Throwback Thursday: 90s Mixtape for Valentine’s Day

In case you’ve missed the overly saccharine heart and candy displays in stores or the commercials pressuring you into spending exorbitant amounts of money on jewelry, Valentine’s Day is on Sunday. While some of us are bracing ourselves for the onslaught of unnecessarily public declarations of love on social media, others are wading through post after post about “Singles’ Awareness Day” or hatred of over-commercialization/the lack of a relationship.


I thought about offering up some of the best love songs of the 90s but let’s be honest, it’s much more fun to make a breakup mix. Think of every romantic comedy you’ve ever seen: the interesting parts are the conflicts and roadblocks that keeps true love apart. The “happily ever after” is a brief montage at the end, if that. And so, with that in mind, here is my mixtape of 90s breakup songs for you to enjoy long after your Tinder hookup has left and you’re elbow deep in a pint of ice cream.

If you’re happy and in love . . . you should probably go read something else. These songs are not for you.

“Black” – Pearl Jam (1991)

If your broken heart had a voice, it would sound like Eddie Vedder.


“Song for the Dumped” – Ben Folds Five (1997)

Don’t let the upbeat sound of this song for you–this is basically the precursor for Rihanna’s “Bitch Better Have My Money.” 


“Don’t Speak” – No Doubt (1996)

This song was about the real life breakup between bandmates Gwen Stefani and Tony Kanal. The fact that they continually performed this song together is actually much less awkward than when Gwen Stefani sang her latest single on The Voice about her divorce from Gavin Rossdale to her new boyfriend, Blake Shelton, while wearing a wedding dress. Hella awkward–awkward enough for me to justify using the word “hella.”


“Nothing Compares 2 U” – Sinead O’Connor (1990)

Originally written by Prince for one of his side projects, a funk band called The Family, it was a pretty much unacknowledged song until Sinead O’Connor’s rendition. The video with close ups on O’Connor’s face has become extremely recognizable and in 1990, it won Video of the Year award at the MTV VMAs, making O’Connor the first female artist to win that particular honor. This song has maintained popularity over the last 26 years and is best listened to while staring at a photo of your ex with a lone tear running down your cheek.

I once heard a rumor that Prince considered giving this song to Carmen Electra. I don’t know if that’s true or not, but can we all just take a moment to reflect on how awful that might have been?


“I Can’t Make You Love Me” – Bonnie Raitt (1991)

Bonnie Raitt probably could have used a copy of He’s Just Not That Into You. According to Wikipedia, this song was inspired by a news story of a guy who got drunk and shot at his girlfriend’s car. Later, when a judge asked him if he’d learned anything, the guy said, “I learned, Your Honor, that you can’t make a woman love you if she don’t.”

A lesson for everyone: shooting at someone’s car will not guarantee you a date with anybody but the local sheriff.


“I Will Always Love You” – Whitney Houston (1992)

Before becoming every drunk girl’s favorite karaoke jam, this song was originally written and performed by Dolly Parton before Whitney Houston recorded a version of it for The Bodyguard. It’s by far her most popular song ever and many critics have referred to it as her signature song. I’m honestly not sure what else to say about it because if you’ve heard it, you know how beautiful this loved-and-lost song is and if you haven’t heard it, I’m sorry that you’ve spent the last thirty years in a doomsday bunker.


“Stay (I Miss You)” – Lisa Loeb (1994)

This song is best listened to on a loop while you cry to your cat and watch Reality Bites.


“Un-Break My Heart” – Toni Braxton (1996)

Although the song sounds like a regular breakup, the music video features Toni Braxton mourning over the death of her dead lover, played by Tyson Beckford. I mean, I suppose a dead partner is a good reason to dislike Valentine’s Day but it just got a little more real in this post than I intended.


“Sleep to Dream” – Fiona Apple (1997)

If you’re listening to this on Valentine’s Day, someone has pissed you off. Not enough to key their car, but you’re going to write some angry poetry about your ex and his stupid new girlfriend in your journal when you can’t sleep at 3am (theoretically me in college).


“Ex-Factor” – Lauryn Hill (1998)

Supposedly written about Wyclef Jean, this song is ideal to listen to while you lie on your bedroom floor and cry. Who understands your pain? Lauryn understands your pain.


“You Oughta Know” – Alanis Morisette (1995)

You didn’t think I could get through a whole list of breakup songs without mentioning this one, do you? This is the ultimate angry girl anthem after a breakup and if you are listening to this song on Valentine’s Day, you are mad. You are also undoubtedly singing the chorus at the top of your lungs because Alanis is the only one who gets how pissed off you are. Your ex totally screwed you over just like Dave Coulier did to her.

Even Bob Saget thinks the song
is about Coulier.

Alanis Morisette has never actually confirmed that this song was about Uncle Joey but we know. WE KNOW.

And you know what you did, DAVE.
And you know what you did, DAVE.

Fun fact, the instrumental part of this song was created by Dave Navarro and Flea after they listened to the unaccompanied vocals.

I should probably let other people decide
if my facts are fun.

Happy Valentine’s Day!

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