Best Break-Up Albums: 25 Records To Heal Broken Hearts

The best break-up albums channel personal pain into universally affecting works of art with an overriding message: you are not alone.

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Spare a thought for those who are alone on Valentine’s Day, contemplating a microwave meal for one. Of course, some people are single by choice, but others have been brutally thrust into a solitary life by a lover’s callous betrayal. As many a musician can attest, however, there’s nothing like being dumped to focus the mind – and the best break-up albums can channel that personal pain into creating universally affecting works of art.

As well as facilitating mental clarity, heartbreak can bring with it self-pity, jealousy, bitterness, anger, and even a desire for revenge. As damaging as those emotions can be, they are all grist to the mill for people of a creative bent. Where would popular music be without the psychological pain and suffering that has both tormented and inspired its creators? If love and life were always trouble-free and blissful, we would not have three of the most potent autobiographical albums birthed by the trauma of love gone bad: Amy Winehouse’s Back To Black, Bob Dylan’s Blood On The Tracks, and Marvin Gaye’s Here, My Dear.

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Those, and other entries in this list of the best break-up albums, show how great artists can find catharsis in confronting the forces that seem intent on destroying their lives and taking their sanity. Of course, not all the albums below were forged in a crucible of pain – some are present because the moods they create and the universal truths they offer can help listeners cope with their own emotional crises. Their overriding message is: you are not alone.

Think we’ve missed one of your best break-up albums? Let us know in the comments section, below.

While you’re reading, listen to our Break-Up Songs playlist here.

25: Robin Thicke: Paula (Star Trak/Interscope, 2014)

Praised by fans for its unflinching honesty, this concept album was the blue-eyed R&B singer’s attempt to offer an apology and woo back his former wife, Paula Patton, after their split. Agonizingly graphic in its detail, Paula isn’t an easy listen but offers a compelling portrait of a heartbroken sinner seeking redemption.
Must hear: “Black Tar Cloud”

24: Julie London: Julie Is Her Name (Liberty, 1955)

For those feeling disconsolate after being betrayed in love, this album won’t make them feel any better. What it will do, however, is assure them that London, an adept torch-song siren, knows what their pain feels like. The album’s pièce de résistance is the opening song, “Cry Me A River”: an anthem for the heartbroken, distinguished by a bitter retort.
Must hear: “Cry Me A River”

23: No Doubt: Tragic Kingdom (Trauma/Interscope, 1995)

This, the eclectic California group’s Grammy-nominated breakthrough album, enjoyed multi-platinum sales and catapulted them firmly into the pop mainstream. But behind its phenomenal global success there lay a tale of hurt, betrayal, and heartbreak. Several songs – in particular, the chart-topping power ballad “Don’t Speak” – documented lead singer Gwen Stefani’s split from the band’s bassist, Tony Kanal, after he called time on their seven-year relationship.
Must hear: “Don’t Speak”

22: Patsy Cline: Showcase (Decca, 1961)

A Virginia-born country singer who conquered the mainstream pop charts in the early 60s, Patsy Cline possessed a beautiful voice whose plangent tone had a natural affinity for communicating heartbreak and sadness. There’s plenty of both on Showcase, her second studio album, recorded two years before she died in a plane crash, aged just 30. Showcase contained some of Cline’s most famous songs, including “I Fall To Pieces” and an indelible version of Willie Nelson’s “Crazy,” the latter a lovelorn hymn of loneliness and rejection that should only be listened to if you have a box of tissues to hand.
Must hear: “Crazy”

21: Lorde: Melodrama (Universal, 2017)

After the austere electro minimalism of her 2013 debut album, Pure Heroine, this New Zealand singer-songwriter used a bigger sonic canvas and more expansive production values for Melodrama. The studio gloss couldn’t mask the hurt expressed in a collection of songs that chronicled Lorde’s feelings about a painful, life-altering break-up with her boyfriend after a three-year relationship.
Must hear: “Hard Feelings”/“Loveless”

20: Taylor Swift: Red (Big Machine, 2012)

There’s nothing like a broken heart to fan the red-hot flames of creativity while prompting serious self-analysis. On this emotional exposé, country-pop siren Taylor Swift wrote about the toxicity of her past relationships. Though on “I Knew You Were Trouble,” “Treacherous,” and “We Are Never Getting Back Together,” Swift doesn’t dilute her sense of anger and bitterness, she shows a more reflective side on the plaintive “Sad Beautiful Tragic.”
Must hear: “Sad Beautiful Tragic”

19: Nas: Life Is Good (Def Jam, 2012)

An MC renowned for his braggadocio and his weaponization of language, Nas revealed his rarely-seen vulnerable side on Life Is Good. This breakup album documented his divorce from singer Kelis, whose wedding dress is draped over the rapper’s lap on its provocative front cover. It wasn’t the emotional damage of separation that seemed to concern him, rather the pain of financial settlement: “I talk about the fact that marriage is expensive,” he confessed in an interview at the time. Even so, Life Is Good is unflinchingly raw and honest in its depiction of love gone wrong.
Must hear: “Bye Baby”

18: Joan Baez: Diamonds & Rust (A&M, 1975)

The patron saint of 60s acoustic folk, Baez recorded this album in Hollywood, opting for a more mainstream jazz-rock sound played by LA’s top session cats. Despite the gleaming studio polish, the collection couldn’t conceal the rawness of the singer’s feelings for a former beau, Bob Dylan, expressed in the memorable title song. She also adds a sardonic twist to the lyrics of her rocked-up cover of Dylan’s “Simple Twist Of Fate” (including an arch impersonation of its author’s idiosyncratic singing style). But it’s her rendition of Jackson Browne’s “Fountain Of Sorrow” that best crystallizes the album’s downcast, elegiac mood.
Must hear: “Never Dreamed You’d Leave In Summer”

17: Kristina Train: Dark Black (Mercury, 2012)

A soulful-voiced New York-born singer-songwriter who relocated to London after an album deal with Blue Note turned sour, Train created a noir-esque melancholic masterpiece with this, her second – and, to date, finest – album. The prevailing mood is somber, but not depressingly so. Dark Black’s sable-hued majesty is encapsulated by the title song, a haunting ode to lost love. Whether her material is autobiographical or not, Train’s vocals make it clear that she’s someone who’s stared heartbreak straight in the face.
Must hear: “Dark Black”

16: PJ Harvey: Rid Of Me (Island, 1993)

For some, a broken romance inspires feelings of hatred, bitterness, and even revenge for perceived wrongdoings. On the autobiographical title track from Polly Jean Harvey’s second album, the high priestess of grungy alt.rock reflects on a relationship with a rabid and almost psychotic glee. “You’re not rid of me,” she wails, then threatens to twist her paramour’s head off. With the rest of the album executed at the same level of high-pitched vitriolic intensity, this is the go-to record for those who react to romantic betrayal with anger rather than self-pity.
Must hear: “Rid Of Me”

15: Billie Holiday: Lady Sings The Blues (Clef, 1956)

Such was Billie Holiday’s talent as a conveyor of deep emotion that she could sing two notes and conjure up a whole galaxy of hurt and heartbreak. On this classic album, every melody she caresses tells a story, etching a vivid autobiographical narrative characterized by bad relationships and abusive lovers against a seedy backdrop of drug and alcohol abuse. For those who find comfort in melancholy, this is the break-up album to wallow in.
Must hear: “Good Morning Heartache”

14: Adele: 21 (XL, 2011)

Adele cancelled the initial recording sessions for her second album, claiming that she was bereft of inspiration, but her creative muse returned when she split up with her boyfriend. The singer’s acute sense of loss and heartbreak prompted her to examine her emotional scars and pour out her feelings in a variety of songs, ranging from the scornful “Rolling In The Deep” and the confrontational “Take It All” to the more contemplative and overwhelmingly poignant “Someone Like You.”
Must hear: “Someone Like You”

13: Frightened Rabbit: The Midnight Organ Fight (Atlantic, 2007)

Fronted by the poet laureate of despair, the late Scott Hutchinson, Scottish indie rockers Frightened Rabbit served up a raw and nakedly honest dissection of a cancerous love. Purportedly based on Hutchinson’s personal life, the album’s 14 tunes are unremittingly bleak and yet brilliantly written, couched in memorable and at times uplifting melodies.
Must hear: “The Modern Leper”

12: Roy Orbison: Lonely & Blue (Monument, 1961)

With song titles such as “I’m Hurtin,”” “Bye Bye Love,” “Cry,” “Blue Avenue” and “Come Back To Me (My Love),” it’s evident that Orbison’s debut album wasn’t going to be a cheerful affair. Instead of waxing lyrical about the unalloyed joys of romance, Lonely & Blue is, mostly, a catalogue of pain, misery and loneliness caused by Cupid’s arrow and a host of cruel paramours. Despair never sounded so beautiful.
Must hear: “Only The Lonely”

11: Bon Iver: For Emma, Forever Ago (Jagjauwar/4AD, 2008)

Before they became a fully-fledged indie folk-rock band, Bon Iver consisted solely of singer-songwriter Justin Vernon, who masterminded this haunting debut album. Reflecting on a past love affair, he sought emotional closure by pouring his heart out in nine songs written while he shacked up in a Wisconsin hunting cabin. The result was a break-up album that was by turns achingly desolate and soul-searchingly magical.
Must hear: “re:stacks”

10: Beck Sea Change (Geffen, 2002)

A devastating break-up following his long-time girlfriend’s infidelity inspired this, the maverick auteur’s eighth album. Eschewing the quirky, sample-dominated sound of his previous work, Beck opted for a more organic, acoustic-guitar-led singer-songwriter approach with orchestral strings adding a touch of somber grandeur. The approach gave his songs of mourning, isolation, and heartbreak a deeper resonance.
Must hear: “Lonesome Tears”

9: Kanye West: 808s & Heartbreak (Def Jam, 2008)

Understandably, Kanye West’s world imploded when his mother died in 2008. Shortly afterward, his sense of loss was further exacerbated when his fiancée dumped him. Those two events, coupled with the rapper’s ambivalence towards his growing fame, were reflected in the tone and themes of this, his fourth album. 808s & Heartbreak was stylistically different, too, from the hip-hop norm, using synth-heavy electronic soundscapes as a backdrop over which West sang as well as rapped. Broodingly melancholic and deeply personal, the album showed how grief could be channeled into liberating, boundary-breaking music.
Must track: “Heartless”

8: Richard & Linda Thompson: Shoot Out The Lights (Hannibal,1982)

Much lauded by the critics and a frequent high-ranker in best-albums lists compiled by influential magazines like Rolling Stone and Q, Shoot Out The Lights was the British husband-and-wife duo’s sixth and final record together. Ironically, though, its creation accelerated the demise of their marriage, which is dissected in eight songs. Though a scintilla of hope for the couple manifests itself in the opening song, “Don’t Renege On Our Love,” there’s a sense of doom, desperation and chilling finality on the closing “Wall Of Death.”
Must hear: “Don’t Renege On Our Love”

7: Joni Mitchell: Blue (Asylum, 1971)

Arguably the Canadian singer-songwriter’s most eloquent and nakedly emotional album, Blue was Mitchell’s response to two break-ups: one with ex-Hollies member Graham Nash, the other with American singer-songwriter James Taylor. The latter relationship began in Europe, where Mitchell wrote most of the album trying to get over Nash. She broke up with Taylor not long after, but that gave Mitchell the impetus to finish an album whose simple title and cobalt-tinted cover encapsulates the mournful essence of lost love.
Must hear: “A Case Of You”

6: Bruce Springsteen: Tunnel Of Love (Columbia, 1987)

The rock embodiment of the blue-collar American everyman, The Boss gritted his teeth and bared his soul on this album, which chronicled his disintegrating marriage to actress Julianne Phillips. Its angst-ridden themes of deceit, betrayal, doubt, and heartbreak were so personal to Springsteen that he recorded much of the music by himself without his trusted sidekicks, The E Street Band. A bleak post-mortem of tainted love, this cathartic opus fails to reveal even the smallest chink of light and hope at the end of its dark tunnel.
Must hear: “Brilliant Disguise”

5: Frank Sinatra: Frank Sinatra Sings For Only The Lonely (Capitol, 1958)

Though he projected a hard-nosed, tough-guy image, in real life Sinatra was as vulnerable as the rest of us and no stranger to the pain of heartbreak. His break-up with – and subsequent divorce from – actress Ava Gardner in 1957 affected him badly and proved the inspiration for this, one of Sinatra’s darkest but also most brilliant albums. An exquisite paean to lost love.
Must hear: “One For My Baby (And One More For The Road)”

4: Willie Nelson: Phases & Stages (Atlantic, 1974)

The Texas troubadour broke new ground for country music with this ambitious concept album about divorce and its repercussions. It came in the wake of Nelson’s break-up with his second wife, singer Shirley Collie, after he had an affair, and explores the trauma of separation from both a man and a woman’s perspective. Nelson offers a double narrative, split over two sides of the album, exploring feelings from both sides of the emotional divide. To his credit, his songs elicit pathos without resorting to self-pity.
Must hear: “Bloody Mary Morning”

4: Bob Dylan: Blood On The Tracks (Columbia, 1975)

Dylan was adamant that he didn’t write soul-baring confessionals and categorically denied that Blood On The Tracks was about his painful split from his first wife, Sara, going so far as to claim it was a collection of songs inspired by Anton Chekhov’s short stories. Many commentators, though, contend that the album is autobiographical (even the songwriter’s son Jakob agreed, declaring in 2006, “that’s about my parents”). Whatever its inspirational source, Blood On The Tracks explores themes of heartbreak, loss, and separation in both an eloquent and tender way on tracks like “Idiot Wind” and “Simple Twist of Fate.”
Must hear: “Simple Twist Of Fate”

3: Marvin Gaye: Here, My Dear (Tamla, 1978)

Out of the ugliness of Marvin Gaye’s acrimonious divorce from Anna Gordy, in 1977, something beautiful emerged: Here, My Dear, a warts’n’all autobiographical album that graphically chronicled his failed marriage to Berry Gordy’s sister, a woman 17 years Gaye’s senior. Given that Gaye wasn’t going to profit financially from the album – he had agreed to hand over the proceeds to his ex-wife, in order to settle spiralling divorce costs – he surprisingly poured his heart and soul into the project, creating an inspired confessional that grew into one of the best break-up albums ever.
Must hear: “When Did You Stop Loving Me, When Did I Stop Loving You”

2: Amy Winehouse: Back To Black (Island, 2006)

By documenting her toxic relationship with, and separation from, her on-off beau Blake Fielder-Civil, the troubled Camden-born R&B singer-songwriter created a scintillating, Grammy-winning break-up masterpiece. Track titles like “Rehab” and “Tears Dry On Their Own” give you a clue as to what to expect. Back To Black is a compelling music-as-therapy self-help manual that tackles themes of heartbreak, separation, loss, depression, infidelity, guilt, and addiction. The album’s raw honesty struck a chord with listeners everywhere, converting Winehouse’s grief into sales of 16 million.
Must hear: “Love Is A Losing Game”

1: Fleetwood Mac: Rumours (Warner Bros, 1977)

Topping our list of best break-up albums of all time is Fleetwood Mac’s magnum opus. At the time of recording, the band was in turmoil: John McVie and his wife, Christine, had just divorced, while Stevie Nicks and Lindsey Buckingham’s romance was dissolving into acrimony. To cap it all, the group’s leader, drummer and co-founder, Mick Fleetwood, discovered his wife had had an affair with his best friend (but that didn’t stop him jumping into the sack with Nicks). Given this background of near-incestuous domestic strife, distrust, and broken relationships, Rumours should have been an unmitigated disaster, but the band’s need to make music had a cathartic effect that created a healing bond of unity instead of discord. Their pain was transmuted into a soft-rock masterpiece on tracks like “Dreams” and “Go Your Own Way.”
Must hear: “Dreams”

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  1. Jay

    February 12, 2020 at 10:28 pm

    First, you missed “Hearts and Bones,” Paul Simon’s heartbreaking farewell to Carrie Fisher.

    Second, where’s Leonard Cohen? Either “Songs of Love and Hate” or “New Skin For the Old Ceremony” belongs on here.

    Regarding “Blue” which I would put second, behind only “Blood on the Tracks,” it was not about her breakup with JT–that was “For the Roses”; “Blue” dealt mostly with Nash, but also Leonard Cohen (“A Case of You”), Cary Raditz (“Carey,” and “California”), the daughter she gave up for adoption (“Little Green”), and her ex-husband Chuck (“The Last Time I Saw Richard”).

    A nice list nonetheless.

  2. Tatiana

    February 14, 2020 at 11:41 pm

    You forgot ‘I Never Learn’ by Lykke Li

  3. David

    December 15, 2020 at 7:36 pm

    Crushing by Julia Jacklin would definitely be on my list, one of the mos beautiful albums of 2019 in my opinion.

  4. Craig

    June 9, 2021 at 7:47 pm

    Olivia Rodrigo just had to release SOUR and invalidate this list a short few months later, didn’t she? Blood on the Tracks a close second, though I admittedly haven’t heard everything on this list.

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