55 Saddest Love Songs of All Time, If You're in Need of a Cathartic Cry

We all enjoy a celebratory and, dare we say it, slightly sappy love song that revels in the beauty of human connection. But sometimes the track that really hits home is more somber.

Some of the sad love songs in this collection have the capacity to make you cry, and may even help you mend a broken heart after a breakup. A handful of '90s classics (Whitney Houston's "I Will Always Love You," Toni Braxton's "Un-Break My Heart") and R&B hits are on the list, as are sweeter numbers that would be at home on a Valentine's Day playlist if you're spending the holiday solo. Many sift through the rubble of past relationships (Drake's "Marvin's Room," Lauryn Hill's "Ex-Factor"), while others are about the momentary relief of connection, even if you know it's not with the right person (Sam Smith's "Stay With Me," Bonnie Raitt's, "I Can't Make You Love Me"). And emotional classics by Joni Mitchell, Carole King, and Fleetwood Mac prove that while sonic style and songwriting changes over the decades, the raw feeling of heartbreak will always be relatable.

You may be trying to rekindle a smothered spark, dealing with quarantine-related long distance drama, or struggling with keeping your dating life going this winter. Whatever's causing you strife, we hope you'll find catharsis in one of these sad love songs.

amazon.com

$1.29

LISTEN NOW

Adele is the patron saint of powerhouse ballads, and "Someone Like You" ranks up there with her very best. Adele's voice can soar on top of a 30-piece orchestra, but here she's accompanied by a simple piano part as she addresses an ex who has moved on and found new love.

amazon.com

$1.29

LISTEN NOW

The intra-band romantic drama that fueled Fleetwood Mac's historic Rumors record is well documented, but even before its 1977 release, they were penning love songs that stuck to your ribs. One such track was "Landslide," a gorgeous, lilting showcase for singer Stevie Nicks about how love, in all its forms, never stays static.

amazon.com

$1.29

LISTEN NOW

Taylor Swift has mined the details of her own romantic life to great success, but on Lover's "Death by a Thousand Cuts" she switched her approach, drawing inspiration from the Netflix rom-com Someone Great.

The track itself is vintage Swift. She fills the twinkling Jack Antonoff production with vivid imagery–haunted clubs, boarded up windows, and harsh hungover mornings. "Death by a Thousand Cuts" captures the true aftermath of a breakup, and the way the pain comes in small, unexpected ways, not necessarily all at once.

amazon.com

$1.29

LISTEN NOW

Anytime a song can be distinguished by a single note, you know that it's made an impact. Whitney Houston's cover of Dolly Parton's "I Will Always Love You," which appeared on The Bodyguard soundtrack, is one of the 20th century's defining ballads. Houston kept the methodical pacing of Parton's original, but turned it into a simmering slow jam that fit perfectly into the '90s trend of moody, glacial radio hits.

Even when you know exactly what the song is building up to, the moment where Houston hits that sky-scraping note on the final hook, always feels stirring.

amazon.com

$1.29

LISTEN NOW

Bonnie Raitt's 1991 heartbreaker "I Can't Make You Love Me" is considered to be among the best songs ever written. Raitt makes the lyrics, written by Mike Reid and Allen Shamblin, absolutely jump off the page, turning the song into a tearjerker about accepting that you can't change the way another person feels inside.

"'Cause I can't make you love me if you don't / You can't make your heart feel something it won't," she sings.

amazon.com

$1.29

LISTEN NOW

Carole King's landmark 1971 album Tapestry is filled with gorgeous, poignant songs about heartbreak brought to life through King's vivid lyricism. "It's Too Late" was one of the album's most popular tracks. It captures the point at the end of a relationship where there simply isn't much left to say. Both people have tried their best, but it's just not meant to be.

"There'll be good times again for me and you / But we just can't stay together, don't you feel it, too," she sings.

amazon.com

$1.29

LISTEN NOW

The title track of Lizzo's breakout album sees the multitalented musician indulging her inner diva. From the opening line, she's belting as powerfully as she ever has, channeling the spirit of Aretha and Whitney. Much of Lizzo's music explores her own sense of self-worth and independence, but on "Cuz I Love You" she opens up about what she'll do for love.

"Got me standing in the rain / Gotta get my hair pressed again / I would do it for you all, my friend," she promises.

amazon.com

$1.29

LISETN NOW

Rihanna's 2016 opus ANTI smartly stripped away much of the gloss and glitz of pop superstardom, giving her more room to emote as a vocalist. That produced several powerful tracks ("Higher," "Love on the Brain," "Needed Me"), as well as "Close to You," a moving piano song about a relationship crumbling in slow motion that plays like a sequel to 2012's "Stay."

"Nothing but a tear, that's all for breakfast / Watching you pretend you're unaffected," she sings.

amazon.com

$1.29

LISTEN NOW

Inspired by Saul Bellow's Henderson the Rain King, Joni Mitchell's "Both Sides Now" is an ode to shifting perspectives and to understanding someone's motivations that were previously alien to you. As with Mitchell's best music, it's depicted through gorgeous nature imagery–clouds that look like "ice cream castles," and "angel hair"–and sung in her delicate, lilting cadence.

amazon.com

$0.99

LISTEN NOW

From the climate crisis to the casualties of drone strikes in the Middle East, ANOHNI has a gift for using the style and structure of dance music to tell urgent stories. "I Don't Love You Anymore" is relatively straightforward–even its video is simply a six-minute shot of the singer–but her voice is so stunning and wounded that you hang on every word.

"You left me in a cage / My only defense was rage," she sings, her voice curling into a slight snarl, mimicking the way heartbreak so often hardens into anger.

amazon.com

$1.29

LISTEN NOW

Sam Smith has written plenty of songs about the bluer side of romance, but their hit single "Stay With Me" goes to a different place. The track is somewhere between booze-fueled longing and sober honesty. Smith knows that the connection they share with the song's subject is nothing like true love, but still a favorable alternative to isolation.

"Deep down I know this never works / But you can lay with me so it doesn't hurt," they plead.

amazon.com

$1.29

LISTEN NOW

John Mayer's "Dreaming With a Broken Heart" morphs from a delicate piano ballad to chugging blues rock jam, showcasing the breadth of Mayer's talent that made him such a star throughout the '00s. His breathy, raspy voice is uniquely suited for songs like this: smooth and sultry, but emotional on the surface.

amazon.com

$1.29

LISTEN NOW

With the help of producer Salaam Remi, Amy Winehouse made "Tears Dry on Their Own," a modern spin on the long lineage of Motown's sad love songs. It even flips Marvin Gaye and Tami Terrell's "Ain't No Mountain High Enough."

Winehouse's smoky, velvet-lined jazz club voice is put to great use here, restrained and conversational on the verses, gradually swelling in volume and tone on the hook to match the song's horns.

amazon.com

$1.29

LISTEN NOW

Johnny Cash originally penned "Give My Love to Rose" back in 1957, but it proved to be such a staple of his catalog that he rerecorded it multiple times, including for his 2002 record American IV: The Man Comes Around.

The track is vintage Cash. It's a masterclass in storytelling, as he stumbles upon a dying man by the railroad tracks who, in his final moments, tells Cash to go see his beloved Rose and their son. He even expresses that he wants his wife to find a new person to love.

"Tell my Rose to try to find another / 'Cause it ain't right that she should live alone," Cash sings.

amazon.com

$0.99

LISTEN NOW

There are approximately 1 million covers of Bon Iver's "Skinny Love," but none of them hit your gut quite like the original (Birdy's piano-powered take comes closest). The song, which helped turn Bon Iver into an indie phenomenon, is minimalist in its presentation, but cinematic in emotional scope. Throughout, Vernon's voice croaks and breaks, as if he's struggling to get the words out.

"You're in a relationship because you need help, but that's not necessarily why you should be in a relationship. And that's skinny. It doesn't have weight," Bon Iver's Justin Vernon told Pitchfork about the song. "Skinny love doesn't have a chance because it's not nourished.

amazon.com

$1.29

LISTEN NOW

Beyoncé set aside the delicate love songs with "Irreplaceable," a chart-topping ode to knowing your worth and not letting anyone try to lower it. The song plays as a prelude to some of her meatier work on Beyoncé and Lemonade, and sees her sending an unfaithful former flame out the door expeditiously.

"Rollin' her 'round in the car that I bought you / Baby, drop them keys / Hurry up before your taxi leaves," Beyoncé warns.

amazon.com

$1.29

LISTEN NOW

On "Drew Barrymore," SZA gets all psyched up to see someone at a party, only to find that they showed up with another girl. The song captures the whiplash of butterflies turning to stone in your stomach, as she sings achingly about how sometimes romance and disappointment can feel as linked as hangovers and alcohol.

"It's hard enough you got to treat me like this / Lonely enough to let you treat me like this," SZA laments.

amazon.com

$1.29

LISTEN NOW

Written by Chris Martin as a tribute to his then-wife, Gwyneth Paltrow's late father, "Fix You" is one of Coldplay's most affecting songs in a discography filled with enough tearjerkers to flood a stadium. Though the song primarily deals with death and moving on from that kind of loss, its lyrics are easy to graft onto a romance.

amazon.com

$1.29

LISTEN NOW

Few A-listers are as good at lost love ballads as Bruno Mars, who has topped charts and made eyes water with songs like "Talking to the Moon," "It Will Rain," and "When I Was Your Man." The latter is perhaps the best of the lot, inspired by '70s piano ballads like The Commodores' "Still," and featuring one of Mars' most searing hooks.

"I should have bought you flowers / And held your hand / Should have gave you all my hours / When I had the chance," he laments.

amazon.com

$1.29

LISTEN NOW

Back in the early '60s, Diana Ross and The Supremes' three other core vocalists were just teenagers, but they could capture the feeling of a lifetime's worth of heartbreak on records like "Play a Sad Song." Penned by Motown mastermind Berry Gordy, the track has cinematic horns and strings that serve as a fitting backdrop for the intertwined harmonies of these preternaturally gifted young vocalists.

amazon.com

$1.29

LISTEN NOW

Say Anything's "Alive With the Glory of Love" bristles not just with the urgency and desperation of young love, but because of its chilling backdrop. The song is about the relationship between singer Max Bemis' grandparents, who are Holocaust survivors, and their time hiding from the nazis.

amazon.com

$1.29

LISTEN NOW

The '90s were the golden era of slow jam ballads, and only a few songs captured that crying-in-a-rainstorm melodrama as well as Toni Braxton's "Un-Break My Heart."

The song clearly resonated with a lot of jilted listeners, as it was named one of the 20 biggest Hot 100 hits of all time in 2018.

amazon.com

$0.89

LISTEN NOW

Yellow Days' George van den Broek was just 17 when he broke through with "Your Hand Holding Mine," but that's hard to guess by the sound of his voice. Van den Broek has a commanding baritone, often likened to fellow alt outsider King Krule.

amazon.com

$1.29

LISTEN NOW

A quintessential '80s power ballad, what Poison's "Every Rose Has Its Thorn" lacks in subtlety it more than makes up for with heart-on-the-sleeve candor. Long before his reality show renaissance, Bret Michaels was giving his all to this raw chart-topper.

amazon.com

$1.29

LISTEN NOW

Long before he was an A-lister big enough to headline the Super Bowl, The Weeknd was a mysterious figure in the nascent Toronto music scene, writing songs about excess and infidelity that sounded like the aftermath of a post-breakup bender.

His first major hit was "Wicked Games," a fiery track about wounded people finding solace in each other and hurting their actual partners in the process. It's a powerful showcase for The Weeknd's crystalline tenor, which seems to float a thousand feet above the instrumentals muddy guitar and bass.

amazon.com

$1.29

Listen Now

Most somber love songs come from a singular perspective: I'm hurt. I don't love you anymore. I don't want to be alone. What makes Gotye and Kimbra's "Somebody That I Used to Know" so singular and enduring is that it offers both perspectives on a failed relationship, shifting vantage points in the middle to remind us that even though we may demonize an ex, we're rarely free of blame.

And the song clearly resonated with fans, becoming one of the most successful Hot 100 entries ever, going eight-times platinum in the U.S., and turning the previously unknown Gotye into a star.

amazon.com

$1.29

LISTEN NOW

Sometimes relationships fall apart all at once, but oftentimes they crumble in slow motion. A missed phone call here, a late night out with no explanation there. This kind of disintegration is the subject of Whitney's melancholic "Giving Up."

A departure from the sunnier sound of their debut album, "Giving Up" still exists in the same country-soul-indie rock universe, with twangy guitars, dusty piano, and singer Julien Ehrlich's signature reedy tenor.

amazon.com

$1.29

LISTEN NOW

In a different world, "EARFQUAKE" would have been one of 2019's inescapable pop smashes. Tyler, the Creator originally wrote it to give to Justin Bieber, later offering it to Rihanna, before ultimately claiming it for himself. It's hard to picture the song with anyone else on lead vocals. When he pleads, "Don't leave, it's my fault," the desperation is palpable.

amazon.com

$1.29

LISTEN NOW

Some sad love songs are grand and sweeping, but Billie Eilish's "when the party's over" cuts in the complete other direction. With hundreds of layers of vocal harmonies and Eilish's trademark hushed tones, the song feels like it's being sung into your ear from two inches away.

There's an almost religious quality to the lead melody and how it's accented by the harmonies, making "when the party's over" into a vigil for a relationship stuck in the liminal space between friends and lovers.

amazon.com

$1.29

LISTEN NOW

This song brings us into the push-pull of a dysfunctional relationship, one that frequently gets right up to the breaking point without ever crossing that final threshold.

If "Ex-Factor" sounds eerily familiar to younger listeners, it's because Drake sampled it for his huge 2018 hit, "Nice For What."

amazon.com

$1.29

LISTEN NOW

Kacey Musgraves has won acclaim–and many Grammys–for her ability to blend the clever metaphors of old school country songwriting with the humor and edge of a modern millennial. "Space Cowboy" exemplifies both qualities, as Musgraves bids farewell to a partner whose eyes never stopped wandering.

"After the gold rush, there ain't no reason to stay / Shoulda learned from the movies that good guys don't run away," she sings with a weary sigh.

amazon.com

$1.29

LISTEN NOW

Personal baggage can look like many things, and in the case of Haley Heynderickx's "The Bug Collector" it takes the form of centipedes, millipedes, and praying mantises invading a couple's happy homestead.

Heynderickx plays the role of the partner desperately trying to keep the critters in check, but while she occasionally sounds weary, "The Bug Collector" has a core empathy that's reassuring. Pest control is easier with a pal.

amazon.com

$0.99

LISTEN NOW

Minneapolis trio Thank You, I'm Sorry write the kind of earnest, tender love songs that would end up in the climactic scene of an indie rom-com. "Bees?" was originally released as an acoustic track on their project The Malta House, but appears beefed up with drums and amps as part of I'm Glad We're Friends.

"Spent about three hours today / Thinking about how it'd feel /To still be wrapped up in your sheets / The way I was last week / Are you aware of the appeal?" lead singer Colleen Dow poses to the object of their affection.

amazon.com

$1.29

LISTEN NOW

Towards the latter part of his career, Mac Miller moved beyond traditional hip-hop and began penning poignant love songs that showcased his gift for evocative lyrics and melody. "ROS" was one of his sweetest and most candid tracks. It was a more commercially-friendly update on his jazz persona Larry Lovestein, where Miller reflected on his longtime relationship with Nomi Leasure.

"You got your stained glass iris, diamond behind your eyelids / Autopilot fly, my heart skips a beat like a scratched CD," he raps.

amazon.com

$1.29

LISTEN NOW

Even when all the signs are apparent, it can be hard to convince yourself to leave a bad situation once and for all. That's the subject of Syd's "Insecurities," on which she makes it very clear that while she should "be with somebody else," she's sticking around due to her own issues.

"You can thank my insecurities / For keeping me around you babe / I pack my bags but never leave / 'Cause it’s so hard to walk away," she admits.

amazon.com

$1.29

LISTEN NOW

In the video for Juice WRLD's "Robbery," the young rapper crashes an ex's wedding, liquor bottle in hand, face full of regret. It's hard to think of a better visual representation of the single, which takes the idea of "stealing" someone's heart to its logical endpoint.

Even through a layer of autotune, Juice makes his pain known, slurring his words to imitate the kind of drunken stupor that he depicts in the clip.

amazon.com

$1.29

LISTEN NOW

Those of us who struggle with doomsday thinking when it comes to relationships will recognize the emotion at the core of Niia's sultry "Hurt You First." Even when things are going well, it's hard not to fixate on the seemingly inevitable turn for the worse, and for some that ends at a place of, "You can't leave me if I leave you."

"It came from a personal place when I realized it's hard for me to just let things play out," Niia told The Fader.
Especially when it feels too good to be true. I need to control it even if that means messing it up."

amazon.com

$1.29

LISTEN NOW

The video for Shura's "What's It Gonna Be?" is a parody of high school romantic comedies, which is fitting since the song itself has the earnest vulnerability of first-time love. Shura's songs are as catchy as any radio hit, but her music deals with the gray areas of romance, not just ecstasy and sorrow.

"I don't wanna give you up / I don't wanna let you love somebody else but me / So what's it gonna be?" she asks.

amazon.com

$1.29

LISTEN NOW

From "If Only" to "Johnny, It's the Last Time," New York singer Raveena has a real gift for portraying relationships not in an idealized state, but in the messy form that they often take. "Still Dreaming," from her 2019 record Lucid, is another strong entry.

amazon.com

$1.29

LISTEN NOW

Though his career was tragically cut short by an overdose, Lil Peep built a devoted following by writing about love the way it feels as a teenager: always life or death. One of his best tracks was "walk away as the door slams," an in-the-moment narration of a heated argument that features one of Peep's most irresistible hooks.

And if the original isn't enough of a tearjerker, an acoustic version that appeared in the Lil Peep documentary Everybody's Everything applies the song's devastating simplicity to its instrumental.

amazon.com

$1.29

LISTEN NOW

A perceptive partner can always tell when distance is growing in a relationship. That's the subject of Kehlani's "You Should Be Here," which is both a glossy pop anthem and an assertive declaration. Taken from her 2015 mixtape of the same name, the song helped establish Kehlani as an unfiltered R&B star, the kind who has no problem with vulnerability.

"Head on your chest, babe, but your heart is so quiet / We use to talk all night long, now we laying in silence," she sings.

amazon.com

$1.29

LISTEN NOW

Some relationships are capable of shapeshifting from platonic friends to romantic partners and back again, but others just aren't that malleable. On "Thanks 4 Nothing," Nilüfer Yanya confronts a breakup that she knows is really the end of the road. "I don't want to make things better," she croons, a hint of exasperation slipping into her honeyed alto.

For those who want a version that's more suited to crying in the club, check out the Jazzi Bobbi remix.

amazon.com

$0.99

LISTEN NOW

The late Roy Hargrove was one of the key figures in the jazz scene of the late 20th and early 21st centuries, playing with Erykah Badu, Bobby Watson, and D'Angelo, while winning two Grammys of his own.

Great instrumentalists can make their horn as expressive as a human voice, and that's exactly what Hargrove did on "I Fall In Love Too Easily," which opens with long, elegiac trumpet swells, but before long he's reeling off a nimble-fingered solo. Structurally, the song mimics the cycle of heartbreak and healing without a single lyric about love or loss.

amazon.com

$1.29

LISTEN NOW

HAIM has drawn Fleetwood Mac comparisons since the band's early days, and while the Haim sisters' sound has moved in many different directions over the years, both bands share an ability to convey raw emotions on top of beats that make you nod your head and snap your fingers. One recent highlight is "Don't Wanna," which pairs a groovy staircase bass line with lyrics about a difficult open relationship neither party can walk away from.

amazon.com

$1.29

LISTEN NOW

Mainstream pop music sure seems to be getting sadder year by year, and one of the avatars of that shift is Joji, an internet personality-turned-heartbroken heartthrob with a huge fanbase. His singing and songwriting have improved with each subsequent release, and "Run" is his strongest effort yet.

"I know you're not in love like you used to be / Guess I'm not the one, like you used to thin," he intones in a breathy falsetto.

amazon.com

$1.29

LISTEN NOW

Birds of a feather may flock together, but that doesn't mean they should stay together. Inventive singer-songwriter Regina Spektor explores this metaphor on her track "Two Birds."

As with much of Spektor's best music, the song's drama is underscored through creative instrumentation, pulse-pounding drums, percussive piano, as well as burbling horns.

amazon.com

$1.29

LISTEN NOW

Post-relationship heartache is one thing, but the peculiar feeling of learning a crush is actually taken, can also be destabilizing. Alex Izenberg, whose debut album Harlequin is a modern update on the '70s piano pop tradition, explores the topic on his gorgeous, eerie "Grace."

"The darkness has taken over me / Once I'd seen her engagement ring," Izenberg admits.

amazon.com

$0.89

LISTEN NOW

Not all sad love songs are depressing. Some, like Bilal's "Think It Over," capture the bittersweet feeling of fond memories, as well as the nervous optimism of hoping that a spark will be rekindled. Bright guitar and bass from Mike Severson and Thundercat create a warm nostalgic haze, but Bilal's lyrics are frank and direct.

"I feel like you're flying and I'm weighing you down / You should be free to be / Go for now / Maybe the second time around will be sweeter," he sings.

amazon.com

$1.29

LISTEN NOW

Being someone's late-night hookup text recipient might be exhilarating for a while, but eventually you start to wonder why you're only getting messages from them in the wee hours of the morning. Boogie and Snoh Aalegra explore that topic on "Time," a moving song that captures both sides of an asymmetrical dynamic.

"You tell me, 'Come over,' but not when I’m so faded, can I come when I'm sober?" Boogie sings.

amazon.com

$1.29

LISTEN NOW

A Romeo & Juliet update for the Chicago rap set, Chance the Rapper and Noname's "Lost" is about a relationship that's bringing comfort and calamity in equal measure. Over a moody Willie Hutch sample, these two gifted MCs wax about the overlap between love and addiction.

amazon.com

$0.99

LISTEN NOW

Sometimes relationship trouble takes the form of a single thought that lodges itself in the front of your mind and won't budge. Caribou's "Can't Do Without You" replicates that feeling as well as any song ever has, as the titular phrase makes up the song's only lyrics.

Caribou's Dan Snaith stacks synth line after synth line, creating the sonic texture equivalent of finding a perfectly broken in corduroy jacket at your favorite thrift store.

amazon.com

$1.29

LISTEN NOW

The rap song equivalent to a typo-riddled 3 a.m. text to an ex, Drake's "Marvin's Room" captures the superstar at his loneliest. The morose beat is so muffled it sounds like it's coming from a car parked outside, drawing all attention to the lead vocal melody.

Drake, meanwhile, is bleary-eyed and scrolling through his contacts list for the sixth time, looking for someone to save him from himself.

amazon.com

$0.99

Shop Now

Former Chicago band, The Walters, developed a strong cult following in the midwest with their charming, offbeat blend of '50s crooning and contemporary indie rock. Many of their tracks are nostalgic, looking back at past relationships, most notably 2016's "Goodbye Baby." Singer Luke Olson's voice is restrained, but suitably wistful, buoyed by his bandmates' doo-woping in the background.

amazon.com

$1.29

LISTEN NOW

Isaiah Rashad and Syd's "Silkk da Shocka" has the tempo and instrumentation of a rap ballad, and the lyrics themselves are sweet and caring. They play partners in a loving, albeit chaotic relationship, finding in each other an enabler, a co-conspirator, and an anchor for when life feels adrift.

"I am the sky to your star / I am the end of your month / You are the start of my day / You brought the smile from my face," the pair sing together.

amazon.com

$1.29

LISTEN NOW

FKA Twigs is known for so many things, like her elegant, futuristic production, and her otherworldly dancing ability, that sometimes the pure beauty of her voice goes under appreciated. That's not the case on "cellophane," a bare bones ballad about heartbreak on which Twigs stretches the limits of her voice. At times, her falsetto is so delicate that it's reminiscent of ice cracking, perfect for this gutting track that looks back at how a love story ended in tragedy.

"Didn't I do it for you? / Why don’t I do it for you?" she asks, the simple question conveying the pain of a lifetime worth of rejection.