The 20 Best Breakup Songs of the 90s

Whitney Houston

There’s a time and a place for love songs, but a break-up isn’t it. When a relationship fizzles out, there’s comfort in knowing that someone else has been there, seen that, and written the song to prove it. Not that all breakup songs wallow in the misery, of course (although there’s nothing wrong with those that do). For every song that laments the passing of a relationship, there’s another that celebrates it. Whether you want to grieve at the passing of love or burn the very concept to the ground, these are the 20 best breakup songs of the 90s to do it too.

20. All Saints – Never Ever


For a while in the 90s, it was touch and go as to whether the Spice Girl or All Saints would emerge as the bigger band. Obviously, the Spice Girls won the war, but All Saints put up a good fight, not least on Never Ever, a sultry breakup song that ran all the way to the top of the charts in Australia, New Zealand, and the United Kingdom on its release in November 1997.

19. Macy Gray – I Try


No matter how hard you try, some breakups are impossible to get over. Macy Gray knew it, and in 1999, she dominated the airwaves singing about it. I Try, the second single from her debut album, On How Life Is, was an international hit, peaking at No.6 in the United Kingdom, No. 5 in the US, No. 2 in Canada, and No.1 in Australia, Ireland, and New Zealand.

18. Oasis – Don’t Look Back In Anger


It’s always easy to look back in anger after a breakup, but in the 1990s, Oasis scored a No. 1 hit for preaching the opposite. Released in 1995 as the first Oasis single to feature lead vocals from Noel Gallagher rather than his brother Liam, it sailed to the top of the charts in the UK. Since it was spontaneously sung at the memorial of the Manchester Arena bombing in 2017, it’s taken on a new significance that transcends its original life as a breakup song.

17. Mariah Carey – Without You


Badfinger wrote Without You, Harry Nilsson popularized it, and Mariah Carey made it iconic. Released in 1993, it perfectly describes that feeling you get at the end of a relationship when nothing seems to have a point anymore.

16. Aerosmith – Cryin’


No list of breakup songs would be complete without at least one Aerosmith song. Here, we’ve gone for Cryin’, a song that’s as much about the 90s (the video even has Alicia Silverstone, and it doesn’t get much more 90s than that) as it is about the pain of a breakup.

15. Mary J. Blige – I’m Going Down


I’m Going Down was originally performed by Rose Royce for the 1976 Car Wash soundtrack. Two decades later, Mary J. Blige transformed the torch ballad into a slice of R&B gold on her seminal 1994 album My Life. If you’ve ever been through a breakup, Blige’s soaring, soulful vocals will transport you back to the pain and the loneliness in a heartbeat.

14. Cher – Believe


In 1998, Cher unveiled her latest reinvention as a dance-pop diva. The tune that ushered in the new era was Believe, a song that’s best remembered for being one of the very first to ever employ Auto-Tune, but which, at heart, is a good, old fashioned breakup song with a style and an attitude that’s almost reminiscent of Gloria Gaynor’s I Will Survive. “I’ve had time to think it through / And maybe I’m too good for you,” Cher warbles, thus inspiring several million spurned lovers to quit crying and start getting on with their lives.

13. Natalie Imbruglia – Torn


Named by Bustle as one of the best break-up songs of the 90s, Torn was originally recorded by American alt-rockers Ednaswap, but it took Aussie Natalie Imbruglia to turn it into a global hit. Her emotional delivery perfectly captures the inevitable moment you realize the honeymoon is over and wake up to the fact that “Illusion never changed / Into something real.”

12. TLC – Switch


Back in the 1990s, you didn’t mess with TLC. Try, and they’d come round your house and stamp on your toys. On Switch, they’re too busy telling their possessive ex-lovers to take a running jump to waste time lamenting the end of the relationship. It’s tough and ballsy, and the perfect counterfoil to every weepy, lovelorn ballad ever written. Its accompanying album certified diamond (the first by any girl group to ever be awarded the status) and the song gave everyone who’s ever felt repressed by their partner a new slogan: erase, replace, embrace, new face.

11. Gang Starr – Ex Girl to Next Girl


As The Guardian writes, hip-hop isn’t big on romantic heartbreak, but in 1992, Gang Starr bucked the trend and gave us a particularly fine example in the shape of Ex Girl to Next Girl. Guu spends a lot of time bleating about the number of offers he’s had since his ex showed him the door, but you can’t help but think the gentleman doth protest too much.

10. Lauryn Hill – Ex-Factor


The Miseducation of Lauryn Hill was about a lot more than Doo Wop (That Thing). Ex-Factor is about the longing for things that can’t be and the frustration and anguish of a love that refuses to die. It’s deep stuff, but the languid, luscious rhythm and enchanting vocals keep things grooving. Released as the second single from Hill’s debut album, it broke the Top 40 on the Billboard Hot 100 and soared to number one on both the US R&B/Hip-Hop Airplay and on the UK R&B chart.

9. Alanis Morissette – You Oughta Know


As says, Alanis Morissette’s third studio album sent shock waves through the music industry. Never before had a singer poured their anger and pain into a collection of songs quite so freely, nor quite so explicitly. Who she’s raging about on You Oughta Know (most people have pinned it on “Full House” star Dave Coulier) doesn’t actually matter too much: the searing anger and vengeful pain of the scored lover is what drives the song, not the lover themselves. Released as the lead single from Jagged Little Pill in July 1995, it broke the top ten in Canada, Australia and the United States.

8. No Doubt – Don’t Speak


When Gwen Stefani and bassist Tony Kanal broke up after seven years together, the No Doubt frontwoman poured all of her pain into Don’t Speak, a heartbreaking song that spoke to enough lovelorn souls to spend 16 weeks at number one on the Hot 100 Airplay chart as well as topping the charts in Australia, Canada, Iceland, the Netherlands, New Zealand, the Republic of Ireland and the United Kingdom. It also managed to pick up nominations for Song of the Year and Best Pop Performance by a Duo or Group with Vocals at the 40th Grammy Awards.

7. Boyz II Men – End of the Road


Boyz II Men might have hit the end of the road in their relationship, but they weren’t prepared to go quietly. They plead, they beg, they reminiscence, but for all that, you still get the feeling they’re singing to a turned back and a resolute mind. Released in 1992, it was a massive worldwide hit, spending a record-breaking 13 weeks at number one on the US Billboard Hot 100 and becoming the sixth most successful song of the decade in terms of sales.

6. Britney Spears – …Baby One More Time

Britney Spears’ first single marked her transition from a Mouseketeers into a bona fide pop sensation. The title and the video drew all kinds of criticism, but essentially, it’s a simple story about a teenage girl longing for the return of an ex-boyfriend. Every teenage girl could relate to it, every man, woman, and child could sing along to it, and over 20 years after its release, it still stands as one of her more popular songs.

5. Jeff Buckley – Last Goodbye


When Jeff Buckley released his first and last studio album Grace in 1994, it barely shifted a copy. Then he died, his legend took off, and it’s now widely considered one of the seminal albums of the decade, if not the 20th century. Its second single, Last Goodbye, tackles the final moments of a dying relationship, at a point when the feelings are still there, but the future isn’t. After landing at No.19 in the Billboard Alternative Song chart, it became Buckley’s most commercially successful song in the US.

4. Annie Lennox – Walking On Broken Glass


After building her career with Eurythmics, Scottish singer Annie Lennox broke free in 1992 to release her debut album Diva. It was a smash hit, peaking at No.1 on the UK Albums Chart and selling over 1.2 million copies in the UK alone. One of its highlights is Walking On Broken Glass, a sophisticated piece of pop that finds Lennox begging her ex to pick up the pieces of her shattered life after their split. Despite the downbeat subject matter, its upbeat tempo and retro soul vocals keep things just the right side of radio-friendly. A global hit, it established Lennox as one of the biggest solo stars of the decade.

3. Toni Braxton – Un-Break My Heart


Un-Break My Heart isn’t just another sad song about a breakup, it’s a phenomenal tour de force that showcases Braxton’s extraordinary vocal prowess and ability to weave a story. From the wistful Spanish guitars to Braxton’s creamy contralto, the whole thing is a triumph, even if it does make your heart feel torn to pieces by the end. Released in October 1996, the song won Best Female Pop Vocal Performance at the 39th Annual Grammy Awards in 1997 and has since gone on to sell over 10 million copies, making it one of the best-selling singles of all time.

2. Sinead O’Connor – Nothing Compares 2 U


It takes a lot of guts to cover a Prince song and more than a little talent to make everyone forget it was him that wrote it in the first place. When Sinead O’Connor covered Nothing Compares 2 U in 1990, she made it her own. As ( notes, her emotional performance – which the starkly intimate music video managed to capture so well – perfectly portrays the pain and heartbreak that comes after a breakup. A worldwide hit, it topped the charts in Ireland, Australia, Austria, Canada, Germany, Mexico, Netherlands, New Zealand, Norway, Sweden, Switzerland, the United Kingdom, and the United States.

1. Whitney Houston – I Will Always Love You

As Time Out writes, I Will Always Love You was originally recorded by Dolly Parton in 1973 and later reprised in the 1982 movie musical “The Best Little Whorehouse in Texas.” Both versions soared to the top of the country charts, but it would take Whitney Houston to turn it into an international juggernaut. Released in 1991 as part of the soundtrack to “The Bodyguard,” the lyrics describe the end of a relationship that, rather than descend into bitterness and turmoil, retains a noble dignity. The song spent a then-record-breaking 14 weeks at number one on the Billboard Hot 100 chart and remains one of the best-selling singles of all time to this day.

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