The Risk-Taker Awards

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1 of 8

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

Eric Charbonneau/Berliner Studio

Jennifer Lopez in Versace, 2000

2 of 8

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

Vince Bucci/Getty Images

Eve in Jean Paul Gaultier, 2002

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Best Diane Keaton as Ozzy Osbourne Impersonation Award

Steve Granitz/Wireimage.com

Sheryl Crow in Anton pants, 2000

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Best Liner Notes

KMazur/WireImage, Jeff Kravitz/FilmMagic

Avril Lavigne in her own design and Converse sneakers, 2003

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Razor-Sharp Tailoring Award

Fitzroy Barrett/Globe Photos

Missy Elliott in Versace, 2000

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Most Riveting Artist

Jeff Vespa/IPOL/Globe Photos

Monica in D&G, 2000

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Alternative Sheikh Award

Gilbert Flores/Celebrity Photo

Alicia Keys in Christian Dior, 2002

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The Risk-Taker Awards

1 of 8

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

2 of 8

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

3 of 8

Best Diane Keaton as Ozzy Osbourne Impersonation Award

4 of 8

Best Liner Notes

5 of 8

Razor-Sharp Tailoring Award

6 of 8

Most Riveting Artist

7 of 8

Alternative Sheikh Award

Up Next

Everything In This Slideshow

The Risk-Taker Awards

1 of 8

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

2 of 8

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

3 of 8

Best Diane Keaton as Ozzy Osbourne Impersonation Award

4 of 8

Best Liner Notes

5 of 8

Razor-Sharp Tailoring Award

6 of 8

Most Riveting Artist

7 of 8

Alternative Sheikh Award

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