Like...gag me with a spoon. That was our first reaction to the fact that our fave Doc Martens-wearing, angst-ridden '90s babe Winona Ryder is set to be in a Hallmark Hall of Fame movie. A piece of info she conveniently left out during a recent interview with Black Book magazine where she reminisced about her true icon years and babysitting Tom Waits, all while snarling into the camera like the Winona we know and love. Our first feeling was a punch-in-the-grunge-era-loving-stomach, but at the same time, this Hallmark move is a classic move. Here we revisit the epic highs and tragic lows of our fave blunt-bobbed Gen X pixie.
High: Heathers, 1988
Why: From the shoulder pads, the relentlessly catchy lingo, a homicidal Christian Slater, lunchtime polls, and Slushies, this was the original, no-holds-barred Mean Girls. With Drano. And croquet.
Quote: "Let's pretend I blew up the school...all the schools. Now that you're dead, what are you gonna do with your life?"
Low: Mr. Deeds, 2002
Why: As Adam Sandler's love interest, Ryder kind of made us cringe with her...well, her choice to be in a not-that-funny Adam Sandler movie.
Quote: "I know that I messed up real bad, and I'd be willing to spend the rest of my life begging you to give me another chance, because I am so deeply in love with you."
High: Dating Johnny Depp, 1990
Why: Well....because when you date Jack Sparrow, Edward Scissorhands, and Willy Wonka, we just have to tip our fedoras to you.
Cool Factor: Depp even had a "Winona Forever" tattoo, which he eventually amended to "Wino Forever" post breakup.
Low: Dating every musician imaginable (Dave Grohl, Beck, Evan Dando, Ryan Adams, Blake Sennet, Bono, Adam Duritz, Jakob Dylan, Chris Isaak, Stephen Jenkins, Conor Oberst).
Why: That doesn't make you a Band-Aid...we're not sure what it makes you.
Lame Factor: "You're no one in music until you have feuded with me or until you sleep with Winona," Courtney Love once said.
High: Reality Bites, 1994
Why: Ray-bans, grandma dresses, The Gap, MTV, and more awkward cool-talk from a grungey Ethan Hawke than you could ever remember on your own. Plus...Ben Stiller as a super random sort-of boyfriend.
Quote: "There's no point to any of this. It's all just a...a random lottery of meaningless tragedy and a series of near escapes. So I take pleasure in the details. You know...a quarter pounder with cheese, those are good, the sky about ten minutes before it starts to rain, the moment where your laughter become a cackle...and I, I sit back and I smoke my Camel Straights and I ride my own melt."
Low: Autumn in New York, 2000
Why: A ridiculous, sappy sweet May-December romance story between Winona and Richard Gere. More Girl, Interrupted than Pretty Woman, in terms of sanity.
Quote: "If you wanted to seduce me you could have just asked."
High: Beetlejuice, 1988
Why: She was the most fashionable little goth-turned-eventual-ghost we could have asked for, with a penchant for exorcisms.
Quote: "Well, I've read through that handbook for the recently deceased. It says: 'live people ignore the strange and unusual.' I, myself, am strange and unusual."
Low: S1mone, 2002
Why: Because no one even remembers it, and even with Al Pacino and Evan Rachel Wood, nothing could save such a bad, bad script.
Quote: "I am the death of real."
High/Low: Shoplifting scandal, 2001
Why: A low because, well, she stole a lot from Saks Fifth Avenue in Beverly Hills. A high because it seems like just the sort of anti-establishment "eff the man" move most of her teen characters would have pulled. Veronica, Lalaina Pierce...and especially Susanna Kaysen.
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