She hasn't had a bad career

https://www.quora.com/What-happened-to-the-career-of-Winona-Ryder/answer/Matt-Cormier-2

A few things happened to Winona Ryder’s career the ultimately lead to her losing her stature as a Hollywood leading lady:

She Aged: By 1999 Winona Ryder was nearly 30 years old and was nearing the age that many actresses find their careers at a crossroads. No longer are they young enough to play “ingenue” roles and yet not yet old enough for “matronly” roles, and find that there is a lack of roles for them to play. She reached the height of her fame in 1988 when she was teenager (approximately 17–18) and by 1999 she was nearing the point of her career that she was fading out of popularity.

She Had Too Many Flops: Although she was once a critical darling and had starred in some movies that were box office smashes, by 2004 she had starred in just as many dismal failures and was beginning to develop a reputation as not being able to carry a film. Among the notable box office or critical flops she had were “The Crucible”, “Girl Interrupted” (against a budget of only 40 million it made a mere 48 million and change, a modest success but not a smash); “Boys”, “Autumn In New York”, “Lost Souls” and “Mr. Deeds.”

She Shoplifted: Winona had always had a fairly clean reputation, and wasn’t known for being a wild child or acting inappropriately, so it came as a bit of a shock when an otherwise “good girl” was suddenly in the news for something criminal. In 2001, Winona Ryder was charged with shoplifting in Beverly Hills after she was caught stealing 5,000 dollars worth of clothes from Saks Fifth Avenue. She was also accused during trial of using various drugs without a prescription and speculation in the press turned to Winona having a serious drug problem (speculation that was never confirmed and was seemingly nothing more than press creating rumors).

Damn crime we didn't get a 90s romcom with her.