The MTV Video Music Awards are essentially the only ceremony left where you’re mocked for not looking ridiculous. Mariah Carey’s tasteful, chocolate covered gown at the ’98 VMAs? Elton John’s blue suit for his performance with Guns ’N Roses in ’92? Shamefully tasteful. Here are 10 stars who weren’t afraid to chill us at the VMAs.
10. Cher, 2010: Turning Back Time For The Hell Of It
You can just picture the conversation that led to Cher’s “If I Could Turn Back Time” moment at the 2010 VMAs. A producer prodded her and prodded her and Cher threw up her arms and muttered, “OK, whatever, I’ll do it. Whatever.” Thank God she did. The woman Mackie’d out, and we’re all the richer for it.
9. Whitney Houston, 2000: Fabulous, Yet Ridiculous
I forget sometimes that in 2000, we were living in a very “Love Don’t Cost a Thing” world where even Whitney Houston felt obligated to wear gaudy furs, bare midriffs, and shiny-ass jeans. I’ll never forgive you, J-Lo, but at least Whitney pulled off a certain amount of kickass flair here. (By the way, Jennifer Lopez looks boringly tacky at EVERY VMAs, for your information.)
8. Missy Elliott, 1997: Supa Dupa Trashbag Pupa
God, I love classic Missy Elliott. She scooped up Video of the Year for “Work It” in ’02, but it’s hard not to cherish her Hefty Bag heyday from ’97 ceremony. M.I.A. tried to achieve this glamor in later years, but only Missy was (literal) trash with class.
7. Lady Gaga, 2009: Where The Wild Things Are? Under That Mask?
As Eminem calcified into a plastic-surgerized Lego man behind her, Lady Gaga took the stage wearing this shocking, very vermilion lace situation that concealed her face. She only wore 45 other outfits the same evening, but I assure you this was the most insane of the bunch.
6. Madonna: Shanti Ash-Tacky
To me, this is one of Madonna’s most glorious moments, a totally unexpected Aztec/Fairuza Balk moment that will never, ever be duplicated. She ran off with Video of the Year that ceremony for “Ray of Light,” and I hope she pumped that Moonman like a barbell for years thereafter.
5. Gwen Stefani, 1998: Orange County Goes Blue Raspberry
It’s easy to forget that before Gwen Stefani was the glamorized, uber-platinum fashionista of the 2000s, she was mostly just ridiculous-looking. Here, she resembles a blue Icee outfitted by Frederick’s of Hollywood.
4. Paula Abdul, 1991: Eye-Searing Vibeology
This might be the most famously terrible VMA outfit ever, but I give Paula Abdul credit for wearing an entire Tiffany diamond mine on her torso. Never forget that in 1991, Paula Abdul was basically just Tatiana Ali in showgirl underwear.
3. Michael Jackson, 2002: Strike Up The Bandleader
Yes, this is a relatively demurer look for the King, but I’m sorry: That is Christmas paraphernalia blinging all across his velvet blazer. That is Jennifer Connelly’s hair. That is a golden garland adorning his arm. Below frame, he’s wearing those gilded shinguards, making everyone on Manchester United gold with envy.
2. Christina Aguilera, 2001: Janky In A Bottle
Christina Aguilera always forgets that she is not R&B/hip-hop in any way. It never works out for her, with the possible exception of the “Dirrty” video. You know your outfit is a problem when Lil Kim looks 25 times more restrained next to you.
1. Prince, 1999: Little Blue Coquette
Now, Prince had actually dressed more outrageously than this at the VMAs. Surely you remember his assless yellow ensemble from the ceremony where he performed “Gett Off,” but that was at least provocative. In 1999, Prince showed up to introduce performers TLC, and he did so wearing this… this… ill-fitting blue pleather contraption and cornrows like a 12-year-old girl. I remember seeing this when it first aired and wondering why he looked like Coolio’s intergalactic niece. I’m still wondering, guys.