Trent Reznor of NIN.

The materialistic excesses of the 80s led to a stripped-down lifestyle reboot. In the 90s you could sport long unkempt locks, avoid bathing for days, pick up a crumpled flannel shirt off your bedroom floor, go out and fit right in.

For the most part macho posturing was considered passé so even art school beta boys got female attention. Status symbols were considered ostentatious so poor guys had a chance with chicks that bought into the image-doesn’t-matter credo.

Butt-hurt Musicians wrote breakup tunes that either verbally thrashed their ex (particularly female songwriters), or were depressing, auditory pity parties. There was very little in between.

20. You Oughta Know, by Alanis Morissette

It’s the anthem of the try-hard, empowered woman of the 90s. Rumor has it the lyrics are about actor Dave Coulier of ‘Full House’, who Morissette dated when she was 16 and he was 31.

19. Ex Girl to Next Girl, by Gang Starr

Emcee Guru made the mistake of falling for a “scheming hoe.” He moved on after finding out she was in it for the Benjamins. Instead of exiting with grace, she made “crazy calls.”

18. Piss Up A Rope, by Ween

Dean Ween’s been packing her bags for the last six months and the bitch still won’t take the hint. When you’ve lost all hope, it’s time to not-so subtly tell her to bolt, perhaps for good.

17. End of the Road, by Boyz II Men

Perhaps the ultimate R&B slow jam. It doesn’t feel right to let go just yet. “It’s unnatural.”

16. Shitlist, by L7

To most a shit list is a figurative thing. For Donita Sparks it’s quite literally about grabbing a pen and violently scribbling names on a notepad. “You’ve made my shitlist.”

15. Soma, by Smashing Pumpkins

Vocalist Billy Corgan and his girlfriend, Christine Fabine, had just broken up (they later married and then got divorced). He describes the cognitive dissonance he felt after betraying himself by crawling back to her. This time around, he yearns to sing her to sleep.

14. One Week, by the Bare Naked Ladies

You’ve had a petty argument with the misses. She’s furious, yet you’re having a tough time taking her seriously. “I’m the kind of guy who laughs at a funeral.”

13. Take A Bow, by Madonna

It turned out his love was nothing more than a masquerade. Madonna found one hell of an actor, but a poor life partner.

12. All Apologies, by Nirvana

Again, you’re stuck apologizing for being the person you are. It’s become a meaningless routine, enforced by someone that can’t accept your quirks.

11. Until I Fall Away, by Gin Blossoms

You’re all alone, exploring your identity, and having some cryptic thoughts. Don’t fall into a black hole in the process.

10. I Can’t Make You Love Me, by Bonnie Raitt

Your love interest may be going through the motions. If you’ve given it your all and he or she still isn’t reciprocating the same level of love, don’t assume it’s a problem you can fix.

9. Black, by Pearl Jam

A raw, honest expression of excruciating pain and longing that anyone who’s ever lost their greatest love can relate to.

8. Ordinary World, by Duran Duran

The loss of a loved one has made the singer’s world less magic. He must come to grips with a new reality that is dull, and “ordinary.”

7. One, by U2

Bono has said this is “about relationships.” It was written during a time of possible breakup for the band. The latter particularly makes sense of the line “we’re one, but we’re not the same.”

6. Hurt, by Nine Inch Nails

Always the final song at NIN concerts, as it is frontman Trent Reznor’s favorite. He considers it to be the most personal song he’s ever written.

5. Song for the Dumped, by Ben Folds Five

Choosing this over ‘Brick’ by the same band was a tough call. Ultimately the explosive energy and cutting soundbites in this jam won out.

4. Loser, by Beck

So she’s trash talking behind your back. Just embrace the insults. Oh, and in case you’re wondering, “soy un perdidor” literally means “I’m a loser” in Spanish.

3. Nothing Compares 2 U, by Sinead O’Connor

Prince was expecting a backup singer. What he got was an once-in-a-lifetime lead vocal track from Sinead O’Connor. Sometimes it pays to show up at the studio late.

2. Don’t Go Away, by Oasis

Liam confessed he couldn’t record this song at first, because it was making him cry. Written by brother Noel, allegedly after he heard his mother was hospitalized for cancer; which later proved to not be the case.

1. Last Goodbye, by Jeff Buckley

Some people say this song was an omen as Buckley died by drowning a few years after its release.