1. “Nothing Compares 2 U,” Sinéad O’Connor
The one truly transcendent single to top the charts in the first year of the decade. O’Connor’s delivery is intimate and heartbreaking, the production pristine. This is one of Prince’s great triumphs as a songwriter, but he was less than gracious in his response to O’Connor’s cover: reportedly he took her to task for cursing in interviews, she told him to go fuck himself, and he tried to beat her up. Rock and roll!

2. “Ice Ice Baby,” Vanilla Ice
Not what you’d call “truly transcendent,” but too late: for the last 20+ years, the people have spoken, and Vanilla Ice has become one of the defining pop icons of the 90s—all on the basis of these four supremely silly minutes.

3. “Vogue,” Madonna
After owning the 80s, Madonna slammed the door hard with this catchy dance anthem that ended up—in classic Madonna fashion—on the soundtrack of a mediocre movie, Dick Tracy. Remember the Madonna-Warren Beatty romance? Yeah, that happened.

4. “Black Velvet,” Alannah Myles
Speaking of the 80s, did you have any idea this song was a hit in 1990 instead of, like, 1985? Yeah, neither did I. Karaoke gold 4ever.

5. “I’ll Be Your Everything,” Tommy Page
Musically, this is not a great song—but you have to give Tommy Page credit for coming up with the quintessential soundtrack to post-prom makeouts. During the sax solo, you can almost smell the peppermint schnapps.

6. “Hold On,” Wilson Phillips
Another karaoke classic, this number is being revived this year with a prominent placement in Bridesmaids. Wilson Phillips make a cameo, and Wendy is definitely still the hottest.

7. “Opposites Attract,” Paula Abdul with the Wild Pair
God bless you, Paula Abdul: never afraid to bring the ridiculous. MC Skat Kat got a solo album out of this. You know—for the kids!

8. “Escapade,” Janet Jackson
No Minnesota artist had a #1 single in 1990, but it was peripherally a big year for the Gopher State. Besides the Prince-penned “Nothing Compares,” MC Skat Kat was voiced by a pair of Minnesotans and the production duo Jimmy Jam and Terry Lewis had a huge hit with Janet Jackson’s Rhythm Nation 1814. When you hear the shout-out to Minneapolis in “Escapade,” you keep waiting to hear other cities take their turn. Nope—all the love goes to us. Psych!

9. “Another Day in Paradise,” Phil Collins
Chronologically, this was the first #1 hit of the 90s—which might have been an omen. Say what you will, but then listen to the rest of the songs on this list. You’ll find yourself longing for the subtle artistry of The Phil.

10. “Black Cat,” Janet Jackson
Nice guitar solo by—I looked it up—Dave Barry. No, not that Dave Barry, though unfortunately that guy’s in a band too.

11. “I’m Your Baby Tonight,” Whitney Houston
In retrospect, you wonder whether she was already picturing a crack vial when she sang this song.

12. “Blaze of Glory,” Jon Bon Jovi
Some part of my brain vaguely remembers this neo-Gunsmoke guitar hook from my miserable early teenage years. I’d like to have that part of my brain back now, please.

13. “She Ain’t Worth It,” Glenn Medeiros featuring Bobby Brown
You know Bobby Brown was not picturing a crack vial when he dropped this guest rap, because she is worth it. Right?

14. “(Can’t Live Without Your) Love and Affection,” Nelson
Surprisingly listenable, thanks to a catchy acoustic guitar hook. Rapunzel! Rapunzel!

15. “Step by Step,” New Kids on the Block
You know what I forgot about NKOTB? Falsetto. How ’bout that.

16. “Close to You,” Maxi Priest
On this list, this song represents the exact dividing line between “has some kind of merit that might cause you to willingly choose to listen to it ever again in your life” and “doesn’t.” I could go either way with Maxi Priest.

17. “Vision of Love,” Mariah Carey
18. “Release Me,” Wilson Phillips
19. “I Don’t Have the Heart,” James Ingram
20. “Love Takes Time,” Mariah Carey
Relatively tolerable power ballads. (Of note: these are two of four #1 singles Mariah Carey scored off a single album—her eponymous debut—a feat no female artist would match until Katy Perry in 2010-11.)

21. “Love Will Lead You Back,” Taylor Dayne
22. “It Must Have Been Love,” Roxette
23. “If Wishes Came True,” Sweet Sensation
24. “Because I Love You (The Postman Song),” Stevie B
Completely intolerable power ballads.

25. “Praying for Time,” George Michael
1990, what were you on?! Oh, right…crack.

26. “How Am I Supposed to Live Without You,” Michael Bolton
It hurts! It hurts! Make 1990 stop!

– Jay Gabler

The 1990s Project is my attempt to give the decade’s music a fair shot at disproving my offhand assessment that the 90s were the armpit of modern musical history. The project started on my Tumblr, and has now moved to The Tangential. My goal is to visit, or revisit, 100 of the decade’s most acclaimed, popular, and/or interesting albums. Here are the albums I’ve written about so far.

1. Radiohead, OK Computer (1997)
2. My Bloody Valentine, Loveless (1991)
3. The Flaming Lips, The Soft Bulletin (1999)
4. Moonshake, Eva Luna (1992)
5. Red Hot Chili Peppers, Blood Sugar Sex Magik (1991)
6. Liz Phair, Exile in Guyville (1993)
7. Erykah Badu, Baduizm (1997)
8. Neutral Milk Hotel, In the Aeroplane Over the Sea (1998)
9. Fugazi, Red Machine (1995)
10. Matthew Sweet, 100% Fun (1995)
11. Pavement, Slanted and Enchanted (1992)
12. The Bodyguard soundtrack (1992)
13. Marcy Playground, Marcy Playground (1997)
14. 10,000 Maniacs, Our Time in Eden (1992)
15. Shania Twain, Come On Over (1997)
16. Dr. Dre, The Chronic (1992)