The Risk-Taker Awards

Alternative Sheikh Award
Photo: Gilbert Flores/Celebrity Photo

The Risk-Taker Awards

01 of 07

Most Notorious Grammy (or Any Red Carpet) Dress Ever Award

Most Notorious Grammy (or Any Red Carpet) Dress Ever Award
Eric Charbonneau/Berliner Studio

Jennifer Lopez in Versace, 2000

02 of 07

All Bases Covered Award (Long? Short? Both!)

All Bases Covered Award (Long? Short? Both!)
Vince Bucci/Getty Images

Eve in Jean Paul Gaultier, 2002

03 of 07

Best Diane Keaton as Ozzy Osbourne Impersonation Award

Best Diane Keaton as Ozzy Osbourne Impersonation Award
Steve Granitz/Wireimage.com

Sheryl Crow in Anton pants, 2000

04 of 07

Best Liner Notes

Best Liner Notes
KMazur/WireImage, Jeff Kravitz/FilmMagic

Avril Lavigne

in her own design and Converse sneakers, 2003

05 of 07

Razor-Sharp Tailoring Award

Razor-Sharp Tailoring Award
Fitzroy Barrett/Globe Photos

Missy Elliott

in Versace, 2000

06 of 07

Most Riveting Artist

Most Riveting Artist
Jeff Vespa/IPOL/Globe Photos

Monica

in D&G, 2000

07 of 07

Alternative Sheikh Award

Alternative Sheikh Award
Gilbert Flores/Celebrity Photo

Alicia Keys in Christian Dior, 2002

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