1. Sinead O’Connor “Nothing Compares 2 U” (1990)
Sinead O’Connor’s heart wrenching ballad “Nothing Compares 2 U” was probably the first breakup song you ever heard, thanks to your older siblings (or friends’ siblings) blasting it in their room after their first broken heart. When your first relationship came crumbling down a few years later, the song gained a whole new meaning. And don’t even get us started on that tear in the video.
2. Boyz II Men, “The End of the Road” (1992)
Boyz II Men’s classic “End of the Road” remained a staple on the junior high and early high school breakup scene long after its ’92 release. Warning: listening to it will bring you right back to the gym for those awkward grade eight dances.
3. Guns N Roses, “November Rain” (1992)
Ah, “November Rain.” Basically, this was a breakup rite of passage. Slash soloing outside the church? Enough said.
4. Lisa Loeb, “Stay” (1994)
This one hit wonder will never fail to transport you back in time – both to when Reality Bites was your favourite film (it’s on the soundtrack) and to when your over-dramatic junior high self would play it on your Walkman post-breakup.
5. Alanis Morissette, “You Oughta Know” (1995)
Although every song from Jagged Little Pill holds a special place in the hearts of most young professionals, nothing felt quite as liberating as a female than belting out “You Oughta Know” with your girlfriends after your “boyfriend” of a month left you for the “older version” of you (who didn’t have braces).
6. Green Day, “Good Riddance (Time of your Life)” (1997)
An open mic favourite to this day, this Green Day classic is about a general reflection and appreciation for life’s experiences. It’s the kind of song that reflects a mature, amicably ending relationship that “was worth all the while,” but needed to come to an end – you know, because you were going to different universities.
7. Brian McKnight, “6, 8, 12” (1999)
We’re going to bet that more than a few of you listened to this song via your Discman on the solo walk home from high school in the months after you and your high school sweetheart parted ways on a dramatic, hand-written letter-filled breakup. And yeah, you probably tried not to cry each time.
8. Macy Gray, “I Try” (2000)
Another famous high school breakup ballad (well, post-breakup ballad) is Macy Gray’s “I Try”. You could totally relate to exactly what Gray was talking about in this song when you’d “play it off” when you ran into your ex in the halls, but were later “dreaming” of them in your poster-filled bedroom. Right?
9. Coldplay, “The Scientist” (2002)
This Coldplay favourite pretty much encapsulates everything that runs through your head after you realize that the breakup was a horrible mistake, and that all you want is to take it “back to the start.” And in the wake of a breakup, you can never just play it once.
10. Britney Spears, “Everytime” (2003)
Even if you were the only one in your grade who didn’t jump on the Britney Spears bandwagon, it was difficult not to feel sorry for poor Britney when you heard “Everytime.” It was even harder not to feel sorry for yourself when it made you cry when it came on the radio the week after you were dumped.
11. Usher, “Burn” (2004)
Usher’s “Burn” did indeed burn us all a little more than the rest. Why? We were all a little older and more mature by the time it came out, and the real, raw, truthful lyrics depict a much deeper relationship than your typical high school partnership.
12. The Killers, “Mr. Brightside” (2004)
The Killers’ “Mr. Brightside” gives the guys a chance to vent. The song is apparently about catching a cheating partner. Even if she didn’t cheat on you, when thoughts of what she may be doing post-breakup invaded your suddenly jealous mind, this song was there to play in your car.
13. Beyoncé, “Irreplaceable” (2006)
Queen B empowered countless young women with “Irreplaceable.” Any female who had to deal with a total d-bag proudly played this song on repeat when it came out – likely while on the treadmill and looking better than ever. There were no tears during this song.
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