Top 10 greatest break-up songs of all time
Move over Taylor Swift — Lily Allen’s blistering new album turns her split into a lyrical bloodsport, and has us revisiting the greatest breakup songs of all time.
In her first album in seven years, Lily Allen so completely and utterly eviscerates her now ex British singer David Harbour that it’s a wonder he’s not on a ventilator in a hospital somewhere.
Billed as a “divorce album”, West End Girl charts a linear timeline from the bliss of marriage with the Stranger Things actor, to moving from the UK to the US with her two daughters so they could all be together, through to the heartbreak of a relationship breakdown.
It even details Allen reluctantly agreeing to an open relationship and almost relapsing into addiction.
A sample of the stinging lyrics are: “Who said romance isn’t dead / Been no romance since we wed / ‘Why aren’t we f...ing, baby?’ / Yeah, that’s what you said” and “Why are we here talking about vasectomies? / Did you get someone pregnant? / Someone who isn’t me? / Did you take her to the clinic? / Did you hold her hand? / Is she having your baby?”
Some of the most shocking lyrics are from the song Pussy Palace, where the singer describes kicking Harbour out of the house and visiting him at his new abode, and finding sex toys.
In honour of the singer’s brutal honesty on her album, here are the top 10 greatest break-up songs of all time, comprised with the help of Billboard’s top 100 break-up songs.
1. You Oughta Know by Alanis Morissette
Who knew Uncle Joey from Full House could evoke such a passionate response to a break-up?
Released in 1995, Alanis Morissette’s first single You Oughta Know from album Jagged Little Pill caused a stir with its raw lyrics, including “And every time I scratch my nails / Down someone else’s back, I hope you feel it / Now can you feel it?”.
It was later revealed the song was about actor Dave Coulier, best known as the uncle who is not John Stamos from Full House.
Coulier and Morissette dated from 1992 to 1994, with the actor saying they are now on good terms.
2. I Will Always Love You by Dolly Parton (and Whitney Houston)
Depending on your age, you would either think I Will Always Love You is sung by Dolly Parton (in 1974) or Whitney Houston (in 1992, from the movie The Bodyguard).
Any which way, this heartbreaking song was originally sung by Parton as a tribute to her business partner, who she was leaving to start a solo career.
The ballad was revived in the movie The Bodyguard, where Houston played a pop star receiving threats and Kevin Costner played her brooding bodyguard.
3. Someone Like You by Adele
Written after a boyfriend broke up with her and moved on with someone else, Adele’s heart-rending 2011 song Someone Like You remains one of her most popular, with a staggering two billion streams on Spotify.
“After I wrote it, I felt more at peace. It set me free,” Adele has said of her hit song. “I didn’t think it would resonate with the world! I’m never gonna write a song like that again. I think that’s the song I’ll be known for.”
4. All Too Well by Taylor Swift
Would a list of break-up songs be complete if Taylor Swift wasn’t on it?
There are an array to choose from but perhaps her most well-known is All Too Well, supposedly about actor Jake Gyllenhaal, whom Swift dated in 2010.
In the 2021 re-release of the song, which was an updated 10-minute version, the additional lyrics seemed to strongly suggest it was indeed about the Brokeback Mountain actor.
The additional lyrics referenced their three-month romance and Gyllenhaal missing Swift’s 21st birthday.
For his part, the actor has continued to deny the song is about him and, as is her M.O., Swift has never confirmed nor denied anything.
5. Nothing Compares To You by Prince (and Sinéad O’Connor)
Although Sinéad O’Connor’s version of Nothing Compares To You is superior to Prince’s version in every way, the original song was written by Prince for a 1985 album.
Nobody noticed the heartwrenching song until O’Connor recorded her own version of it in 1990, and it became an instant global hit.
Equally iconic was the video clip accompanying the song, featuring a close up of O’Connor’s stunning face singing her emotional song.
6. Since U Been Gone by Kelly Clarkson
Considered by critics as one of the greatest pop songs of all time and a constant on the break-up lists, powerhouse vocalist Kelly Clarkson wasn’t even supposed to sing Since U Been Gone originally.
The song about a woman’s relief and freedom after being in a troubled relationship was written for pop artist Pink, who turned it down. It was then given to Hilary Duff, who couldn’t reach the high notes.
Legendary producer Clive Davis stepped in and told the writers that it should be given to Clarkson.
And thank goodness for that.
7. Cry Me A River by Justin Timberlake
Justin Timberlake is probably crying rivers over his stalled career and legal woes, but back in 2002 he was in fine form with this savage break-up anthem about a man moving on from an ex.
Since Cry Me A River was released on the heels of Timberlake’s relationship breakdown with Britney Spears – the pair dated from 1999 to 2002 – many people were quick to connect the dots that the song was about Spears, although Timberlake did not confirm anything at the time.
Many years later, he revealed the song was “inspired” by Spears. For her part, Spears wrote in her 2023 memoir that the true story of their break-up was vastly different to how Timberlake portrayed it.
8. Un-break My Heart by Toni Braxton
Written by the queen of lyrics Diane Warren, Un-break My Heart is a sad song about a woman begging for an ex-partner to return.
Singer Toni Braxton initially “hated” the song because she didn’t want to sing another heartbreak tune, but it ended up becoming her most commercially successful, award-winning song in her entire music career.
9. You’re So Vain by Carly Simon
Carly Simon has famously said 1972’s You’re So Vain, a song about a self-absorbed ex-lover, is about three men.
She has only ever confirmed one of them: actor Warren Beatty. It’s probably not something to be proud of, but Beatty seemed unphased.
Other famous names linked to the song are Mick Jagger, David Bowie, Jack Nicholson, Kris Kristofferson and Cat Stevens.
10. Back To Black by Amy Winehouse
The late singer’s searing 2006 heartbreak anthem was both brutal (“He left no time to regret / Kept his dick wet / With his same old safe bet”) and haunting (“We only said goodbye with words / I died a hundred times / You go back to her / And I go back to us”).
Back To Black was Winehouse’s account of her on-again, off-again relationship with husband Blake Fielder-Civil, who she married in 2007 and divorced in 2009.
The break-up song recounted a dark time for the singer, after Fielder-Civil briefly returned to a former girlfriend.
Winehouse died in 2011 from alcohol poisoning. She was 27.
More Coverage
Originally published as Top 10 greatest break-up songs of all time
Join the conversation
‘WTF?’: Gaga’s Aussie act baffles internet
Read more
Taylor Swift breaks down in tears on screen
Read more