Paris Hilton 2009

And finally, in August of 2006, Paris Hilton released a debut album that against all odds actually managed to have a hit single, the inexplicably titled “Stars Are Blind.” Almost three years later, Paris Hilton walked the red carpet at the 2009 Grammy Awards having forgotten a pair of pants.

M.I.A. 2009

At the 2009 awards, a nine months pregnant M.I.A. showed up on her due date wearing a blue and teal patterned, multi-tiered mini-dress that both embraced and accentuated her full-bodied shape. Even better, for her onstage performance with T.I., Jay-Z, Lil' Wayne, and Kanye West, the rapper changed into a show-stoppingly sheer polka-dot ensemble that left very little to the imagination.

OK Go 2007

Long before Lady Gaga donned a blood red and be-masked outfit for the 2009 VMAs, pop group OK Go made their Grammy debut in matching red patterned suits—complete with scarlet face masks and coordinating hats. One band member stopped to explain their alien-looking costumes: "We're dressed in the future – the future dressed us."

Gwen Stefani 2006

Gwen Stefani single-handedly made maternity wear rock-chic at the 2006 Grammys in a flowing leopard-print, ombre, one-shoulder gown from her own label, L.A.M.B.

Toni Braxton 2001

Fortunately for Christina, 2001 was the same year Toni Braxton was nominated for Best Female R&B Performance and Best R&B Album, either of which might explain why she decided to wear two long strips of white fabric tethered together by a tenuous-looking elastic band.

Christina Aguilera 2001

Exactly one year after winning "Best New Artist" for the pop-princess stylings of her self-titled debut album, Christina Aguilera got dirrty in a navel-baring dress that was as eye-catching as it was jaw-dropping. Accessorized with a head full of multi-colored braids, Christina later chalked the whole look up as "an experiment."

Jennifer Lopez 2000

In what will likely go down in the annals of red carpet fashion history as the dress that started it all (see: Christina Aguilera and Toni Braxton, 2001), Jennifer Lopez’s tropical-print trappings took the fashion world by storm. Designed by Versace and paired with the briefest of blue briefs, the dress plunged down-to-there and right back up again—not unlike the eyeballs of everyone watching the 2000 Grammy awards.

TLC 1996

Before Destiny’s Child, the music world’s most successful girl group was TLC — an R&B trio made up of Rozonda "Chilli" Thomas, Lisa "Left Eye" Lopes and Tionne "T-Boz" Watkins. Staying in theme with their nominated album, the ladies went Crazy Sexy Cool for the 1996 Grammy red carpet by wearing coordinating all-white outfits. By way of explanation, their stylist told People magazine, "The Grammys are the most prestigious music event, and white is the richest color." Not so coincidentally, the group had filed for bankruptcy less than one year prior.

Mariah Carey 1991
In 1991, a fresh-faced and curly-haired Mariah Carey picked up her first two Grammy Awards while wearing a diamond-detailed and form-fitting little black dress. It was only the beginning for this ballad-belting songstress who would go on to win 19 more Grammys in her as-yet-unfinished and storied career.