Winona's post 90's career is embarrassing but her 90's work easily surpasses anything Gwyneth has done. And it's not like Gwyneth did much in the 2000s either, her most noteworthy role was as Iron Man's girlfriend.
Watching Ryder in Black Swan was kind of heartbreaking through. The irony of her playing a troubled hasbeen who's career was ruined from a mistake and then gets replaced by a younger version of herself. Perfect casting, but damn....
