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

Kathryn Newton Is the Breakout Star of<em> Big Little Lies </em>— and She’s Just Getting Started
What Is Colin Jost's Net Worth?
Meet the Former Olympic Soccer Player Who Made History Calling the Men's World Cup
Alan Alda on Longevity and Cynical Optimism
Jonathan Van Ness Always Asks Himself This One Question Before Making a Purchase
Taylor Swift Finally Got Political — Why Isn’t It Enough?
What Is Scarlett Johansson's Net Worth?
Meet Sylvia Earle, the Jane Goodall of the Sea
Here's the Story of How I Became "Awkwafina"
Actress and Cabaret Star Ute Lemper Reminisces Over Her 30-Year Career
Of Course Lori Loughlin Is a Leo
Hundreds of Instagram Accounts Have Been Shut Down Over Photos Like This
Nancy Pelosi and Sarah Huckabee Sanders Both Wore Pink Today, but the Similarities End There
What Does the Rainbow Flag Actually Stand For?
Lady Gaga’s Infamous Meat Dress Has a New Home in Las Vegas
Cate Blanchett Loves the Smell of Newborn Babies
How Priyanka Chopra Jonas Will Change the World
Lucy Boynton and Sabrina Carpenter Agree: Do Not Look at Pics of Your Old Outfits
Cecile Richards Is Not Afraid
Celebrities Are Boycotting Georgia — But Will That Help?

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

Updated: Jan 26, 2010 @ 2:26 pm

Alternative Sheikh Award

The Risk-Taker Awards

Start Slideshow

1 of 8

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

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

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

Best Liner Notes

Best Liner Notes

KMazur/WireImage, Jeff Kravitz/FilmMagic

Avril Lavigne in her own design and Converse sneakers, 2003

5 of 8

Razor-Sharp Tailoring Award

Razor-Sharp Tailoring Award

Fitzroy Barrett/Globe Photos

Missy Elliott in Versace, 2000

6 of 8

Most Riveting Artist

Most Riveting Artist

Jeff Vespa/IPOL/Globe Photos

Monica in D&G, 2000

Advertisement

Advertisement

Advertisement

7 of 8

Alternative Sheikh Award

Alternative Sheikh Award

Gilbert Flores/Celebrity Photo

Alicia Keys in Christian Dior, 2002

Share the Gallery

Pinterest Facebook

Up Next

By InStyle.com

Share the Gallery

Pinterest Facebook

Advertisement

Popular in Celebrity

Kathryn Newton Is the Breakout Star of Big Little Lies — and She’s Just Getting Started
What Is Colin Jost's Net Worth?
Meet the Former Olympic Soccer Player Who Made History Calling the Men's World Cup
Alan Alda on Longevity and Cynical Optimism
Jonathan Van Ness Always Asks Himself This One Question Before Making a Purchase
Taylor Swift Finally Got Political — Why Isn’t It Enough?
What Is Scarlett Johansson's Net Worth?
Meet Sylvia Earle, the Jane Goodall of the Sea
Here's the Story of How I Became "Awkwafina"
Actress and Cabaret Star Ute Lemper Reminisces Over Her 30-Year Career
Of Course Lori Loughlin Is a Leo
Hundreds of Instagram Accounts Have Been Shut Down Over Photos Like This
Nancy Pelosi and Sarah Huckabee Sanders Both Wore Pink Today, but the Similarities End There
What Does the Rainbow Flag Actually Stand For?
Lady Gaga’s Infamous Meat Dress Has a New Home in Las Vegas
Cate Blanchett Loves the Smell of Newborn Babies
How Priyanka Chopra Jonas Will Change the World
Lucy Boynton and Sabrina Carpenter Agree: Do Not Look at Pics of Your Old Outfits
Cecile Richards Is Not Afraid
Celebrities Are Boycotting Georgia — But Will That Help?

All Topics in Celebrity

Celebrity
Grammys
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

Pinterest Facebook Twitter Email Print 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.