16 of the Most Heartbreaking Albums of All Time
From Taylor Swift to Leonard Cohen, explore 16 of the most heartbreaking albums ever made.
If the three-and-a-half minute pop song is the perfect length for a declaration of love, then the long-playing album is the perfect length to really wallow in the sorrow of a heartbreak. Over the years, countless great albums have been born from the fallout of breakups or lost loves – more than we could possibly list. From the classics to the lesser knowns, this list of heartbreak albums can offer sympathy, commiseration, or (at least) a soundtrack to anyone not celebrating Valentine’s Day – as well as the encouraging reminder that great, timeless art can come from even the worst heartbreak.
Famously recorded amid relationship turmoil between several members of the band, Fleetwood Mac’s Rumours is often cited as one of the greatest albums of all time – but it also put severe emotional strain on the group. Keyboardist/vocalist Christine McVie and bass guitarist John McVie had recently divorced after eight years of marriage, and had stopped talking unless it concerned music, while guitarist/vocalist Lindsey Buckingham and vocalist Stevie Nicks endured an on/off relationship that often flared up. Meanwhile, drummer Mick Fleetwood had recently discovered that his wife was having an affair. The emotional tensions within the recording sessions produced a bittersweet, soap-operatic masterpiece that has sold over 40 million copies to date. According to Nicks, Fleetwood Mac created the best music when in the worst shape, and this is abundantly clear on tracks such as “Go Your Own Way” and “The Chain.”
Taylor Swift’s folklore is an album full of quietly, devastating ballads about loss, betrayal, and heartache. The bridge of “my tears ricochet,” (“and I can go anywhere I want/anywhere I want/just not home”) describes the heart-wrenching feeling of emptiness when someone you loved is irreversibly gone. There’s “exile,” with its haunting repeated refrain – “you never gave a warning sign/I gave so many signs” – that will be all too familiar to anyone who’s begged a partner, to no avail, to see that a relationship is dying. Finally, there’s “hoax,” which speaks to how hopeless life can feel after loss with its chorus, “stood on the cliffside/screaming ‘give me a reason’/your faithless love’s the only hoax I believe in.”
SZA’s SOS opens with a Morse code distress call backed by a gospel sample, setting the tone for a record that sees the singer struggling with self-determination in the midst of self-doubt. On SOS, SZA is unable to cultivate the kind of love she wants in her romantic relationships, or even in her relationship with herself — one minute, she’s worthy and self-assured (“Smoking On My Ex Pack,” “Forgiveless”); in the next, she’s trapped in a destructive back-and-forth (“Seek & Destroy,” “Blind”). In her most relatable work yet, SZA devotes time, space, and her unfettered emotion to love’s universal experience.
Debut album Dummy put Portishead on the map, but their late-career follow-up Third may be even more melancholic and heartbreaking. Beth Gibbons’ haunting vocals and the band’s brooding atmospherics and claustrophobic builds are the audio embodiment of a broken heart. The lyrics delve into the depths, with songs like “Silence,” “Nylon Smile,” and “The Rip” evoking a loneliness and self-doubt that only comes with profound loss. Tapping into feelings of paranoia and dissociation, Gibbons creates a sense of detachment even within the album’s ominous drama. When the only way out is through, Third is an ideal soundtrack for navigating the darkest corners of despair.
In a discography with no shortage of heartbreakingly sad albums, Mount Eerie’s Dawn still stands as a singularly powerful breakup album. The story goes: following a break-up and the retirement of his previous recording moniker the Microphones, Phil Elverum retreated to a cabin in remote northern Norway where he lived alone for a long, dark winter, going for walks in the snow, gathering water and chopping wood, taking photographs, keeping a journal – and writing songs on his acoustic guitar. As with the Microphones, these songs – featuring only Elverum’s clear, quavering singing voice and that guitar – map emotional and existential introspection to a sense of holy wonder at the natural world and the universe, with songs like “Moon Sequel” directly recalling his past works. The songs of Dawn cycle through love, loss, the lonesomeness of that frozen winter, and even bitter regret, but they ultimately arrive at a place of serene catharsis on songs like “Cimb Over,” ready to reenter the world with a healed and open heart. Originally released on both vinyl and as a CD packaged with Elverum’s “winter journal” as a hardbound book, the album was repressed with a fold-out poster containing the journal’s full text.
No matter what stage of heartbreak you’re in, Beyoncé’s Lemonade has a song for it. Her sixth studio album takes listeners on an emotional journey through her partner Jay-Z’s infidelity. From the denial of “Hold Up” (“What’s worst, lookin’ jealous or crazy?”) to the anger of “Sorry,” (“middle fingers up/put them hands high/wave it in his face/tell him, boy, bye”) to the acceptance of “Don’t Hurt Yourself” (“keep your money/I got my own/get a bigger smile on my face/being alone”), every song on this phenomenal album packs a punch. As Beyoncé herself said about the album, “Everyone experiences pain, but sometimes you need to be uncomfortable to transform.”
Kacey Musgraves challenges conventional country music breakup tropes on her fifth-studio album Star-Crossed. Using a three-act structure, she chronicles her marriage to and divorce from singer-songwriter Ruston Kelly, painting the pair as star-crossed lovers destined to end their relationship in tragedy. Musgraves writes candidly about her struggle to maintain traditional gender roles (“Good Wife”) and her experience of jealousy from her partner (“Breadwinner”). Though she admits that “healing doesn’t happen in a straight line,” Musgraves finds herself whole and triumphant on the other side of heartbreak.
Blood on the Tracks
At the end of his 1974 tour with the Band, Bob Dylan began a relationship with Columbia Records employee Ellen Bernstein, ushering in the end of his marriage to his then wife Sara. Simultaneously, Dylan attended art classes with the painter Norman Rueben, who helped him transform his understanding of time. Dylan began penning new songs in his notebook. “[Raeben] taught me how to see […] in a way that allowed me to consciously do what I unconsciously felt,” said Dylan. “When I started doing it, the first album I made was Blood On The Tracks.” Recorded between New York and Minneapolis, Blood On The Tracks is often cited as one of Dylan’s best, featuring songs that echo emotional tensions in Dylan’s personal life. Though Dylan has denied that the songs are autobiographical, son Jakob Dylan has described the album by saying, “That’s my parents talking.”
Tyler, the Creator
In a departure from his usual antagonistic bars about the music industry, his parents, and other targets, Igor finds Tyler, the Creator diving deep into feelings of heartbreak and confusion as he reflects on a breakup with a man who left him for a female partner. The album’s synth-heavy funk and neo-soul support the rapper’s narratives about unrequited love as he struggles to maintain his own identity within and without this relationship. The songs on Igor — written, produced, and arranged by Tyler — begin with climaxes, lack natural endings, and have throughlines that never resolve, creating an unsettled, uncertain atmosphere similar to the experience of giving all of yourself to a romance that doesn’t work out.
King Midas Sound
Released at midnight on Valentine’s Day in 2019, King Midas Sound’s Solitude is a collaboration between experimental electronic producer Kevin Martin (the Bug, Techno Animal) and the British-Trinidadian poet Roger Robinson. Over 12 desolate, windswept tracks of ambient electronic dub, Robinson’s spoken word meticulously depicts the unraveling of a relationship and the namesake solitude left in its wake, wallowing in the sharply remembered details, lying awake imagining an ex-lover with someone new, obsessing and spiraling. It is at times a brutal listen, a loneliness laid bare to the point of breaking, as on midway point “Alone,” a track which consists of little more than a seasick echo of a foghorn and Robinson repeatedly intoning the track’s title in his basso profundo speaking voice. Perhaps uniquely for the albums on this list, there is hardly a hint of catharsis here; rather, Solitude imagines itself as endless and all-consuming. Not for the faint of heart.
Nick Cave & The Bad Seeds
The Boatman’s Call
The Boatman’s Call was a major departure for Nick Cave & The Bad Seeds as they moved away from the chaos and character-driven narratives of their earlier material to embrace spare piano arrangements and more personally vulnerable lyrics. Slower tempos and sparse compositions put the emphasis on Cave’s commanding voice and the lyrics’ frank depictions of failed romantic relationships. Inspired by Cave’s divorce from ex-wife Viviane Carneiro, as well as the dissolution of his brief relationship with PJ Harvey, the romance and heartache of these songs make The Boatman’s Call a deeply personal exploration of love’s beauty and its devastating ends.
Rid of Me
Following the release of Dry in 1992, PJ Harvey toured extensively through the U.S. and U.K. She was offered a spot on that year’s Lollapalooza Tour, but turned it down, citing exhaustion, poor nutrition, and a recent break up. Instead, Harvey left London for Dorset, where she started writing songs for Rid of Me. According to Harvey, the title track from the album openly addressed the break up in its raw, loud/soft dynamics, and was written “at my illest,” adding that she was “almost psychotic at the time.” Harvey and her band recorded the album at Pachyderm Studios in Minnesota with sound engineer Steve Albini, and finished the bulk of the recording in three days. According to Harvey, “You can feel the sound [Albini] records, and this is why I wanted to work with him.” Perhaps this is why Rid of Me delivers the brutality of heartbreak with such intensity, transforming Harvey’s pain into power.
FKA Twigs’ second studio album Magdalene is all about sensuality, strength, and resilience. Inspired by the singer’s breakup with actor Robert Pattinson, Magdalene explores themes of love, loss, and recovery backed by experimental electronic, pop, and R&B compositions. Here, Twigs’ emotionally raw vocal performances are second only to her vulnerable storytelling, which gives the “impression of someone knitting themselves back together after coming undone.” On the album’s standout track “Cellophane,” Twigs sings about her fears of rejection and yearning for love and acceptance, while “Sad Day” chronicles her attempts to mend an already broken relationship.
Songs Of Leonard Cohen
Leonard Cohen began his career as a novelist and poet, but lack of success as a writer inspired him to pursue a career as a folk singer-songwriter. Pairing evocative prose and poetry with intricate fingerpicking and a smoky bass-baritone, Cohen recorded a landmark debut that is deeply sensual, romantic, and remorseful. Tracks like “Suzanne,” “So Long, Marianne,” and “Hey, That’s No Way to Say Goodbye” move through lust, love, and loss with a level of detail that may only be rivaled by the poetic prowess of Bob Dylan. The intimate feel of the recording adds to the album’s somber mood and sexuality, which eventually led to Cohen being referred to as “the master of erotic despair.” For anyone seeking an album that confront love’s rawest edges, Songs Of Leonard Cohen is as cathartic as they come.
If you’re looking to dance your heartbreak away, look no further than Robyn‘s album Body Talk. Inspired by her favorite “inherently sad gay disco anthems,” the Swedish singer’s seventh album is full of hits, like “Dancing On My Own” and “Call Your Girlfriend,” that demand singing and dancing along to their electro-pop pulse and heartfelt lyrics. Nowhere is this more irresistible than on the chorus of “Call Your Girlfriend,” with its instruction,
“Call your girlfriend
It’s time you had the talk
Give your reasons
Say it’s not her fault
But you just met somebody new.”
Emerging from the art-damaged, DIY punk scene centered around Los Angeles venue The Smell in the early ‘00s, Brendan Fowler’s BARR project combined self-referential spoken word with seemingly tossed-off yet surprisingly catchy indie instrumentals on drums, piano, and guitar. While the sole full-length Summary covers a variety of subjects and scenes, including meditations on music and art making, creation and absence, its centerpiece is the monumental breakup track “Complete Consumption of Us Both.” Over a steady bass drum pulse, Fowler relates the mundane and devastating aftermaths of a breakup: the staking out of newly separate worlds, coordinating to avoid each other while both shopping to furnish separate apartments, all culminating in a chanted refrain of “catharsis is real” that sounds surprised at its own self-evident, self-actualizing truth. There’s echoes of this dissolution all over the album, such as on stuttering awkwardness of “Was I? Are You?,” but Summary situates its loss in the midst of a creative world overflowing with possibility and abundance, where loss becomes just so much more material for self-transformation and artistic invention.
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