1. Fleetwood Mac, Rumours
The ultimate breakup album, and the rare collection of songs to offer both sides of the story, since the record largely documents the dissolution of Lindsey Buckingham and Stevie Nicks’ long-term relationship with each other. As an added bonus, Christine McVie’s songs are about the aftermath of her split from her husband and bandmate John McVie. Every song on the record deals with some aspect of heartbreak, but Buckingham’s “Go Your Own Way” stands out as possibly the most passive-aggressive rock anthem of all time.
2. Fiona Apple, The Idler Wheel…
Fiona Apple’s entire body of work is perfect breakup music; any of her four albums are an excellent soundtrack for wallowing in pain. The Idler Wheel…, her most recent, is the most raw, and extra devastating in the way she places most of the blame on herself. “How can I ask anyone to love me when all I do is beg to be left alone?” she howls on one of the album’s best cuts. It’s harrowing stuff.
3. Kanye West, 808s and Heartbreak
Kanye West’s most experimental album is also his most nakedly emotional, with a hundred shades of icy AutoTune barely masking his anger, sorrow, and self-pity.
4. Blur, 13
13 was a creative departure for Blur, a band better known for scathing parodies of modern British life than for depressive, confessional ballads. Damon Albarn went all in with this record, dealing with the aftermath of his relationship with Elastica singer Justine Frischmann with a set of brutally cathartic and heartbreaking tunes about recognizing that something central to your life is now completely gone.
5. Beck, Sea Change
Beck was so distraught after the end of his long-term relationship with stylist Leigh Limon that he made a hard stylistic turn away from the bright, funky music of Odelay and Midnite Vultures to create this collection of slow, almost unbearably sad meditations on loss and loneliness.
6. Patsy Cline, Showcase
Patsy Cline’s second album is a classic from top to bottom, but if you’ve just been dumped, you’re probably only going to end up playing the timeless, extraordinarily melancholy hits “Crazy” and “I Fall to Pieces” on an endless loop.
7. Joni Mitchell, Blue
Joni Mitchell’s fourth album is the perfect relationship post-mortem record, looking back on the good and the bad times with a mix of bittersweet fondness and lingering grief.
8. Elliott Smith, Either/Or
Elliott Smith’s entire body of work is rather depressive, but Either/Or is the album that best captures the self-loathing and wounded pride of someone who can’t quite get over a broken relationship.
9. Adele, 21
Adele’s second album is a blockbuster of undiluted post-breakup trauma, from the righteous indignation of “Rolling in the Deep” to the all-out despair of “Someone Like You” and everything in between.
10. Robyn, Body Talk
Robyn has a long history of writing perfect, emotionally gutting breakup songs, but this collection of songs is her creative peak, with “Dancing on My Own,” “Indestructible,” and “Call Your Girlfriend” forming the ultimate trifecta of dance-away-the-tears anthems.
11. Mary J. Blige, Share My World
Mary J. Blige’s third album is a tour de force of heart-crushing R&B, packed with intense songs about living with and without love. “Not Gon’ Cry” is the masterstroke, a clear-eyed ballad about finding the strength to let go of someone who is all wrong for you.
12. Taylor Swift, Speak Now
Taylor Swift has made a career out of penning bitter breakup tunes, so really, any of her albums could do the trick. Speak Now finds the ideal balance between pop hooks and genuine country-rock melancholy, to the point that you can easily listen to a track like “Dear John” without thinking too much about the fact that it’s about John Mayer.
13. The Mountain Goats, Get Lonely
John Darnielle, one of the great modern poets of misery, focuses on the dissolution of a relationship over the course of this record, resulting in some of the most excruciatingly sad music of his career.
14. Björk, Homogenic
Björk’s artistic masterpiece is also a phenomenal breakup album, with the first half of the set focused mainly on characters searching for freedom, while the second half is full of brutally frank lyrics about moving on from a failed relationship. “5 Years” is particularly powerful, with the Icelandic singer chastising her ex as a coward who “can’t handle love.”
15. Otis Redding, Lonely & Blue
This compilation is billed as a set of Otis Redding’s “deepest soul,” but it’s more accurately described as his most heartbreaking ballads. It is almost impossible to find music that captures the feeling of lovelorn desperation as well as “These Arms of Mine” and “I Love You More Than Words Can Say.”
16. Carole King, Tapestry
Carole King’s blockbuster album covers a range of emotions, but it’s most memorable moments fixate on fading love. “It’s Too Late” is one of the all-time best breakup songs: a perfect evocation of the moment you know that while you love someone, you’re not in love with them anymore.
17. Bat for Lashes, Two Suns
Breakups have a way of blowing our emotions way out of proportion, and Natasha Khan runs with that all through her second album as Bat for Lashes, giving every song an epic, cinematic scale. The most devastating track, “Siren Song,” is sung from the perspective of a woman struggling with guilt as she strings along a man she’s about to leave heartbroken. “My name is Pearl and I love you the best way I know how,” she sings before admitting a few moments later, “but I’m evil, I’m evil.”
18. Wilco, Yankee Hotel Foxtrot
Jeff Tweedy has written dozens of songs about romantic disaster despite being married for many years, but he hit his peak with this record, which ping-pongs between reticence (“I Am Trying to Break Your Heart”) and emphatic commitment (“I’m the Man Who Loves You”). There are at least a dozen couplets on this record that will cut your heart in two, but the defining moment of the record comes when Tweedy creaks the line, “Oh, distance has no way of making love understandable” on “Radio Cure.”
19. Kelly Clarkson, Breakaway
“Since U Been Gone” may be the “I’m moving on, and good riddance!” anthem of the entire ’00s, but it’s not the only amazing breakup song on Breakaway. The title track and “Walk Away” nail a similar sentiment, so it’s no surprise that Clarkson has become a hero to jilted lovers everywhere.
20. Sleater-Kinney, The Hot Rock
Sleater-Kinney wrote a lot of emotionally raw breakup songs in the late ’90s, but their 1998 album The Hot Rock is almost exclusively focused on romantic turmoil. The most powerful songs contrast Carrie Brownstein and Corin Tucker’s voices for dramatic effect, with Brownstein’s cool vocals giving voice to rational thoughts while Tucker’s hyper-emotive wail delivers emotional sucker punches like “It’s not real / You don’t need to tell me that it’s NOT REEEEAAAALLLL!”
21. Marvin Gaye, Here, My Dear
This 1978 album was initially a commercial flop, but it’s since become a soul classic thanks to its frank, intensely personal depiction of Gaye’s painful, deeply contentious split from his first wife, Anna Gordy.
22. Bob Dylan, Blood on the Tracks
Bob Dylan has denied that the songs on this bitter, lovesick record are autobiographical, but it’s hard to believe — every word and note sounds very lived-in and true. But even if he’s telling the truth, the effect is all the same.
23. Of Montreal, Paralytic Stalks
Kevin Barnes has spent a lot of time writing incredibly angst-ridden songs about romantic strife, but Paralytic Stalks is the Of Montreal album that goes deepest into the darkest corners of his psyche. This is the record for the phase of the breakup where you absolutely loathe your ex. To get a sense of how far this record goes, one of its most lighthearted tunes has the chorus “I spend my waking hours haunting my own life / I made the one I love cry tonight / and it felt gooooood.” You’ve been warned.
24. Carrie Underwood, Some Hearts
Carrie Underwood’s hugely popular debut covers a lot of emotional ground, but if you’re at the end of your rope with a cheating partner, “Before He Cheats” is your jam. Can you think of a more brutal and specific song about getting revenge on a cheater?
25. Jack White, Blunderbuss
Jack White has been writing kiss-off songs for years, but his solo debut is his most bitter and heartbroken. It can be hard to tell whether he’s mourning the end of his marriage or the breakup of The White Stripes, but there’s no mistaking the bile that fuels tracks like “Sixteen Saltines” and “Hypocritical Kiss.”
26. The Cure, Disintegration
The Cure perfected their brand of gloomy romanticism on this record and gave the world some of the most perfect songs for reflecting on love and loss. It’s depressive, sure, but it’s sung from the perspective of a person who truly believes in love.
27. Sebadoh, Bakesale
Lou Barlow and Jason Loewenstein dwell on romantic catastrophe on every Sebadoh record, but Bakesale is the album where their punk aggression and passive-aggressive lyrical style came together most perfectly. “Rebound,” in particular, is the perfect song for anyone in a manic, promiscuous phase after splitting with a long-term partner.
28. The Weeknd, Trilogy
Abel Tesfaye’s songs are almost exclusively meditations on romantic and sexual angst. Trilogy, a collection of his three acclaimed mixtape albums, makes sulking sound sexy, even when the lyrics basically amount to Tesfaye crying, “LOOK WHAT YOU’VE DONE TO ME!” at his ex.
29. Beach House, Teen Dream
Teen Dream perfectly captures the numb feeling that can come after a particular traumatic breakup. The dark emotions linger, but the dominant sentiment is working through pain to get to a better place. As Victoria Legrand sings on “Walk in the Park,” “In a matter of time / It would slip from my mind / In and out of my life.”
30. Alanis Morrissette, Jagged Little Pill
Alanis Morrissette covers a lot of emotional ground on Jagged Little Pill, and if you sequence the record differently, you can make it a story about someone who falls madly in love, falls waaaaay out of love, and then gets over it. But let’s be real: You need this because “You Oughta Know” is one of the most fierce kiss-off songs ever written.
31. Bon Iver, For Emma, Forever Ago
Justin Vernon’s debut album as Bon Iver is basically an indie-folk legend by now: After a bad breakup, he hid away in a cabin in rural Wisconsin and wrote the perfect album for anyone yearning to basically disappear from the world after getting their heart broken.
32. Liz Phair, Exile in Guyville
Liz Phair’s brilliant debut cycles through many feelings, but the most potent cuts deal with the aftermath of a complicated relationship. Nothing comes easy in Phair’s world, and she never lets herself off the hook. In “Divorce Song,” the album’s most painful song about a split, she admits, “It’s harder to be friends than lovers, and you shouldn’t try to mix the two / Because if you do it and you’re still unhappy, you know that the problem is you.”
33. Death Cab for Cutie, Transatlanticism
Even in the context of Ben Gibbard’s catalog, Transatlanticism stands out as an epic of heartbreak. The title track is particularly powerful, expressing an all-consuming need for someone who seems to drift further away by the moment.
34. Brand New, Deja Entendu
Brand New’s second album is a dark and brooding meditation on how fragile you feel as a teenager, navigating a world that you don’t really understand. Deja Entendu takes the heart-on-your-sleeve spirit of a Smiths album and then strips any hope or whimsy, resulting in a relentlessly depressing but ultimately cathartic set of songs.
35. Frank Sinatra, In the Wee Small Hours
Frank Sinatra is famous for his unflappable cool, but one of his finest albums is a set of jazz vocal tunes that wallows in despair and self-pity. It’s the perfect record for the sad guy drinking a martini by himself at the end of the bar.
36. Tegan and Sara, The Con
The Con sounds upbeat, but Tegan and Sara’s lyrics go to some dark emotional places, and say the sort of things that you might write to someone you’re breaking up with in the middle of the night but then not actually hit send.
37. Mary Wells, The Ultimate Collection
Motown legend Mary Wells had a lovely, slightly weary voice that was ideal for up-tempo tunes with melancholy themes: “What’s Easy for Two Is So Hard for One,” “You Lost the Sweetest Boy,” and, most especially, “The One Who Really Loves You.” This is what you play when you’re almost over the worst of it but can’t quite let it go.
38. Portishead, Dummy
Portishead’s debut album makes self-pity seem totally glamorous and sexy. The album is elegantly depressive from start to finish, but it’s hard to top the moment in “Sour Times” when Beth Gibbons sings “Nobody loves me, it’s true / Not like you do” with a tone that’s as self-loathing as it is seductive.
39. Rilo Kiley, More Adventurous
Jenny Lewis’ characters on More Adventurous can’t stop making bad decisions — falling into bed too soon with the wrong guys, becoming obsessed with married men, and showing up at the ex’s house of nowhere. There are a lot of grim moments, but there’s at least one bright spot: “I Never,” a gorgeous ballad pining for the ideal partner you just haven’t met yet.
40. Ryan Adams, Heartbreaker
Ryan Adams has spent his career mainly writing songs about breaking hearts or being heartbroken, so it makes perfect sense that his most widely loved record would just be called Heartbreaker. It’s a very, very accurate title.
41. The Mynabirds, What We Lose in the Fire We Gain in the Flood
Laura Burhenn’s first album as the singer of the blue-eyed soul band The Mynabirds takes a philosophical approach to the end of a relationship, balancing out a palpable sadness with a clear-eyed fatalism.
42. Beyoncé, B’Day
Even Beyoncé can feel rejected! No one could be more furious about that fact than Beyoncé herself, as she storms through songs directed at the “other woman” and ungrateful lovers with an imperious rage. There are moments of vulnerability too, but the power of this album is in how it makes you feel that you, too, are irreplaceable.
43. Lily Allen, It’s Not Me, It’s You
Lily Allen’s second album is snarky, bitter, and impossibly catchy, with songs that lash out at unacceptable suitors, inadequate boyfriends, and, ultimately, herself.
44. PJ Harvey, Rid of Me
If you’re feeling a little…intense after a messy breakup, PJ Harvey is there for you. Rid of Me has a raw, spontaneous sound, and songs about love, sex, and revenge that turn on a dime from almost uncomfortably intimate to extremely loud and aggressive.
45. Derek and the Dominos, Layla and Other Assorted Love Songs
Eric Clapton’s only album as the frontman of Derek and the Dominos is a lovesick blues rock epic that culminates with “Layla,” a seven-minute classic about his painful, then-unrequited love for his best friend’s wife.
46. Cat Power, The Greatest
Cat Power’s entire discography is a perfect soundtrack for post-breakup sadness, but The Greatest is the one with a balance of raw-nerve emotion and a measure of hope for the future. It’s the record for when you’re emotionally bruised but convinced that you’ll eventually be stronger for it.
47. Pretty much any greatest hits collection by George Jones
George Jones made it his life’s work to perform some of the saddest, most painful tunes about heartbreak in the history of country, or pop music in general. Any George Jones record will do, but aim for one of his many hits compilations.
48. Rachael Yamagata, Happenstance
Rachael Yamagata’s debut may dwell on romantic turmoil and unrequited love, but it’s not a dark or dour record — if anything, she finds a way to let go of lingering pain in songs like “Letter Read” and “Under My Skin.”
49. Dashboard Confessional, The Places You Have Come to Fear the Most
Dashboard Confessional practically sounds like a breakup, with songs that alternate between unnerving quiet and bursts of desperate shouting. The Places You Have Come to Fear the Most is the ideal soundtrack for building a blanket fort of sadness in your bedroom after all the shouting is done.
50. The Magnetic Fields, 69 Love Songs
Just as the title says, it’s 69 love songs. Some of them might not feel right after a breakup, but there are at least 20 or so darkly humorous songs about getting dumped that will do the trick.