblett feat. Bonnie “Prince” Billy
  10. “Cry, Cry, Baby” by Nina Nastasia
  11. “Where Do Broken Hearts Go” by Whitney Houston
  12. “Hurt” by Johnny Cash
  13. “Ride” by Lana Del Rey
  14. “Bones” by Mod Sun
  15. “I Want You” by Mitski
  16. “All Alright” by Sigur Rós
  17. “Dark Come Soon” by Tegan and Sara
  18. “If U Love Me Now” by MUNA
  19. “Ev’ry Time We Say Goodbye” by Ella Fitzgerald
  20. “One More Hour” by Sleater-Kinney

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

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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 Orlando. 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 863 articles for us.

35 Comments

  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. Love this article!! Someone mentioned Sufjan’s Casimir Pulaski Day already, which is my top song for crying to, but also The Night We Met by Lord Huron and St Jude by Florence + the Machine

  6. 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.

    • “Puff the magic dragon” is devastating! It also gave me Feelings as a child, and honestly I feel like that’s the perfect summary of who I was as a kid. I spent a lot of time very sad about things that had never existed – or at least not in my little life.

    • hahaha yes, right down to the age of onset (pisces sun/cancer rising). can i add the rainbow connection to this song cluster, because???? it gets me every. single. time.

  7. 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

  8. Gemini, but I have one to contribute.

    I’ve been listening to “My Immortal” by Evanescence lately. Every time I do I see a montage of Shauna’s life after getting back from the Wilderness. Marrying Jeff, giving birth to Callie, raising her, and her domestic life of oblivion. Over it all Jackie is hovering. A constant presence, felt but never seen. Shauna can never escape her need for Jackie, no matter how many years pass.

  9. My chart is FULL of Cancer (sun, rising, Venus, Mercury) and I can’t relate to this “Cancer = sad/feelings” business at all! I’m the most consistently joyful person I know! Is it because of the Gemini moon?!?

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