By Tom W. Clarke
Lily Allen’s new album, West End Girl, released last week, is already a break-up album for the ages. Written at the messy end of her relationship with actor David Harbour, it’s a no-holds-barred exposé on heartbreak and infidelity that sent the world into a tizzy.
It’s the latest in one of music’s most hallowed traditions: the devastation turned triumphant catharsis of the break-up album. But who are the best to ever do it? Get your tissues ready.
Lily Allen’s West End Girl, inspired by her split from actor David Harbour, is a break-up album for the ages, and the latest in a long line.Credit: Mike Coppola/Getty Images
Before the list proper, some honourable mentions: Pet Sounds by The Beach Boys (1966); Tapestry by Carol King (1971); Distintegration by The Cure (1989); Rid Of Me by PJ Harvey (1993); The Boatman’s Call by Nick Cave & the Bad Seeds (1997); For Emma, Forever Ago by Bon Iver (2008); Red by Taylor Swift (2012); and Bleeds by Wednesday (2025).
5. 21 by Adele (2011)
One name. One towering voice. One of the best “I’m-better-off-without-you” albums ever made. Reportedly inspired by her split from photographer Alex Sturrock, Adele’s voice is soaring and awe-inspiring, colossal and spectacular. Her hurt is deep, her soul is wild.
She goes full scorched earth on Rolling In The Deep, simmering with barely contained fury. Rumour Has It and Set Fire To The Rain thunder with feeling and Motown-inspired rhythm, while the twinkling piano ballad, Someone Like You, is devastating but hopeful. The highest selling album of the 21st century because sometimes the only way to heal is to hurt.
4. 808s & Heartbreak by Kanye West (2008)
In simpler times, Kanye’s biggest controversy was that he didn’t rap as much any more. Following the twin losses of his mother’s death and his break-up with fiancée Alexis Phifer, Kanye channelled his agony into an album more melodic and vulnerable than he had ever explored.
Sparse, hazy, introspective, dripping in auto-tune and tears. Where earlier records showcased Kanye the rapper and beat maker, 808s introduced Kanye the poet, the experimental pop producer. Where later records became a monument to ego, 808s Kanye is reflective and honest, and it’s strangely beautiful. Patient zero for a decade of emo rap.
3. Jagged Little Pill by Alanis Morissette (1995)
Is You Oughta Know the best break-up song of the ’90s? Maybe. Is it the most fun? Absolutely. It’s a sledgehammer, bashing through walls and splintering doors. It’s rage and angst and sneering disdain, filtered through a kaleidoscope of extremely mid-’90s grunge-pop.
Jagged Little Pill is a raw and uncompromising portrayal of female sexuality: not just in the explicitness of You Oughta Know, but in the Catholic repression of Forgiven and the advice on You Learn that “when the going gets tough, walk around the house naked”. And while Ironic contains few examples of irony, it does contain the funniest one you’ll ever hear (“It’s like 10,000 spoons, when all you need is a knife”).
2. Back To Black by Amy Winehouse (2006)
Perhaps the most uniquely magnetic artist to emerge in the 2000s, Back To Black is Winehouse’s heartbreaking masterwork, a haunting exploration of infidelity, grief and trauma in the wake of a temporary separation from her troubled husband, Blake Fielder-Civil.
Back To Black is a slow wave of smoke and anguish – a tortured, stunning work of storytelling, fractured and soulful. She’s entrancing and almost intimidatingly cool, a world-weary cynicism shadowing genuine despair. At just 22 years old, Winehouse poured all of herself into a dark and twisted reflection of a relationship in flames, two people clinging to each other as they burn, refusing to let the other escape.
1. Rumours by Fleetwood Mac (1977)
“Thunder only happens when it’s raining …” The music hipster in me tried to choose something else. But sometimes the truth is undeniable, and Rumours is simply the greatest break-up album of all time. It’s certainly the album that is about the most break-ups – Christine and John McVie were mid-divorce, Mick Fleetwood had discovered his wife’s affair, and Stevie Nicks and Lindsay Buckingham were either at each other’s throats or in each other’s beds.
The drama. The infighting. The pain. The absolute bangers. A band on the brink of collapse, somehow finding magic in the chaos. Sometimes it’s staggeringly pretty (Never Going Back Again), sometimes it’s disco perfection (Don’t Stop), sometimes it’s a big “eff you” set to jangly guitars (Go Your Own Way), and sometimes it’s the best song ever written (Dreams). Everyone gets a turn, before erupting into the epic, slow-building cathartic crescendo of The Chain. The marriages weren’t perfect, but hot damn, the album might be.
What’s your favourite break-up album? Let us know in the comments below.
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