50 Memorable Faces

AP Photo/Reed Saxon

50 Memorable Faces

1 of 50

Lady Gaga

Jason Merritt/Getty Images

WHEN AND WHERE The 2010 Grammy Awards
WHY WE LOVE IT For her first appearance at the Grammy Awards, Lady Gaga didn’t disappoint in an ombre yellow wig, bubblegum pink lips, and heavy metallic shadow.

Try on Lady Gaga’s statement-making hair with our Hollywood Makeover Tool!

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Nicki Minaj

Lester Cohen/WireImage

WHEN AND WHERE The 2011 Grammy Awards
WHY WE LOVE IT This day in age, firsts are almost impossible. Minaj’s leopard-spray-painted platinum bouffant was truly one-of-a-kind.

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Drew Barrymore

David Fisher/Rex USA

WHEN AND WHERE The 2009 Golden Globe Awards
WHY WE LOVE IT This whipped-up bob might have been a risk, but paired with soft makeup and a diaphanous gown, Barrymore pulled it off with aplomb.

Try on Drew Barrymore’s many hairstyles with our Hollywood Makeover Tool!

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Christina Aguilera

Jeffrey Mayer/WireImage

WHEN AND WHERE The 2001 Grammy Awards
WHY WE LOVE IT Down-to-there platinum braids were fitting for the artist, whose eponymous album went platinum a whopping nine times.

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Gwen Stefani

Jim Smeal/WireImage

WHEN AND WHERE The 1998 Grammy Awards
WHY WE LOVE IT Only the No Doubt front-woman could make a headful of loopy buns look downright sophisticated. Also note her pencil-perfect brows.

Try on Gwen Stefani’s many wild hairstyles with our HollywoodMakeover Tool!

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Paula Abdul

Jim Smeal/WireImage

WHEN AND WHERE The 1990 Grammy Awards
WHY WE LOVE IT With her hair piled on top of her head in a gold scrunchie, Abdul was straight-up pop perfection.

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Marlee Matlin

Ron Galella/WireImage

WHEN AND WHERE The 1987 Academy Awards
WHY WE LOVE IT Only in the height of the ‘80s would poufy bangs and baby’s breath fly on a Best Actress winner.

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Cher

Scott Downie/CelebrityPhoto.com

WHEN AND WHERE The 1986 Academy Awards
WHY WE LOVE IT Some people would get lost in this burst of crystals and feathers. In Cher’s case, it’s the woman that makes the headdress, not vice versa.

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Cyndi Lauper

Ron Galella/WireImage

WHEN AND WHERE The 1984 Grammy Awards
WHY WE LOVE IT Presenting at her first Grammys in no less than five shades of eyeliner, it’s no wonder Lauper would go on to have a MAC makeup collection.

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Gwyneth Paltrow

Matt Baron / BEImages

WHEN AND WHERE The 2002 Academy Awards
WHY WE LOVE IT Her sheer tank dress turned heads, but her Heidi braids and seriously smoky eyes were worth a second glance.

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Britney Spears

Kevin Mazur/WireImage

WHEN AND WHERE The 2002 Grammy Awards
WHY WE LOVE IT While she would later experiment with shorter styles, on this night her wild ringlets reached impressive lengths.

Try on Britney Spears's hair with our Hollywood Makeover Tool!

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Kate Hudson

Frank Foden/ZUMA Press

WHEN AND WHERE The 2001 Academy Awards
WHY WE LOVE IT Hudson was nominated for her role in Almost Famous, but with curls this cute she was fully on her way to the A-List.

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Jennifer Lopez

SGranitz/WireImage.com

WHEN AND WHERE The 2000 Grammy Awards
WHY WE LOVE IT While most couldn’t tear their eyes from her plunging neckline, her diffuse green shadow and lush, bumped-up ponytail were likewise statement-making.

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Hilary Swank

STEWART COOK / Rex

WHEN AND WHERE The 2000 Academy Awards
WHY WE LOVE IT Swank’s cropped Boys Don’t Cry hair-for which she won Best Actress-grew into this adorable side-swept pixie just in time for the red carpet.

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Angelina Jolie

Steve Granitz/WireImage

WHEN AND WHERE The 2000 Academy Awards
WHY WE LOVE IT Jet-black hair and nude lipstick make Angelina’s pillowy lips even more arresting. (We didn't think it was possible, either.)

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Cameron Diaz

Steve Granitz/Retna

WHEN AND WHERE The 1999 Academy Awards
WHY WE LOVE IT Adorable in a crisp barretted bob, Diaz was striking even without her signature beachy waves.

Try on Cameron Diaz’s many hairstyles with our Hollywood Makeover Tool!

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Madonna

SGranitz/WireImage

WHEN AND WHERE The 1999 Grammy Awards
WHY WE LOVE IT Ray of Light won Album of the Year; Madonna went dark with an angular brunet cut and heavy crimson lips.

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Jewel

KMazur/WireImage

WHEN AND WHERE The 1998 Grammy Awards
WHY WE LOVE IT With Pieces of You going platinum twelve times over, Jewel could do no wrong: Skinny, sectioned-off ponytails and asymmetrical face-framing pieces, included.

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Kate Winslet

Steve Granitz/WireImage

WHEN AND WHERE The 1998 Golden Globe Awards
WHY WE LOVE IT Winslet epitomized '90s glam with a piled-high updo, full lip liner, and choker necklace. Oh, and her leading role in Titanic, one of the highest grossing films of all time.

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Minnie Driver

Evan Agostini/Liaison

WHEN AND WHERE The 1998 Academy Awards
WHY WE LOVE IT Driver’s unconventional beauty -tight ringlets, snow-white skin-was a breath of fresh air.

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Celine Dion

AP Photo/Kathy Willens

WHEN AND WHERE The 1997 Grammy Awards
WHY WE LOVE IT Celine Dion nailed the ‘90s. “My Heart Will Go On”-which won Record of the Year-was the definitive lovesong; brick-red lipstick and flipped-up ends were the definitive beauty trends.

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Winona Ryder

Ron Galella/WireImage

WHEN AND WHERE The 1994 Golden Globe Awards
WHY WE LOVE IT The actress was nominated for her portrayal of the boyish Jo March in Little Women-but she dressed it up on the red carpet with a sweep of purple eye shadow and rosy lipstick.

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Elizabeth Taylor

Time Life Pictures/DMI/Time Life Pictures/Getty Images

WHEN AND WHERE The 1993 Academy Awards
WHY WE LOVE IT Only Elizabeth Taylor can successfully pair hair this big with blue eye shadow, pink lipstick and heavy rouge.

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Demi Moore

Scott Downie/CelebrityPhoto.com

WHEN AND WHERE The 1992 Academy Awards
WHY WE LOVE IT Long silky strands may be Moore’s signature, but she was coolly confident in short, swept-back waves and precise red lips.

Try on Demi Moore’s many hairstyles with our Hollywood Makeover Tool!

25 of 50

Mariah Carey

Bill Swersey/Liaison/Getty Images

WHEN AND WHERE The 1991 Grammy Awards
WHY WE LOVE IT The Best New Artist winner should also have gotten best hair with this fun spiral perm.

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Julia Roberts

Ron Wolfson/Landov

WHEN AND WHERE The 1990 Golden Globe Awards
WHY WE LOVE IT Riotous curls, a contagious smile, and natural brows? It's no wonder Julia Roberts was America's sweetheart after winning Best Supporting Actress for her role in Steel Magnolias.

Try on Julia Roberts’ hair with our Hollywood Makeover Tool!

27 of 50

Meryl Streep

Ron Galella/WireImage

WHEN AND WHERE The 1979 Academy Awards
WHY WE LOVE IT For her first of many trips to the Oscars, Streep let her soft blond hair, natural flush, and inimitable acting chops do all the talking.

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Barbra Streisand

AP Photo/George Birch

WHEN AND WHERE The 1969 Academy Awards
WHY WE LOVE IT When Streisand accepted the Best Actress award for Funny Girl her quintessentially ‘60s bumped-up bob, nude lips and cat-eye liner were no laughing matter.

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Marilyn Monroe, 1962

Michael Ochs Archives/Getty Images

The actress accepted a Golden Globe in 1962 for her performance in The Misfits in a flipped-up platinum bob, flicked-out cat-eye liner, and heavy faux lashes.

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Michelle Williams

Jason Merritt/Getty Images

WHEN AND WHERE The 2011 Academy Awards
WHY WE LOVE IT “I didn’t want her to look like a sea of white,” makeup artist Jeanine Lobell said of the pewter shadow she dusted under the star’s eyes.

Try on Michelle Williams' many hairstyles with our Hollywood Makeover Tool!

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Natalie Portman

Kevin Mazur/WireImage

WHEN AND WHERE The 2011 Academy Awards
WHY WE LOVE IT With soft waves and a mama-to-be-glow, the tortured ballerina the Best Actress winner portrayed in Black Swan couldn’t have been further from her mind.

Try on Natalie Portman’s many hairstyles with our Hollywood Makeover Tool!

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Anne Hathaway

Steve Granitz/WireImage

WHEN AND WHERE The 2011 Golden Globe Awards
WHY WE LOVE IT Hairstylist Adir Abergel countered the star’s floor-length sequined gown with this easy style. "I wanted to let her natural wave surface," he explained.

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Emma Stone

Kyle Rover/Startraksphoto.com

WHEN AND WHERE The 2010 Golden Globe Awards
WHY WE LOVE IT Stone deftly embraced her newly blond hair with a pale palette of peachy lips, pastel cheeks, and lush lashes.

Try on Emma Stone’s many hairstyles with our Hollywood Makeover Tool!

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Sandra Bullock

Jason Merritt/Getty Images

WHEN AND WHERE The 2010 Academy Awards
WHY WE LOVE IT The precision of this hairstyle is astounding. “The most important component of this look was the gently curved part, which started right above the arch of her brow,” hairstylist Adir Abergel told us.

Try on Sandra Bullock’s sleek hairstyles with our Hollywood Makeover Tool!

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Katy Perry

Gilbert Flores/CelebrityPhoto.com

WHEN AND WHERE The 2010 Grammy Awards
WHY WE LOVE IT "I have this whole India thing going on because we came back from India a few weeks ago," Perry said of her gold bindi and gilded eye shadow.

Try on Katy Perry’s many hairstyles with our Hollywood Makeover Tool!

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Jennifer Aniston

Dan MacMedan/WireImage

WHEN AND WHERE The 2009 Academy Awards
WHY WE LOVE IT The hairline braid was a super-simple tweak that elevatedAniston’s covetable sun-kissed layers.

Try on Jennifer Aniston’s many hairstyles with our Hollywood Makeover Tool!

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January Jones

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WHEN AND WHERE The 2009 Golden Globe Awards
WHY WE LOVE IT By pairing her soft, sculpted waves with a modern tangerine lip, Jones showed us the joys of retro beauty weren't just for Betty Draper.

Try on January Jones’s retro waves with our Hollywood Makeover Tool!

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Taylor Swift

Kevin Mazur/WireImage.com

WHEN AND WHERE The 2008 Grammy Awards
WHY WE LOVE IT The Best New Artist nominee was also America’s reigning sweetheart with her perfect ringlets and fairydust eye shadow.

Try on Taylor Swift’s signature curls with our Hollywood Makeover Tool!

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Sienna Miller

David Fisher/Rex USA

WHEN AND WHERE The 2007 Golden Globe Awards
WHY WE LOVE IT Who knew a coronation-style braided headband could be so fresh, inviting and appealing?

Try on Sienna Miller’s braids with our Hollywood Makeover Tool!

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Reese Witherspoon

Kevin Winter/Getty

WHEN AND WHERE The 2007 Golden Globe Awards
WHY WE LOVE IT Witherspoon's airy bangs made a huge bang on the red carpet. "I got more questions and emails about this haircut than anything I've ever done," says hairstylist Mark Townsend, who created the look.

Try on Reese Witherspoon’s many hairstyles with our HollywoodMakeover Tool!

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50 Memorable Faces

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Lady Gaga

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Nicki Minaj

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Drew Barrymore

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Christina Aguilera

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Gwen Stefani

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Paula Abdul

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Marlee Matlin

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Cher

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Cyndi Lauper

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Gwyneth Paltrow

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Britney Spears

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Kate Hudson

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Jennifer Lopez

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Hilary Swank

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Angelina Jolie

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Cameron Diaz

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Madonna

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Jewel

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Kate Winslet

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Minnie Driver

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Celine Dion

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Winona Ryder

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Elizabeth Taylor

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Demi Moore

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Mariah Carey

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Julia Roberts