Unless you’re a total sociopath, or just a straight-up lucky person, you’ve felt the effects of heartbreak. It’s one of those things that binds us human beings — sort of like the desire to have chocolate after sex or the feeling one gets after taking a warm shower after running around in the cold rain. When it comes to music, it’s a universal language that connects listeners to distant singer-songwriters, allowing us to feel as if they’re one of us, one of us, gooble gobble, gooble, gobble.

Over the years, there’s been hundreds of albums about heartbreak. A few are iconic — see: Joni Mitchell’s Blue or Bob Dylan’s Blood on the Tracks — while many are ham-fisted at best — see: anything by Simple Plan or Avril Lavigne — and the distinction lies in the ability to make you feel as if what you’re hearing is real. Since a top 10 would likely be chock-full of albums you’ve heard and read about again and again and again, we decided to zero in on the ones that came after the millennium.



As such, there may be a generational divide in the pages ahead. Those who grew up with these albums, especially during their torrential teens or tantalizing twenties, may actually gravitate to them over, say, Frank Sinatra or Alanis Morissette. Then again, these albums are likely iconic enough to cross those lines and affect those kindred souls well into their thirties, forties, and fifties. Again, heartbreak is universal, and these albums speak in all sorts of tongues, both young and old.

The good news is they’re always there. The bad news is … so is heartbreak.

–Michael Roffman

Editor-in-Chief

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10. Sharon Van Etten – Are We There (2014)

Stamp This on a Candy Heart: “We’re as empty as a brick house that we built without the sides,” from “You Know Me Well”

On Are We There, Sharon Van Etten is preternaturally poised. On her fourth studio album, released mid-2014, the singer-songwriter metabolizes the end of a decade-long relationship – one that descended into pain, bitterness, and resentment. That much is obvious from the diamonds that litter the album’s lyrical landscape, lines that glitter and cut. “You say I am genuine/ I see your backhand again,” Van Etten notes on “Our Love”; the chorus of “You Know Me Well” captures how supremely well intimacy can nurture malice. But Van Etten never lets tumultuous emotion drag Are We There into chaos. Her voice is at times wavering, brittle even, but this album’s power stems from how Van Etten has marshaled her feelings to fully communicate the magnitude of her grief and hurt. The towering “Your Love Is Killing Me” is a monument to this sunken relationship, Van Etten delivering its Shakespearean declarations of severance with tremendous gravitas. –Karen Gwee

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09. Lykke Li – I Never Learn (2014)

Stamp This on a Candy Heart: “I let my good one down/ I let my true love die/ I had his heart, but I broke it every time…” from “No Rest for the Wicked”

What to do when your life is falling apart around you? For Swedish singer-songwriter Lykke Li, the answer was to uproot her life and retreat from her home country following a devastating breakup, as if the only cure for her pain was to blow everything up and start again from scratch. Li ended up in the decidedly non-Swedish locale of Los Angeles, where she then spent several years channeling her heartbreak into 2014’s I Never Learn, an album that doesn’t even try to protect the listener from her inner turmoil. And yet, in spite of all the devastation, there’s something powerful here, as if Li has found a way to weaponize her shame and sadness. Songs like “No Rest for the Wicked” and “Gunshot” register with a literal bang, rising above the typical woe-is-me lyricism to achieve an almost sublime kind of despair. I Never Learn is a brutal indictment of self and romantic love, but there’s beauty in the abyss for those brave enough to look. –Collin Brennan

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08. Taylor Swift – Red (2012)

Stamp This on a Candy Heart: “You call me up again just to break me like a promise/ So casually cruel in the name of being honest/ I’m a crumpled up piece of paper lying here, cause I remember it all, all, all too well” from “All Too Well”

As everyone with half a brain knows, Taylor Swift is no stranger to heartbreak. Some might argue it’s what has fueled her music, and they wouldn’t exactly be wrong. After all, her past two blockbuster albums — 2014’s 1989 and 2012’s Red — are tear-stained scrapbooks that chart the startling evolution of one of the world’s most powerful women. Granted, 1989 hasn’t left our rotation since “Shake It Off” dropped down from the pearly gates of pop heaven, but if we’re talking strictly about heartbreak, there isn’t a more palpable album from her than Red. “All the different emotions that are written about on this album are all pretty much about the kind of tumultuous, crazy, insane, intense, semi-toxic relationships that I’ve experienced in the last two years,” she told her fans prior to the album’s release. She’s right; pick a song — any song — and you’re likely to find something to paste on your wall. What’s more, she hadn’t quite made the jump to globe-trotting pop yet, and the country vibes make these songs feel like they’re happening in your own neighborhood as opposed to somewhere in Times Square. –Michael Roffman

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07. Angel Olsen – Burn Your Fire for No Witness (2014)

Stamp This on a Candy Heart: “If all the trouble in my heart would only mend/ I lost my dream, I lost my reason all again” from “Unfucktheworld”

Lots of artists have breakup albums, but Angel Olsen is having a breakup career. That’s an exaggeration of course, but there might not be a contemporary artist whose music has become as synonymous with heartbreak. What makes Burn Your Fire for No Witness her masterpiece, and a pillar of the form, is her willingness to work through the intricacies of love and its absence through as many angles as there are songs on the record. Opener “Unfucktheworld” finds Olsen admitting that she put all her hopes in her former love and is now dealing with the letdown, with as much emphasis put on her own hopelessness and disappointment as on the actual absence of a specific person. Olsen’s heartache isn’t limited to just the moment; for her, it feels like the world is ending. In contrast is “Iota”, about which Olsen told us “I’m not trying to write a piece about the human condition. It’s more about my human condition.” Covering this spectrum, Olsen creates an album that feels like snapshots of love and pain, each existing in a harmony with each other, with the listener strengthened from experiencing it with her. –Philip Cosores

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06. Ryan Adams – Heartbreaker (2000)

Stamp This on a Candy Heart: “Do you still love me?/ I go to the places where we used to/ I feel sad/ I am out here looking for you” from “Amy”

Frank Sinatra’s In the Wee Small Hours often gets credited as the first modern breakup album. That record’s artwork finds Ol’ Blue Eyes adrift in thought on an empty street corner, just outside the halo of a streetlamp, cigarette limp and sighing. Ryan Adams’ solo debut, Heartbreaker, saw the young songwriter posed like Sinatra’s heir apparent: dazed, cigarette propped between his lips, hand cupped over his heart. But let the needle drop, and Adams’ country-tinged exhale sets him apart quickly. Heartbroken and no longer fronting Whiskeytown, Adams found himself on his own in 2000 with something deeply personal hanging heavy on his chest. Standout “Amy”, purported to be about the publicist of the same name who broke up with Adams, captures the songwriter desperately missing his ex, the delicate accompaniment ebbing and flowing as his thoughts wander and simple meanings shift. Are his sweet memories and desires a beacon to follow or merely a cruel illusion? It’s an answer that might change with each cigarette he lets burn all the way down. Adams’ sad songs may seem overly simple at times, but they capture the complexities of heartbreak in a language we all speak. Nearly two decades on, we still turn to Heartbreaker for guidance, comiseration, and a shoulder to cry on. –Matt Melis

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05. Adele – 21 (2011)

Stamp This on a Candy Heart: “I know I have a fickle heart and a bitterness/ And a wandering eye and a heaviness in my head/ But don’t you remember, don’t you remember?” from “Don’t You Remember”

After the swooning pop hit promise of debut 19, an even more life-changing milestone stepped into Adele’s life: the dissolution of the first serious relationship of her young life. The singer-songwriter’s already heartfelt and soulful style was hardened diamond-sharp, throwing out her plans for a modern, upbeat sophomore album in favor of songs that honored the burning fuel of sadness, anger, and uncertainty that sat at her core. The resultant 21 spawned a coterie of songs perfect for whatever flavor of breakup you might be going through — At fault? Broken and longing? Ready to throw something? Searching for answers? Adele Laurie Blue Adkins has you covered. And as if the raw emotional honesty of her songs isn’t enough, they’re all delivered in that skyscraping, platinum-certified voice, the blue-eyed soul depths of which hold magnitudes, whether on slow, soaring tunes like “Someone Like You” or the fiery roar of “Rolling in the Deep”. The album is not only a breakup masterpiece, but the throne on which Adele ascended to her pop royalty. –Lior Phillips

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04. Kanye West – 808s & Heartbreak (2008)

Stamp This on a Candy Heart: “Happen to be just like moments passin’/ In front of me so I hopped in the cab and/ I paid my fare/ See, I know my destination/ But I’m just not there” from “Street Lights”

Every artist has to evolve. Kanye West’s real graduation came with 2008’s 808s and Heartbreak. At the time, the album was incredibly polarizing, a stony, cold experience that extrapolated on all the sadness and turmoil that had been brewing in West’s mind leading up to its three-week recording session — a marathon by today’s standards. Inspired by the brazen pop of Phil Collins, Gary Numan, and Boy George, West eschewed the arena-level hip-hop of his past three efforts for a dozen bummer jams that meditated on the sudden loss of his mother, Donda West, and his torrential breakup with longtime lover and fiancée Alexis Phifer. Like the phoenix rising from a pile of wintry ashes, West came out stronger than ever, shrink-wrapping some of his sharpest and most transparent poetry over a Roland TR-808 drum machine. The whole thing was unprecedented for its minimalistic production (“Love Lockdown”, “Bad News”) and heart-on-its-sleeve lyrics (“Heartless”, “Coldest Winter”), all of which have informed hip-hop, pop, and alternative music in the years since. To quote Yeezus himself, it’s amazing. –Michael Roffman

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03. Bon Iver – For Emma, Forever Ago (2007)

Stamp This on a Candy Heart: “Go find another lover/ To bring a … to string along!/ With all your lies/ You’re still very lovable” from “For Emma”

The story of Bon Iver’s For Emma, Forever Ago has been mythologized to the point that it feels cliche, which is unfortunate for Justin Vernon, the man it actually happened to. Sent into a spiraling depression by the breakup of his band, persistent health issues, and the ending of a relationship, Vernon returned to the town where he was born and holed himself up in a cabin nearby to record the most important album of his life. The Emma in the title directly refers to the middle name of his ex-girlfriend, but in the course of an album, it stands for moving on from the past. Still, it’s the relationship with Christy Smith that pops up repeatedly on the record, in “Flume”, the song that Vernon has referred to as a catalyst for the entire project and, maybe most famously, on “Skinny Love”, where a relationship withers from a lack of nourishment. On the title track, Vernon includes a discourse between an ending couple, concluding the breakup saga with as much mutual adoration and gratitude as you’re likely to find on record. As he says on closer “Re: Stacks”, “Your love will be safe with me.” –Philip Cosores

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02. Amy Winehouse – Back to Black (2006)

Stamp This on a Candy Heart: “He left no time to regret/ Kept his dick wet/ With his same-old safe bet/ Me and my head high/ And my tears dry/ Get on without my guy…” from “Back to Black”

Amy Winehouse’s second and final studio album starts with a defiant flourish. “They tried to make me go to rehab/ I said, ‘No, no, no,’” recounts the English songstress as Motown-style horns blare in brassy fits of laughter. You can almost hear the champagne bottles popping in the background as Winehouse struts her way through the rest of lead single “Rehab”, but this is less a celebration than a loud, celebratory means of coping with heartache. In fact, Back to Black might be the grooviest, sassiest breakup album of all time, a modern classic of blue-eyed soul that hides its tortured soul behind a Phil Spector-sized Wall of Sound. But not even the finger snaps in “Tears Dry on Their Own”, nor the bouncing piano melody that backs the title track, can dilute the pitch-blackness in Winehouse’s voice. She sings of love as if it’s only a game to win or lose, but the stakes are obviously — and, in hindsight, especially — higher than that. –Collin Brennan

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01. Beck – Sea Change (2002)



Stamp This on a Candy Heart: “Press my face up to the window/ To see how warm it is inside/ See the things that I’ve been missing/ Missing all the time” from “Guess I’m Doing Fine”

Staying the course for Beck has always meant swerving off the road the moment the rest of the world seems to also be traveling in his direction. Most every album in his catalog, if measured by what came before, feels like a drastic stylistic detour, a sea change owing less to an identity crisis and more to a realization that no one style or genre can hope to contain his multitudes. However, the aptly titled Sea Change felt different, even upon first listen. It sounded like, maybe for the first time, Beck had made not the record he wanted to make but the one he needed to. Following the dissolution of his nine-year relationship, the album found Beck baring his broken heart on songs that felt as fragile and vulnerable as the man singing them. On standout “Guess I’m Doing Fine”, we hear that aching loneliness as he wanders through a world that’s left him outside in the cold, all conveyed poignantly through sad imagery like looking longingly in through a familiar window or not being able to hear a bluebird’s sweet song through a pane. With nary a wasted breath and a much deeper voice than heard on his last acoustic offering, Mutations, Sea Change felt like grown-ass folk relating a grown man’s heartbreak. It’s Beck’s most cohesive artistic statement to date and a generation’s best breakup record. –Matt Melis