We talk a lot about sob-inducing movies, but personally, I don’t think enough attention is paid to the power of music that makes you cry, from Adele ballads—duh—to offerings from Mitski and Enya (trust me on that one). After the emotional few years we’ve all had, it’s more important than ever to let yourself feel your feelings, as trite as that may sound, and sometimes, you need a little help.
Here, in no particular order (other than the one they occurred to me in), are 23 of the very best songs to curl up and weep to.
23. “Echoes in Rain” by Enya
Trust me, if you need a good weep, listen to this song while hungover. The plaintive chorus of hallelujahs is sure to get your tear ducts working when you’re in an already-weakened state.
22. “The Book of Love” by Peter Gabriel
Immortalized by the Scrubs finale, this song hits particularly hard if you just so happen to be single. Oof.
21. “Class of 2013” by Mitski
With lyrics like “Mom, am I still young? / Can I dream for a few months more?” this song is guaranteed to have you thinking about your own mother and crying hysterically.
20. “Hallelujah” by Jeff Buckley
Purists might prefer the Leonard Cohen original, but personally, I think this one is even more heartrending.
19. “Someone Like You” by Adele
I mean, do I even have to say anything here? It’s Adele.
18. “Bite the Hand” by boygenius
Not for nothing, the lyrics “I can’t love you how you want me to,” wistfully sung by the supergroup trio of Lucy Dacus, Phoebe Bridgers, and Julien Baker, have gotten me through four consecutive breakups.
17. “Lavender Burning” by Half Waif
From its opening notes, this ode to leaving a place (or person) behind when you’re not quite ready to is an absolute gut-punch (in the best way possible).
16. “Divorce Song” by Liz Phair
In just over three minutes, Phair manages to capture the agony and discomfort of a relationship that’s just beginning to sour.
15. “I Can’t Make You Love Me” by Bonnie Raitt
Oh, Bonnie. True story: I once cried to this song so loudly on an Amtrak that the conductor came over to see if I was okay.
14. “I Know the End” by Phoebe Bridgers
It’s hard to find a Phoebe Bridgers song that doesn’t make everyone in the immediate vicinity tear up, but this one is perhaps the most moving on her latest album, Punisher.
13. “Breathe Me” by Sia
Four words: Six Feet Under finale. I will never be the same.
12. “Empty Hearted Town” by Warren Zevon
Those lyrics! “I’m walking down the sidewalks of L.A. / Wishing I had a warmer jacket / And the leaves are falling down.” So simple, yet so profoundly sad.
11. “I Think It’s Going To Rain Today” by Nina Simone
The Randy Newman original is no less mournful, but you just can’t beat Ms. Simone’s vocals for crying content (“cryntent”?).
10. “My Mother & I” by Lucy Dacus
Has there ever been a more poignant summary of the mother/daughter relationship than “My mother hates her body / We share the same outline / She swears that she loves mine”?
9. “Normal Girl” by SZA
This song about contorting yourself to be what someone else wants, even as you know you’ll never quite get it right, always gets me.
8. “Heavy Balloon” by Fiona Apple
Unless you want me to flash back to the early days of the pandemic and sob for 10 hours, do not play any song from Fetch the Bolt Cutters for me.
7. “River” by Joni Mitchell
There’s a reason Jess from New Girl plays this song on a loop after a breakup; it’s about as cathartic as music gets.
6. “Leaving on a Jet Plane” by John Denver
Extreme “crying in the dining hall on the last day of summer camp” vibes here.
5. “Ex-Factor” by Lauryn Hill
There’s no R&B breakup anthem quite like this one, and it’s guaranteed to at least get you on your way to closure.
4. “We Were Happy” by Taylor Swift
No way would this list be complete without a Swift banger or two, and this one is a particularly forlorn ode to lost love.
3. “Jolene” by Dolly Parton
Yes, this song has a beat that might belie its heartbreaking core, but it’s essentially one woman begging another not to steal her man. What could be sadder?
2. “Heartbeat” by Beyoncé
Beyoncé wrote this song after experiencing a miscarriage, and accordingly, it’s a brutal yet beautiful listen.
1. “Fast Car” by Tracy Chapman
Yes, I’m gay. Any questions?
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