Best Breakup Albums: 20 Essential Records To Mend A Broken Heart

19: Rod Stewart: ‘Every Picture Tells A Story’ (1971)

From its opening title track, Every Picture Tells A Story sets the mind travelling to the far corners of the world – Paris, Rome, Beijing – garnering vital life experience along the way. Lending his iconic rasp to Bob Dylan’s Tomorrow Is A Long Time, Stewart sings of a man unravelling without the girl he loves around. Listening to Dylan’s poetic lyrics about loneliness, delivered in Stewart’s sage-like voice, is perfect for remembering the one who caused you to feel so alone, while also encouraging you to search for that the silver lining. Perhaps the album’s best-known song, Maggie May truly secures Every Picture Tells A Story as one of the best breakup albums of all time: stinging lyrics such as “The morning sun, when it’s in your face/Really shows your age” and “All you did was wreck my bed/And in the morning, kick me in the head” capture disillusionment with not only a partner, but also love as a whole – and yet you can’t help but try to recapture it all over again.

Must hear: Maggie May

18: Carly Simon: ‘No Secrets’ (1972)

Carly Simon created one of the greatest singer-songwriter albums of all time in No Secrets. Deeply personal and incessantly groovy, the record tells tales of falling in love (The Right Thing To Do), describes the uncertainty of a relationship where everything is on the table (No Secrets) and provides a cathartic kiss-off to a narcissistic ex-lover (You’re So Vain). There is nothing more therapeutic than performing You’re So Vain in the mirror, hairbrush-microphone in hand, surrounded by the imagined audience of every single self-obsessed ex you’ve ever had. From its opening whisper, “Son of a gun,” to the sneering put-down “I’ll bet you think this song is about you/Don’t you? Don’t you? Don’t you”, Simon’s song has been a pop culture touchstone for generations, epitomising the breakup song.

Must hear: You’re So Vain

17: Willie Nelson: ‘Phases And Stages’ (1974)

When you think of concept albums, country music isn’t often a genre that comes to mind. Yet, in 1974, Willie Nelson wrote Phases And Stages, one of the best breakup albums of all time. The first half tells the story from the perspective of a woman who’s leaving a relationship, while the second moves to the point of view of the man who’s being left; the central theme is that everything in life happens in phases. The woman ultimately starts to fall in love again, but her ex is still on her mind; the man escapes into a “Bloody Mary morning”, or the smokescreen of cowboy machismo. The most moving song on the album is I Still Can’t Believe You’re Gone: the emptiness described in its lyrics (“I tried to put my thoughts in a song/And all I can hear myself singin’ is/‘I still can’t believe you’re gone’”) is echoed in Nelson’s voice, which is as worn and scraggly as the Texas plains.

Must hear: I Still Can’t Believe You’re Gone

16: Enya: ‘Watermark’ (1988)

Picture yourself on a rocky cliff on the coast of Ireland, with the mist in your face as you think about your unrequited love. That is where Enya’s 1988 album, Watermark, takes you. The Old World-meets-New World sound that she has mastered will envelop you, body and soul, as it whisks you away from heartache and into a daydream. Sometimes when a relationship fails, you don’t want to hear someone say that it’s all going to be OK – you just want to ruminate. And Enya’s oceanic ambience is perfect for that. Inspired by a poem written by her long-time collaborator Roma Ryan (“In your heart is the island/Where memories wash on the shore/Love is an ocean”), Watermark’s opening title track was eventually shaped into an instrumental (the lyrics were later printed in the 2002 reissue of the album), and it continues to endure among the best Enya songs, capturing the fluidity of emotions experienced during heartbreak.

Must hear: Watermark

15: Stevie Nicks: ‘Bella Donna’ (1981)

“Come in out of the darkness” Stevie Nicks sings, beckoning listeners into her fairy-tale land of moons, stars, glitter, lace and doves. With songs that both enchant and haunt, Bella Donna encapsulates the extremes of falling in love – and then falling out of it. From demanding Heartbreaker Tom Petty to Stop Draggin’ My Heart Around, to falling head-over-heels in love with Eagle Don Henley in Leather And Lace, Nicks lays her own heart on the line. Her undeniable experience in the realm of romantic bust-ups is what gives the best Stevie Nicks songs such clarity, and it is surely no accident that Bella Donna’s title, which translates as “beautiful woman” in English, is also the nickname for an extremely poisonous plant – a perfect metaphor for love that fuels one of the best breakup albums of the 80s.

Must hear: Stop Draggin’ My Heart Around

14: Frank Sinatra: ‘In The Wee Small Hours’ (1955)

In The Wee Small Hours’ album cover a depicts Frank Sinatra alone under a street lamp, a cigarette burning in his hand – a hint at the contemplative nature of the album as a whole. The song Deep In A Dream finds him unfolding a beautifully heartbreaking vignette full of vivid imagery: as he falls asleep in his chair, the plume of smoke from his cigarette fashions a stairway for his past lover to descend into his dreams, where they can be together again. Unexpectedly, that same cigarette burns him awake – a perfect metaphor for the blistering pain of a breaking heart. A number of Sinatra albums could take their place among the best breakup albums of all time, but, exploring how life without love lacks magic, In The Wee Small Hours clinches it. From Nelson Riddle’s weepy string arrangements to Ol’ Blue Eyes’ sombre crooning, it encapsulates the miserable experience of breaking up.

Must hear: Deep In A Dream

13: Paramore: ‘Riot!’ (2007)

Filled with catchy hooks and biting lyrics about infidelity, the experience of heartbreak and, more importantly, overcoming it all, Paramore’s second album, Riot!, immediately established itself as one of the best breakup albums of the 21st century. The album’s central focus is on triumphing over adversity, but it is scattered with reminders that the bad stuff has to come before the good. One of the best female singers of her generation, Hayley Williams’ voice is packed with a power that makes it not only perfect listening for when you’re feeling weak, but also cathartic to sing along with (case in point: Misery Business). The album’s final single, That’s What You Get, seamlessly captures the waves of regret that come after the necessary end of a co-dependent relationship, especially in the lyrics “I wonder, how am I supposed to feel when you’re not here?/’Cause I burned every bridge I ever built when you were here”. Running punk attitude through an ironic filter, Riot! features many of the best Paramore songs, and it provides a throughline for the modern era’s approach to breakup music, as exemplified by Hayley Williams’ songwriting credit on Good 4 U, the runaway Olivia Rodrigo hit that became one of the best songs of 2021.

Must hear: That’s What You Get

12: Otis Redding: ‘Dock Of The Bay’ (1968)

Otis Redding’s voice can at once stir and soothe a broken heart. The posthumous Dock Of The Bay album, released after the soul music world suffered its own heartbreak over the singer’s tragic death, featured his usual mix of rhythm’n’blues, Memphis grooves and crossover rock-soul. (Sittin’ On) The Dock Of The Bay alone is enough to capture the desperation that comes with the worst breakups (“’Cause I’ve had nothin’ to live for/And look like nothing’s gonna come my way”), but, as with many of the best Otis Redding songs[https://www.thisisdig.com/feature/best-otis-redding-songs/], the overall vibe is calming, offering reassurance that someone else can feel the same way. Meanwhile, the lyrics of I Love You More Than Words Can Say lay it out clear enough: “You’ve got me in your hand/Why can’t you understand/I love you, baby/Far more than words can say?” The way Redding sings, stretching and punctuating his words like a saxophonist plays his horn, takes him from pleading to full-blown possession. Soul music is always a salve, and it doesn’t get much better than this.

Must hear: I Love You More Than Words Can Say

11: Joy Division: ‘Closer’ (1980)

Opening with Ian Curtis’ haunting croon – “This is the way, step inside” – Closer, Joy Division’s second and final album, offers an invitation into the depths of the Manchester icons’ sonic nightmare. The album is a pillar of post-punk music, with Ian Curtis’ lyrics providing an almost unbearable melancholy against its ascetic musical backing. The results perfectly channel feelings of romantic catastrophe, as themes of betrayal, loneliness and change weave around images of asylums and the abyss of oblivion. With hindsight, the knowledge of Curtis’ tragic death only serves to make the album that much more affecting. “Now that I’ve realised how it’s all gone wrong/Gotta find some therapy, this treatment takes too long,” he sings on Twenty Four Hours, underscoring why Closer makes for a unique listen among the best breakup albums.

Must hear: Twenty Four Hours

10: Eagles: ‘One Of These Nights’ (1975)

Original vinyl pressings of Eagles’ 1975 album, One Of These Nights, immediately made a case for its inclusion among the best breakup albums of all time. With side one featuring an etching that reads “Don’t worry –”, and side two continuing, “– Nothing will be O.K.!”, the album itself presents a sombre portrait of the aftermath of a breakup. One of the best Eagles songs of all time, Lyin’ Eyes tells the tale of a woman cheating on her “rich old” husband with “a boy she knew in school”, Glenn Frey’s melancholy vocals cutting straight to the heart as he sings, “Ain’t it funny how your new life didn’t change things?” In Take It To The Limit, the group provide the perfect song for picking yourself up again: with a forlorn falsetto, Randy Meisner sings of life on the road, where relationships never really work out. Amid climactic orchestration and harmonies, he hits impressively high notes at the end, repeating, “Take it to the limit, one more time” – a reminder to persevere, even when we get knocked down. With Eagles’ Southern-soaked harmonies, slick guitar solos and Don Henley’s heartbeat-like timekeeping, One Of These Nights provides the perfect post-breakup escapism.

Must hear: Lyin’ Eyes

9: Carole King: ‘Tapestry’ (1971)

One of the best breakup albums of the 70s, Carole King’s Tapestry is mélange of soft rock and jazz that weaves together the highs and lows of life in order to create a deeply personal album. So Far Away deliberates on the strains of a long-distance relationship (both physically and emotionally) while It’s Too Late discusses how, sometimes, relationships just don’t work (“One of us is changin’, or maybe we just stopped tryin’”). King’s jazz leanings allow her to not only express emotion lyrically, but also musically. The piano becomes an extension of her body, with syncopation creating tension in the underlying melody while the free-form horn and guitar solos organically express the things that go unsaid – the musical equivalent of a flickering flame that ultimately burns out. Avoiding anger or bitterness, it’s a breakup song that acknowledges the pain but also recognises that it’s important to remain optimistic. In You’ve Got A Friend, meanwhile, Carole King reminds us that, should love go wrong, she will always be there for us, in the form of Tapestry.

Must hear: It’s Too Late

8: The Cure: ‘Disintegration’ (1989)

In 1989, The Cure perfected their grand, moody aesthetic with Disintegration, creating a soundtrack for broken hearts the world over. The record’s synth-leaden soundscapes provide a sort of comfort, inviting anyone dissatisfied with life and love to find shelter in its walls of sound. Pictures Of You – all seven and a half minutes of it – is the ultimate song for dejected lovers to get teary-eyed over while scrolling through old photos of their ex. Lines such as “There was nothing in the world that I ever wanted more/Than to feel you deep in my heart” cuts deep to that very organ, and are probably still scribbled in the notebooks of every good goth kid to this day.

Must hear: Pictures Of You

7: Tom Petty: ‘Wildflowers’ (1994)

Written during a particularly tumultuous time in his life, Wildflowers was Tom Petty’s escape from it all. Though dealing with a split from his wife of over two decades, creativity seemed to pour from him, with some songs making it on to the album with few changes to the stream-of-consciousness form they tumbled out in. The ultimate “no hard feelings” tune, Wildflowers’ title track offers well-wishes to an ex-lover, hoping they will be happy, free, and loved – but by someone else. Elsewhere, You Don’t Know How It Feels offers solid advice for moving on: “Let me get to the point, let’s roll another joint/And turn the radio loud, I’m too alone to be proud.” An example of how the best breakup albums can deftly untangle complexities of the heart, the record uses multiple musical styles to work through the bundle of emotions that follow the dissolution of a relationship. At the centre is Only A Broken Heart, sung gently, with minimal instrumentation that highlight the comforting lyrics: “Don’t be afraid anymore/It’s only a broken heart.”

Must hear: Only A Broken Heart

6: Bob Dylan: ‘Blood On The Tracks’ (1974)

Always trying to slip out of any attempts to define him, Bob Dylan bared his soul on Blood On The Tracks, written in response to his split from his first wife, Sara. From the melancholic Simple Twist Of Fate to the scathing Idiot Wind, Dylan envelops the listener in his grief and fury, with the likes of Simple Twist Of Fate telling the story of a man idly wandering while romanticising a relationship that could have been. From abstract narratives to standard blues structures and evocative imagery (You’re A Big Girl Now’s “I’m going out of my mind/With a pain that stops and starts/Like a corkscrew to my heart/Ever since we’ve been apart”), Blood On The Tracks features a variety of styles of breakup song, each one so painfully honest it’s as if Dylan’s own veins form the vinyl’s grooves, the needle cutting as it turns.

Must hear: Simple Twist Of Fate

5: Alanis Morissette: ‘Jagged Little Pill’ (1995)

An incredibly honest album on which Alanis Morissette reveals her deepest secrets, Jagged Little Pill is full of sarcasm, eye-rolls and angst – not least on You Oughta Know, which finds her choking back tears to sing “I want you to know, that I’m happy for you”. Moved by anger, Morissette interrupts her ex’s date to remind him of all his injustices – a moment that many romantic comedies have since enjoyed dramatising. One of the best breakup albums of the 90s, Jagged Little Pill also includes many of the best Alanis Morissette songs of all time, among them the mega hit Ironic, and it is brought to a close by the hidden track Your House. A melancholy a cappella tune, the song finds Morissette breaking into her ex’s house in order to feel close to him again. “Went down to the den/Found your CDs/And I played your Joni”, she sings – which is a fitting way for us to introduce…

Must hear: You Oughta Know

4: Dolly Parton: ‘Jolene’ (1974)

Written around the time of her professional breakup with Porter Wagoner, Dolly Parton’s 1974 album, Jolene, features two of the most heartbreaking songs of all time. Country music, with its roots in the blues and folk traditions, captures the deepest of emotions, and in Jolene’s title track, Parton created a brutally realistic song about everyone’s worst fear: being left for someone else. Elsewhere, I Will Always Love You resonates profoundly – whether you’re the one leaving, or the one being left – with Parton speaking the perfect departing words: “And I wish you joy and happiness/But above all of this/I wish you love/And I will always love you”. Walking the line between heartbreak and happiness, and distilling a relationship into a “bittersweet memory”, Jolene hit No.6 on the US Hot Country Albums chart, but stands as one of the best breakup albums in any genre. With her inexplicably angelic voice, Parton guides us through emotions that are often too difficult to put into words.

Must hear: Jolene

3: Joni Mitchell: ‘Blue’ (1971)

Joni Mitchell’s landmark album Blue reflects on her experiences of loss and metamorphosis through song, and sees her singing about her deepest sources of regret, from putting her newborn daughter up for adoption, to feelings of homesickness and failed relationships. Like Elizabeth Gilbert’s book Eat, Pray, Love in album form, Blue finds Mitchell examining her travels as a way of getting back in touch with herself. In California she sings of wanting to get back to The Golden State after experiencing life in Paris, where she felt isolated; on a Greek island, where a man gave her back her smile; and Spain, where she got a suntan. The album ends with the moody The Last Time I Saw Richard, in which she sits alone in a dark café. Though it’s a gloomy listen, it is one of the best Joni Mitchell songs and it offers a glimmer of optimism as Mitchell sings, “Only a dark cocoon before I get my gorgeous wings/And fly away.” One of the best breakup albums of all time, Blue tells us that the struggles of heartbreak are necessary in order to appreciate the beauties of freedom.

Must hear: A Case Of You

2: Aretha Franklin: ‘Spirit In The Dark’ (1970)

Spirit In The Dark’s opening track, Don’t Play That Song, expresses the power music can have when you’re falling in – and, ultimately – falling out of love, examining how a song that once brought someone so much joy now causes feelings of anger at the realisation that her partner lied when he said he loved her. With an artful interpretation of BB King’s bluesy The Thrill Is Gone, Aretha Franklin laments how life seems so much more dull without her lover in the picture, while Pullin’ drags listeners towards feeling better about moving on and Oh No Not My Baby encapsulates feelings of denial that can accompany the finality of breaking up. One of the most influential Black musicians of all time, Franklin had the unique and cathartic ability to pierce your heart with her vocals, hurt you with her lyrics and make her piano shake you to the bone. She elicits hidden emotions and makes you feel the ache until you move on, making Spirit In The Dark the perfect breakup album.

Must hear: Don’t Play That Song

1: Fleetwood Mac: ‘Rumours’ (1977)

Recorded while Fleetwood Mac’s personal relationships were on the rocks, Rumours tops our list of the best breakup albums. Epitomising the very concept of the breakup record, it was written while Stevie Nicks and Lindsey Buckingham were in the middle of splitting-up, Christine and John McVie were divorcing, and Mick Fleetwood was in the process of leaving his wife, rock muse Jenny Boyd. As such, Rumours’ boasts many of the best Fleetwood Mac songs – all in conversation with each other. Stevie Nicks’ ethereal Dreams takes a philosophical approach, hinting at the psychological guilt of Edgar Allan Poe’s A Tell-Tale Heart in the line “A heartbeat drives you mad”, and creating a mantra to quell her own broken heart: “Thunder only happens when it’s raining/Players only love you when they’re playing”. Lindsey Buckingham’s furious Go Your Own Way, meanwhile, lays it all out with the line “Packing up, shaking up’s all you wanna do” – an immortal kiss-off from one of the best breakup songs ever written. It’s a pleading, stream-of-consciousness song that says, “If I could, baby, I’d give you my world,” while also asserting that he’s done with her. Shouting at each other in harmony offers catharsis for both the singers and listeners, while Buckingham’s scathing guitar solo sees him further playing out his frustrations. Yet while their personal lives were in disarray, Fleetwood Mac knew that one thing remained: the core value of the band would “never break the chain”. Making beauty out of pain has always been the role of the artist, and, in the case of Fleetwood Mac, they transmuted all their heartache into Rumours.

Must hear: Dreams

Still feeling blue? Check out our best breakup songs of all time.

Original article: 4 February 2021

Updated: 19 January 2023