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BRIGHT-EYED AMBITION
The iconic brunette sported lighter locks as a teen in the mid-'80s.
GOLDEN GIRL
Ryder posed with her Square Dance costar Rob Lowe at the 1988 Golden Globes.
GOOD TO BE BAD
In 1989, the then-17-year-old actress smiled on the Academy Awards red carpet alongside her Heathers cast mate Christian Slater.
WHITE HOT
The actress chose an all-white getup for the 1989 premiere of Great Balls of Fire, at which she met her soon-to-be-boyfriend Johnny Depp.
STAR POWER
Ryder scored her first-ever Golden Globe nomination for 1990's Mermaids, in which she starred alongside Cher and Christina Ricci.
MAKING THE CUT
The Edward Scissorhands star laughed it up with director Tim Burton, costar/boyfriend Johnny Depp and composer Danny Elfman at the film's 1990 premiere.
GOT THE SPIRIT
A feisty Ryder, here in 1990, got goofy after landing in Los Angeles.
AWARD-WORTHY
Then-couple Depp and Ryder kept it dark and mysterious at the 1991 Golden Globes.
BITE OUT OF LIFE
Ryder sported a romantic look at the 1992 premiere of Dracula, which also starred Sadie Frost and Gary Oldman.
CLASSICALLY CUTE
The actress shined on the 1996 Oscars red carpet.
BEST BUDS
Ryder and fellow '90s queen Claire Danes became friends after working together on 1994's Little Women. They proved their bestie status with matching red lips at the 1996 Fire & Ice Ball in Burbank, California.
HUG IT OUT
Courtney Love embraced the actress at a cocktail party in 2000.
DATE NIGHT
Ryder attended the 2000 Globes with then-boyfriend Matt Damon, whom she met through friend Gwyneth Paltrow.
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