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In 1987, five years after starring as little Gertie in E.T., Drew appeared at a People's Choice Awards afterparty sporting full, untouched brows and a half-up, half-down hairstyle "Josie Grossie" might've favored.
At a 1991 premiere, Drew went for a tousled auburn 'do and a slick of red lipstick.
In 1995, Drew chopped off those long locks and adopted a piecy, punky hairstyle—with penciled-in brows, mauve lips and beaded chokers to match.
Showing off her darker side at 1996's Beautiful Girls premiere.
A curly girl (with bleached brows!) at the 1998 L.A. premiere of her film Ever After. Which, for the record, is like the best movie ever.
Proof positive that "Flower" wasn't an arbitrary choice of name for Drew's new beauty collection. At the '98 Academy Awards, the actress framed her face with pretty daisies, a look she'd go on to replicate at several later red carpet events.
At the 1999 Kids Choice Awards, Drew embraced her inner flower child a bit less literally, pairing a sparkly scarf with a beaded circlet and matching seafoam eyeshadow.
In Charlie's Angels, Tom Green's character refers to Drew Barrymore's as "Starfish"—so it seemed appropriate that the actress turned up at the movie's L.A. premiere with a giant sparkly starfish adorning her brunette bob.
At the same flick's London premiere, Drew edged her eyes with teal liner, pulled her hair into a tousled topknot and finished the look with a berry lip.
In 2001, the movie star set off her flawless complexion with a rosy lip at the Donnie Darko premiere.
For the premiere of Charlie's Angels: Full Throttle, Drew experimented with bleached-blonde waves and artfully-smudged black eyeliner.
Going dark and dramatic at the 2005 Oscars.

At the 2006 Met Gala, Drew stuck with simple upswept hair, shimmery highlighter and a classic red lip.


At the 2007 Los Angeles premiere of her movie Music and Lyrics, Drew pulled her hair back into a center-parted, voluminous chignon, which she framed with a pair of gold statement hoops. So glamorous.
Drew went for yet another daring chop in 2009, lopping multiple inches off for a chin-length bob and leaving her dark roots intact.
The star promoted her HBO original film Grey Gardens in a shimmering headpiece Little Edie Beale herself would've loved.
Drew chose yet another '20s-inspired hair accessory for the Grey Gardens premiere, this one trimmed with a pretty veil. An era-appropriate Marcel Wave and red lip completed the look.
In what was perhaps Drew's most daring look to date, the actress went for a sky-high bouffant and frosty blue eyeshadow (!) at the 2009 Golden Globes.
2009 also saw the release of Drew's directorial debut, Whip It—and to promote the film, the actress appeared at an L.A. screening in minimalist bronze makeup and appropriately whipped-back hair. We think those beachy, wavy roots suit her beautifully.
Later on, at the Toronto Film Festival's Whip It premiere, Drew adopted a rock 'n' roll look that was completely in line with the film's quirky characters. She combined her mint manicure with heavily-lined eyes and a blunt-cut blond bob with daring, jet-black tips.
Peachy, pretty perfection at the 2009 Emmy Awards.
For the premiere of her star-studded chick flick He's Just Not That Into You, Drew opted for a Mad Men-era look with a flippy ponytail, dramatic cat-eyed liner and cotton-candy-pink lips.
Olé! We love this flamenco-inspired look Drew tried out for a 2009 appearance on the Late Show With David Letterman, from the full-sleeved Giambattista Valli dress to the slicked-back, braided bun and bold red lips.
Letting her avant-garde Atelier Versace do all the talking at the 2010 Golden Globes. Save for that tawny lip color, her face is essentially bare.

At the 2010 Screen Actors Guild Awards, mixing dark roots and a just-undone-enough beehive with a nude lip.


For the world premiere of 2010's Going the Distance, Drew wove tiny braids into her hair and chose a blackberry lip color, smartly leaving her eyes makeup-free so as not to compete.
Drew dove headfirst into 2011's Tangerine Tango trend, pairing her citrusy Jil Sander maxidress with mango-flushed cheeks and lips at a CoverGirl event.
Drew turned up at last year's New York City Ballet's Spring Gala on the arm of her husband, Will Kopelman. She looked tan, glowing and beautifully blissed-out.
Drew's returned to ombré hair time and time again over the years, and it's certainly a look that works for her. Ditto on that violet liner, which really makes her hazel eyes pop.