55 Saddest Love Songs of All Time, If You're in Need of a Cathartic Cry (2024)

Taylor Swift has mined the details of her own romantic life to great success, but onLover's"Death by aThousand Cuts" she switchedher approach, drawing inspiration from the Netflix rom-comSomeone 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.

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 LoveYou," which appeared onThe Bodyguardsoundtrack, is one of the 20th century's defining ballads.Houston kept the methodical pacing ofParton'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 whereHouston hits that sky-scraping note on the final hook, always feels stirring.

Bonnie Raitt's 1991 heartbreaker "I Can't Make You LoveMe" 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.

Carole King's landmark 1971 albumTapestryis filled withgorgeous, 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.

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 ofLizzo's music explores her own sense of self-worth and independence, but on "Cuz I LoveYou" 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.

Rihanna's 2016 opusANTIsmartly 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 toYou," a moving piano song about a relationship crumbling in slow motionthat 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.

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 YouAnymore" 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.

Sam Smith has written plenty of songs about the bluer side of romance, but their hit single "Stay With Me" goes to adifferent 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.

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

Johnny Cash originally penned "Give My Love toRose" back in 1957, but it proved to be such a staple of his catalog that he rerecorded it multiple times, including for his 2002 recordAmericanIV: 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.

There are approximately 1 million covers ofBon Iver's "Skinny Love," but none of them hit your gut quite like the original (Birdy's piano-powered takecomes 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 youshouldbe 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.

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 onBeyoncéandLemonade,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.

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.

Few A-listers are as good at lost love ballads asBruno Mars, who has topped charts and made eyes water with songs like "Talking to theMoon,""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.