Winona Ryder

There's no question that Winona was the ultimate It girl of the late '80s and '90s, but, following her 2001 shoplifting arrest, Winona was never able to bring her career back to its pervious A-list level. Although Winona has had small roles in critically acclaimed films like 2010's Black Swan and 2012's The Iceman, she has yet to take on a major role. Maybe that's by choice, but personally we would love an opportunity to see Winona break back into the limelight with a good role. After all, we still remember thinking Johnny Depp tattooing "Winona Forever" on his arm was the most romantic thing ever.

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