I recently rewatched Heathers for the 100th odd time (though it's been years since I last saw it). This film is every bit as subversive, clever and witty as it was when it was first released, and this is due to a number of things: Daniel Waters' whip-smart screenplay, young Christian Slater at the height of his outcast mystique, but mostly because of Winona Ryder's scarily humanistic portrayal of a complete sociopath.
Fast forward through Generation X, where she was one of the big stars, and look at her now. She's consigned to irrelevant roles like her 2 minutes in Star Trek or her Norma Desmond grotesque in Black Swan. But in many ways, the character she plays in Black Swan is the perfect reflection of herself. She dazzled the world with her artistic talents in her youth, then she's shoved aside in favor of the younger star, but she definitely does not go quietly.
It's astonishing to think that an entire archetype would not exist without Winona Ryder: the moody outsider who flies dangerously close to the dark side but never loses her firm belief that the world has no purpose except to provide a vehicle for her sarcasm and narcissism (there have been many male characters of this nature, but Ryder's take is uniquely female, and infinitely more strange than the Holden Caulfield type). Teen girls would never be the same. There would be no Mean Girls or Buffy without the road paved by many classic Ryder characters.
But all this got me thinking: what the hell happened? Where did it all go wrong? I don't have a definitive answer, but one thing is obvious; Winona Ryder is making the same journey made by many a politician.
So Winona starts out angry and ready to take a stand in Heathers. But she quickly learns, thanks to Christian Slater, that direct action is initially life-affirming but can end up blowing up in your face (quite literally in this case). You live life on the edge and you want as many people to know about you as possible (Wino Forever!).
Then, In Reality Bites, we're basically watching phase II of Veronica's growth as a political activist. We see her compromise her ideals in the hopes that compromise can lead to actual movement. But just as the day-to-day business of politics seems to corrupt its essential participants, this means that Lelaina sells out (to Ben Stiller!), and ends up destroying her budding career.
So as we all know, politicians have three options when they get voted out of office: you can attempt to redefine your identity, you can turn to a life of crime in the form of lobbying, or you can go straight to jail. Winona Ryder managed to do all three. Redefining herself took the form of period dramas such as Age of Innocence, Dracula and The Crucible, all of which are terrible. They are terrible mainly because Winona has to play fragile characters, flowers hiding from the sun, so they waste her particular appeal (and also there are multiple dodgy accents). (Little Women is great though). Repeated failure can make politicians crazy (see John McCain), and so went Winona - she ended up in the loony bin (Girl, Interrupted). But she wasn't the looniest in the loony bin, so people only remember Angelina Jolie from that movie.
So, just like McCain, this apparently inspired Winona to ramp up the crazy. Which brings us to the Free Winona! phase of Winona's journey (aka life of crime and straight to jail, all in one). A career crash of such epic silliness is hard to imagine, and hasn't been matched until Britney Spear's similarly unforeseeable breakdown. Supporting evidence for craziness: co-starring in an Adam Sandler movie.
So the inevitable followup to a highly publicized flameout is steady obsolescence. And so it seems that after this rollercoaster journey, Ryder is doing the actorly equivalent of the quiet retirement to the ranch - character roles. I for one can't wait to see her next act. Which, if I had to predict using this labored metaphor, probably means she'll become a pundit on CNN or Fox News.