Then: Winona Ryder
Winona Ryder definitely took the world by storm during the 90’s. This was the time she appeared in Girl, Interrupted, Mermaids, Reality Bites, and Edward Scissorhands. In 1993, she took home the Golden Globe for Best Supporting Actress for her performance in The Age of Innocence. She also had a tumultuous personal life. After all, the actress dated the likes of Matt Damon and Johnny Depp!
Then: Winona Ryder
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