Britney Spears (2002)
No, Ma’am! Not a girl, not yet a streetwalker. It’s hard to imagine this leather-clad cutie with kids, isn’t it?
Moonman In 1991, the Purple One showed us a different side of himself when he performed his hit ”Gett Off” wearing yellow laser-cut lace and peekaboo pants.
Lil' Kim (1999)
Breast in Show Before her year in prison for lying under oath, the pint-sized rapper wore this technically street-legal unitard to the ceremony. Hooray for pasties!
Marilyn Manson and Rose McGowan (1998)
Chained Melody The draped beading that Rose McGowan (with then-fiancé Marilyn Manson at the 1998 awards) called a ”gown” made for a better window than a door; we’ve seen less skin on late-night Cinemax
Destiny's Child (2001)
Pow-wow Ow! Cruise-ship act or internationally renowned pop trio? It was hard to tell when Destiny’s Child appeared on the red carpet wearing matching, egregiously fugly coral-and-turquoise ensembles.
Axl Rose (2002)
Rose’s Thorns Upon his triumphant return to the stage in 2002, the nearly unrecognizable Guns N’ Roses frontman sported shades, braids, and a football jersey, the snake-hipped hesher of yesteryear but a distant memory.
Christina Aguilera (2003)
Pink Lemon Either Christina Aguilera was shying away from her previously too-revealing looks by wearing feathered magenta couture, or she was barfed on by a technicolor flamingo — tough call.
Paula Abdul (1987)
Two Steps Back Oh, Paula. You should have known better than to take wardrobe advice from MC Skat Kat
Macy Gray (2001)
Fashion Statement Sure, this ensemble may appear to have an expiration date, but a quick trip to the hardware store for duct tape can extend its shelf life indefinitely.
Tommy Lee (1999)
J. Crüe Lee shows Christina Aguilera that just the right blend of dirty and pervy can make the flasher look red-carpet-ready.
Lenny Kravitz (1993)
Hi-Ho Silver Just because the award is a spaceman doesn’t mean you have to dress like one, Mr. Kravitz.
Busta Rhymes (1997)
Pattern Boldness Although making a dress out of curtains worked for Maria Von Trapp, on Busta it is definitely not a good thing. (Yes, that’s Martha Stewart with him!)
Lil Mama (2007)
Child’s Play Little Bo Peep has lost her sheep — and, apparently, her mind — in this oddly infantilizing purple satin onesie. And the pacifier? We have no words.
Jennifer Lopez (2009)
Choke Hold Things were going pretty swell for J.Lo and her short ‘n sweet mini…until the Attack of the Velvet Anaconda and its Biscuit-Colored Sleeves of Doom.
Amber Rose (2009)
Nothing To Hide No idea where she put her keys and lipstick, but in this demure snakeskin bodysleeve, Kanye’s then-paramour brought VMAs fashion to its knees — and struck fear in the heart of spandex pythons everywhere.