14 Break Up Songs From The 90s That Will Make You Cry Your Eyes Out All Over Again

The 90’s was a golden age for the world of pop culture, most notably for their tantalizing music tracks. A popular theme for artists in that era were songs about love and relationships, and ultimately, their soul crushing demise.

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So if you’re reeling from the end of a relationship, pull out your discman and make a mix CD, because we have the ultimate list of break up songs from the 90s.  

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1. “Don’t Speak” by No Doubt (1995)

The Grammy-nominated song was written by No Doubt’s vocalist Gwen Stefani and her brother Eric, about the end of her seven year relationship with her bandmate Tony Kanal.

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2. “Un-Break My Heart” by Toni Braxton (1996)

The music video for this power ballad features Toni Braxton reminiscing about Tyson Beckford while engaging in many typical couple activities, such as fooling around in the swimming pool, playing twister, and giving him a clean shave.

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3. “I Will Always Love You” by Whitney Houston (1992)

Despite gaining immense popularity from the movie, The Body Guard, Whitney Houston actually covered this song from Dolly Parton, which was originally released in 1974.

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4. “End of the Road” by Boyz II Men (1991)

The biggest song of 1991, this Boyz II Men song spent a record-breaking 13 weeks at number one on the US Billboard Hot 100. It was originally written for the Eddie Murphy film, Boomerang.

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5. “It’s All Coming Back To Me Now” by Celine Dion (1996)

Another famous cover, Celine Dion put her own twist on the song initially recorded by girl group, Pandora’s Box in 1989. Meat Loaf would also eventually go on to record a duet version with Norwegian singer, Marion Raven in 2006.

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6. “Nothing Compares 2 U” by Sinead O’Connor (1990)

Renown for Sinead O’Connor’s heart-wrenching vocals, Nothing Compares 2 U was at first written by Prince for his side project, The Family. However, the song wasn’t released as a single and the funk band quickly disintegrated.

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7. “You Oughta Know” by Alanis Morissette (1995)

As heavily rumoured this track was written about Full House actor, Dave Coulier, he said he once asked Alanis Morissette who was the inspiration behind the song.

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Morissette said, “Well, you know it could be a bunch of people. But you can say whatever you want.”

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8. “Not A Dry Eye In The House” by Meat Loaf (1995)

A musical masterpiece, Meat Loaf captured true heartbreak as he recalls the love of his life leaving him through flashbacks, as he mourns on an old theater stage.

9. “Without You” by Mariah Carey (1993)

First recorded by British rock group, Badfinger in 1970, this song has been recorded by over 180 artists, most famously by Harry Nilsson and Mariah Carey. Paul McCarthy once described the track as “the killer song of all time.”

10. “You Were Meant For Me” by Jewel (1996)

Taken from Jewel’s first album, this song was actually a re-make of the her original radio version, the Juan Patino Radio Mix, which was ultimately never released.

11. “Show Me The Meaning Of Being Lonely” by The Backstreet Boys (1999)

The sorrowful pop ballad was nominated for a Grammy during the 43rd Grammy Awards for Best Pop Performance by a Duo or Group with Vocals. They lost to Steely Dan with the song, Cousin Dupree.

12. “Ex-Factor” by Lauryn Hill (1998)

One of Lauryn Hill’s first big hits, it’s rumoured she wrote the song about her ex-boyfriend and former Fugees bandmate, Wyclef Jean.

13. “From The Bottom Of My Broken Heart” by Britney Spears (1999)

Taken from Britney Spear’s debut album, …Baby One More Time, this song was originally intended for Toni Braxton, with many praising the 18-year-old Spears for delivering a song with such strong emotional content.

14. “Not Gon’ Cry” by Mary J. Blige (1995)

This tear-jerking song is one of Mary J. Blige’s most popular tunes, reaching number one on Billboard’s R&B Singles in 1995.

The song was inspired by the movie, Waiting to Exhale, which centers around a woman who is abandoned by her cheating husband.

What songs were on your break up playlist?

Emma C
Freelance Writer