-By Frank Donovan
Valentine’s Day is a double-edged sword. If you’re happily shacked up (or happily single), you can just skip this and have a great day.
But if you’re trying to get out of that toxic relationship before the 14th, or you’re already deep in the depths of a hellish split, or even if your broken heart is left unhealed by time, we’ve assembled 20 breakup songs that run the gamut—all deep cuts from the ’90s vaults.
Whether you want to wallow with Mariah Carey or get back on the dance floor with Mark Morrison, we’ve got what the heart doctor ordered. So sit down, relax, and keep a box of tissues handy.
“Never Ever,” by All Saints (1997)
These four ladies used their voluminous cargo pants to wipe their post-breakup tears.
“Your Woman,” by White Town (1997)
Jyoti Mishra says he was reading Andrea Dworkin and Wilhelm Reich around the time he wrote this one-hit wonder for his one-man band White Town. He even did a handy FAQ about the song on his site.
Bonus points for the phrase “cut the crap.”
“Stay (I Missed You), by Lisa Loeb (1994)
It doesn’t get much more ’90s than the Reality Bites soundtrack and an Ethan Hawke-directed music video. With this song, Lisa became the first U.S. artist to reach number one on the Billboard top 100 charts before being signed.
“Again,” by Janet Jackson (1993)
Beware: You may need tissues at 2:38.
“Don’t Turn Around,” by Ace of Base (1994)
Bet you didn’t know this was originally a Tina Turner B-side!
“Caught Out There,” by Kelis (1999)
Have mercy on the man who dares cheat on Kelis.
“Special,” by Garbage (1998)
I have run you down into the ground/Spread disease about you over town
“Ex-Factor,” by Lauryn Hill (1998)
This tear-jerker was reportedly written about fellow Fugees member Wyclef Jean.
“Sleep to Dream,” by Fiona Apple (1997)
Some positively scathing reviews of an ex by Fiona Apple. She won MTV VMA for Best New Artist in a Video with the song, and gave the famous “this world is bullshit” speech.
“Un-Break My Heart,” by Toni Braxton (1996)
Toni lightens the mood of this bummer ballad at 1:54 (she plays Twister with Tyson Beckford).
“From the Bottom of My Broken Heart,” by Britney Spears (1999)
Britney filled the Abercrombie model-shaped hole in her heart with a fuzzy kangol hat, duster cardigan, and flares.
“Return of the Mack,” by Mark Morrison (1996)
The official soundtrack to dusting yourself off after a breakup and getting back on the dance floor
“My Lovin’ (You’re Never Gonna Get It) by En Vogue (1992)
When an unwelcome ex knocks at your door for a second chance, blast this from your boombox and wave your finger “no.”
“Insensitive,” by Jann Arden (1994)
When he’s just not that into you :/
“Real Love,” by Mary J. Blige (1992)
Mary’s on to the next, and this song is the want ad for Mr. Right.
“Understanding,” by Xscape (1993)
There’s some sage advice from the ladies of Xscape on good communication in here.
“Nobody Knows,” by The Tony Rich Project (1996)
For your Adult Contemporary breakups
“My All,” by Mariah Carey (1997)
Lord knows we had our pick of Mariah’s breakup songs, but this one is by far the most devastating.
“When Can I See You,” by Babyface (1994)
If only your ex would serenade you with these words instead of texting them 🙁
“Set Adrift on Memory Bliss,” by P.M. Dawn (1991)
You might reminisce about old flames, but they must stay deep in the corners of your mind where they belong, says P.M. Dawn.