We talk a lot about sob-inducing movies, but personally, I don’t think enough attention is paid to the best sad songs to cry to, from Adele ballads—duh—to offerings from Mitski and Enya (trust me on the latter).
After the year we’ve all had, it’s more important than ever to let yourself feel your feelings, as trite as that may sound. Leave it to these 35 songs to help you set the right mood.
“To Be Loved” by Adele
Adele knows her way around a shattering piano ballad—see: “Someone Like You,” “All I Ask,” her version of “Make You Feel My Love”—but “To Be Loved,” the penultimate song on her 2021 album, 30, represents some of her most moving and confessional work to date. While she has, quite wisely, vowed never to perform the song in public (“I’ve only really sung it a few times and definitely can’t even really listen to it without getting emotional,” the singer admitted in an interview after 30 came out), she did post an astonishing live version of it to Instagram. Watch and weep!
“Love Is a Losing Game - Original Demo” by Amy Winehouse
Gorgeously spare, this early version of a standout from Winehouse’s Grammy-winning sophomre album, Back to Black, foregrounds the song’s plaintive, poetic lyrics: “Self-professed, profound / ’Til the chips were down / Know you’re a gambling man / Love is a losing hand…”
“Boston” by Augustana
There’s a reason this song turned up in One Tree Hill, Scrubs, and The Big Bang Theory; its thrashing, pop-punk sound, coupled with Dan Layus’s melancholic lyrics about a person longing to start over, cut to the quick. All together now: You don’t now me, and you don’t even care!
“The Luckiest” by Ben Folds
Ben Folds knows how to write a love song about serendipity and yearning—and this one was specifically for his wedding day. Like, c’mon!
“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.
“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.
“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—especially when you’re in an already-compromised state.
“Tears in Heaven” by Eric Clapton
The ballad hits particularly hard for anyone who’s lost a loved one too soon; Clapton wrote it in honor of his son who passed away.
“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).
“Sign of the Times” by Harry Styles
The song opens with “Just stop your crying,” but I need to play it at least three times before I can calm down.
“Uknown / Nth” by Hozier
Leave it to your favorite Irish singer-songwriter to “Sha-la-la” you through any heartbreak.
“Hallelujah” by Jeff Buckley
Purists might prefer the Leonard Cohen original, but personally, I think this one is even more heartrending.
“Leaving on a Jet Plane” by John Denver
Extreme “crying in the dining hall on the last day of summer camp” vibes here.
“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 moving as music gets.
“Ex-Factor” by Lauryn Hill
It could all be so simple, but you’d rather make it hard! One of the all-time great songs about a complicated, painful, but ultimately necessary split.
“River” by Leon Bridges
Leon Bridges’s voice is unspeakably moving, and “River” is a gospel song that perfectly captures what it feels like to wade through struggle, only to find what you need to push through and survive.
“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.
“ceilings” by Lizzy McAlpine
Was this one a bit overused on TikTok? For sure. But something about Lizzy McAlpine’s feathery voice, singing about a love story that goes from feeling like “the start of a movie I’ve seen before” to a figment of her imagination, absolutely wrecks me—not to mention the scenic music video that goes with it.
“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”?
“Class of 2013” by Mitski
Speaking of songs about mothers and daughters: With lyrics like “Mom, am I still young? / Can I dream for a few months more?” this song is also guaranteed to have you thinking about your own parent and crying hysterically.
“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”?).
“You’re Gonna Go Far” by Noah Kahan
Noah Kahan’s folk tunes can make anyone feel like they grew up on the grey, slushy roads of a New England town. This one’s for those who’ve left home and may be afraid to look back.
“Being Alive” by Dean Jones
A musical theater legend nonpareil, Stephen Sondheim crafted an oeuvre chock-full of gorgeous numbers (see: “I Remember” from Evening Primrose, “Losing My Mind” from Follies, “Send in the Clowns” from A Little Night Music, “Joanna” from Sweeney Todd, “Sunday” from Sunday in the Park with George, “Loving You” from Passion…), but the naked longing of “Being Alive,” the final song in Company deserves a special mention. “Somebody crowd me with love, somebody force me to care…” (Adam Driver’s long, shaky exhale after singing it in Marriage Story sort of says it all.)
“lacy” by Olivia Rodrigo
Olivia Rodrigo’s sophomore album, Guts, featured a number of instantly iconic songs, but “lacy” is perfect for playing in your car while sitting in a parking lot as the sun sets at 4:18 pm. (Follow it up with Rodrigo's “all-american bitch,” however, and you’ll soon be wiping those tears away.)
“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.
“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 Punisher.
“High and Dry” by Radiohead
I love “Creep,” but just take a look at these lyrics from “High and Dry”: “You broke another mirror / You’re turning into something you are not.” Jeez!
“Everybody Hurts” by R.E.M.
Sometimes, when the day is long and you’ve simply had enough, r.e.m knows exactly how to put that feeling into words. It’s a classic crying song for a reason.
“Gravity” by Sara Bareilles
One of the great piano ballads of its era, “Gravity” had adorably relatable origins: “‘Gravity’ was born out of a high school relationship falling apart and me being a drama queen about it,” Bareilles explained in 2019. “It’s talking about that first real heartbreak where you’re like, ‘I don’t think I’m gonna ever get over this,’ then of course eventually you do.”
“Breathe Me” by Sia
Four words: Six Feet Under finale. I will never be the same.
“Heaven Knows I’m Miserable Now” by The Smiths
Sometimes the very saddest songs are ironically upbeat. In this classic from the Smiths, the satisfying thrum of the melody is juxtaposed with lyrics like, “Why do I smile / At people who I’d much rather kick in the eye?” You’ll hurt, but you’ll hurt in a way that feels good.
“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.
“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.
“Empty Hearted Town” by Warren Zevon
Those lyrics! “I’m walking down the sidewalks of LA / Wishing I had a warmer jacket / And the leaves are falling down.” So simple, yet so profoundly sad.
“I Will Always Love You” by Whitney Houston
With all due respect to Dolly, there’s almost nothing more cathartic than scream-singing the final chorus of Whitney’s version.
