Top Navigation

InStyle.com InStyle.com

News
Fashion
Celebrity
Beauty
Hair
Lifestyle
Shop
How To
Video
In The Mag

Search

Profile Menu

Your Account

Account

Join Now / Your Account
Newsletters this link opens in a new tab
Email Preferences this link opens in a new tab
Manage Your Subscription this link opens in a new tab
Help

More

Give a Gift Subscription this link opens in a new tab

Subscribe

Explore InStyle

InStyle.com InStyle.com

Search
Explore
Explore
- Badass Women
  
  Badass Women celebrates women who show up, speak up and get things done. Read More
- Splitting Hairs
  
  Our monthlong exploration of hair based on a survey of women across America. Read More
- Equal Pay
  
  Money is power, and women aren’t getting their share of it. The time to close that gap is now. Read More
News
Fashion
Fashion
See all Fashion
Celebrity
Celebrity
See all Celebrity
Beauty
Beauty
See all Beauty
Hair
Hair
See all Hair
Lifestyle
Lifestyle
See all Lifestyle
Shop
Shop
See all Shop
How To
How To
See all How To
- Look Your Best
Video
In The Mag

Profile Menu

Subscribe this link opens in a new tab

Your Account

Account

Join Now / Your Account
Newsletters this link opens in a new tab
Email Preferences this link opens in a new tab
Manage Your Subscription this link opens in a new tab
Help

More

Give a Gift Subscription this link opens in a new tab

Follow us

Home
Awards & Events
Red Carpet
Grammys
The Risk-Taker Awards

The Risk-Taker Awards

By InStyle.com

Jan 25, 2010 @ 12:15 pm

Alternative Sheikh Award

Gilbert Flores/Celebrity Photo

The Risk-Taker Awards

Start Slideshow

1 of 8

Facebook Twitter Email Send Text Message

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

Advertisement

Advertisement

2 of 8

Facebook Twitter Email Send Text Message

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

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

Vince Bucci/Getty Images

Eve in Jean Paul Gaultier, 2002

3 of 8

Facebook Twitter Email Send Text Message

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

Advertisement

4 of 8

Facebook Twitter Email Send Text Message

Best Liner Notes

Best Liner Notes

KMazur/WireImage, Jeff Kravitz/FilmMagic

Avril Lavigne in her own design and Converse sneakers, 2003

5 of 8

Facebook Twitter Email Send Text Message

Razor-Sharp Tailoring Award

Razor-Sharp Tailoring Award

Fitzroy Barrett/Globe Photos

Missy Elliott in Versace, 2000

6 of 8

Facebook Twitter Email Send Text Message

Most Riveting Artist

Most Riveting Artist

Jeff Vespa/IPOL/Globe Photos

Monica in D&G, 2000

Advertisement

Advertisement

Advertisement

7 of 8

Facebook Twitter Email Send Text Message

Alternative Sheikh Award

Alternative Sheikh Award

Gilbert Flores/Celebrity Photo

Alicia Keys in Christian Dior, 2002

Share the Gallery

Pinterest Facebook

Up Next

Share the Gallery

Pinterest Facebook

Advertisement

Popular in Celebrity

I Worked Out Like Jennifer Lopez, Down to Her Bedazzled Tumbler
Marc Anthony Had a Confusing Nickname for Jennifer Lopez
Constance Wu Misses the Days of Plastic Bra Straps
Salma Hayek’s American Dream
The "Recurring Argument" That Threatened John F. Kennedy Jr. and Carolyn Bessette's Relationship
Jennifer Aniston's Current Must-Haves, From Classic Levi's to an $85 Candle
Margot Robbie on Keeping Her Cool in the Spotlight
Johnny Depp Immediately Fell in Love with Vanessa Paradis's Back
Connie Britton: "Where Is Our Humanity at the Border?"
The Sad Reason Jackie Kennedy's Clothes Were Donated to a Convent After She Died
Prostitution Is on the Verge of Being Legalized — These Women Want it to Stop
Katie Couric Recalls Covering Princess Diana’s Death
The Evolution of Julia Stiles
Ashleigh Cummings Promises She's Not Being a "Diva" About Sustainability
“There Has to Be Gun Control”: Celebrities Speak Out
We Ranked Keanu Reeves's Most Memorable Romantic Lead Roles by Keanu-ness
Meet the Woman Making it Easier for Police to Put Child Predators Behind Bars
Jennifer Aniston Has Found Her Power
Sofía Vergara Just Gave Us the Best Reason to Buy New Underwear
Lance Bass on Hiding Behind Baggy Clothes Before Coming Out: “I Just Wanted to Disappear”

All Topics in Celebrity

Celebrity

Everything in This Slideshow

Advertisement

View all gallery

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

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

Best Diane Keaton as Ozzy Osbourne Impersonation Award

Best Liner Notes

Razor-Sharp Tailoring Award

Most Riveting Artist

Alternative Sheikh Award

Share options

Facebook Twitter Email Send Text Message

Magazines & More

Learn More

Subscribe this link opens in a new tab
Contact Us
Advertise
Sitemap

Connect

Follow Us

Subscribe to Our Newsletter

Other Meredith Sites

Other Meredith Sites

Allrecipes this link opens in a new tab
All People Quilt this link opens in a new tab
Better Homes & Gardens this link opens in a new tab
Coastal Living this link opens in a new tab
Cooking Light this link opens in a new tab
Diabetic Living this link opens in a new tab
EatingWell this link opens in a new tab
Eat This, Not That this link opens in a new tab
Entertainment Weekly this link opens in a new tab
Extra Crispy this link opens in a new tab
Family Circle this link opens in a new tab
Fitness Magazine this link opens in a new tab
Fit Pregnancy this link opens in a new tab
Food & Wine this link opens in a new tab
Health this link opens in a new tab
Hello Giggles this link opens in a new tab
Kraft Recipes this link opens in a new tab
Martha Stewart this link opens in a new tab
Midwest Living this link opens in a new tab
Martha Stewart Weddings this link opens in a new tab
More this link opens in a new tab
Myrecipes this link opens in a new tab
Mywedding this link opens in a new tab
Parents this link opens in a new tab
Parenting this link opens in a new tab
People this link opens in a new tab
People en Español this link opens in a new tab
Rachael Ray Magazine this link opens in a new tab
Real Simple this link opens in a new tab
Shape this link opens in a new tab
Ser Padres this link opens in a new tab
Siempre Mujer this link opens in a new tab
Southern Living this link opens in a new tab
Traditional Home this link opens in a new tab
Travel & Leisure this link opens in a new tab

InStyle is part of the Meredith Beauty Group. © Copyright 2019 Meredith Corporation. All Rights Reserved. InStyle may receive compensation for some links to products and services on this website. Offers may be subject to change without notice. Privacy Policythis link opens in a new tab | Terms of Servicethis link opens in a new tab | Ad Choicesthis link opens in a new tab | Your California Privacy Rightsthis link opens in a new tab | EU Data Subject Requeststhis link opens in a new tab

View image

The Risk-Taker Awards

this link is to an external site that may or may not meet accessibility guidelines.