A Pictorial Retrospective of the Coolest Goddamn Chick of the 90s

true detective /hannibal / dc movies / snl / mindhole blowers / netflix / celebrity facts / marvel

A Pictorial Retrospective of the Coolest Goddamn Chick of the 90s

By Dustin Rowles | Seriously Random Lists | July 24, 2012 | Comments ()






















David Beckham Is Here To Crumple Your Cynicism Into A Ball And Punt It Across The Goal Line | 9 Huge Plot Holes in The Dark Knight Rises That Totally Don't Work

Are you following Pajiba on Facebook or Twitter? Every time you do, Bill Murray crashes a wedding.

Comments Are Welcome, Bigots and Trolls Are Not

  • e jerry powell

    If we're being real, that header picture makes her look more like Jennifer Beals.

  • Strand

    She shoplifted my attention

  • maxpurr

    this was my fav of her and gary. so adorable. the both of them. swoon
    (+ beetlejuice forever!)

  • ,

    Plus, she can get you anything you need at Saks at a discount.

    How cool is she?

  • jamie pants

    I saw the header pic, which looked nothing like her to me at first, and thought, "Uh, hell no, I don't know who this bitch is, but Winona Ryder...oh."

  • BarbadoSlim

    Is hot the new synonym for textbook case study in merchandise loss prevention?

  • TheOriginalMRod

    We will always have Heathers. But now she is Spock's momma. And we still have all the chicks who look just like her... Kiera Knightly... sometimes Natalie Portman, and a little Lizzy Caplan. I know there are more, I just can't think of them right now.

  • chriso

    I'm sorry, but once she stopped playing angst-ridden teens it was just like a speeding toboggan ride into crapville.

  • Fher

    I was born in 1985, im a gay guy , but she´s always gonna be my first crush. And i always get excited when i see her on any of today´s movies, like black swan or star treck.

  • And now my hatred for Adam Sandler has increased 10 fold. After Mr.Deeds it was all downhill.

  • stardust

    Man, I love her. She will always be one of my favorites.

    Side note: I can always peg a picture as belonging to the 90s by the makeup. A perfectly lined reddish-coral lip and brown or peach eye makeup is always a dead give-away.

  • Jo 'Mama' Besser

    Or that brown MAC lipstain that made your lips peel, or Revlon Blackberry

  • Cuca

    If only we could have Winona back, instead of stupid, bony, word-bitting Keira!

  • e jerry powell

    Does it not bother you that everybody in this school thinks that you're a piranha?

  • Jezzer

    They all want me for a friend or a fuck.

  • e jerry powell

    I'm worshiped at Westerburg, and I'm only a junior.

  • bev rage

    You were nothing before you met me. You were a Bluebird. You were a Brownie. You were a Girl Scout cookie.

  • e jerry powell

    Ooh, whiplash to a later scene...

  • Malware

    That was some DAMN fine nostalgia right there, now I need to go download some of these movies and watch them all over again.

  • Slash

    I do kinda miss the grunge aesthetic (if it can be called an "aesthetic"). It was nice, wearing comfortable clothes and still being somewhat "in style." Maybe I should try to bring it back. I miss Winona, too, BTW.

  • Rebecca Hachmyer

    No Jo March? Blast this wretched retrospective!

  • PerpetualIntern


  • yep.

  • bdog

    Man, I wish she worked more, she's the cat's ass.

  • Nieve 'The Threadkiller Queen'

    I miss Winona.

  • John W

    I'm hoping that she has a Robert Downey type resurrection to her film career.

  • growler

    It might happen. She was great in Black Swan, and even though she had little screen time, she really stood out and made an impact.

  • John W

    She's still beautiful.

  • Stephen Nein

    And now, Winona is playing Zach Quinto's dead-eyed mother.

    This sucks more than no flying cars.

  • Arran

    Ohhhhhh Winona. If only this article were true.


  • A. Smith

    Wow, I remember when I was a kid thinking pretty much the same thing. Now what is she... she's Spock's mom. I don't know how you can top that.

  • danobc

    omg, i am having such a nostalgia fit of the 90's when smashing pumpkins were cool, when backstreet boys were stil around, when photos were oversaturated (like the one where she is eating ice), when the world wasn't all hipster zombie and more like ZOOOOMBIE ZOOOOMBIE, IN UUUURR HEAAAAAAAD IN YOOOOOOUR HEAAAAAAAD

  • Oh, the Backstreet Boys are *still* around.

    I mean... uh... I don't know what ever happened to those guys....

  • danobc

    i'll get snark for this, but i couldnt even tell if they are still around because i know them from MTV but that channel doesn't exist anymore the way it did in the 90's. ya know, with music and all, even if it was Backstreet Boys and N'Sync (OH GOD THE MALE HAIRCUTS, yeah i know what i am not missing) and the ocassional Daria.

  • No Pithy Name

    Damn, I hate Reality Bites. Being a native Houstonian I can't make myself get past the fact that nobody lives anywhere like that around here, certainly not in the 90's. It seemed like the writers decided to make a pretend hipster version of downtown so the characters could have somewhere interesting to live.
    But yeah, she's pretty cool. Easy on the eyes, too.

  • Arran

    I don't know why they chose Houston. Wouldn't Austin have made more sense?

  • Sturm & Drag

    Not really sure what that pic of Hobo Keanu on a bike is doing here.

  • anatomycoloringbook

    That's from Welcome Back, Roxy Carmichael.

  • danobc

    thats the best one. it reminds me of myself in the 90's. when looking like a grung aftermath hobo was cool.

  • Jill

    Her hair style from Reality Bites could beat the shit out of the Rachel (sp? That's how much I don't care.) any day.
    That is THE best female hair of the 90s. For sho.

  • anatomycoloringbook

    I did too. In fact I did cut my hair like that. I did not look like Winona. Not at all.

  • ljridley

    Right!? I wanted that hair so bad and I so don't have that hair.

  • lowercase_ryan

    I know Winona had the more impressive decade career wise, but I will take Parker Posey hands down as the coolest chick of the 90's. To this day I looooooove that woman.

  • I will love her forever.

  • Samantha Klein

    Clicked on Twitter link, said aloud, "Better be Winona Ryder." Win!

  • Maguita NYC

    Wyno Forever!
    How passionate the 90's were with Johnny and Winona. Would she still be interested in him today?

  • kimk

    For reasons that have nothing (i.e., everything) to do with nostalgia for my misspent youth in the '90s, a little part of me pines for these two to get back together.

  • Maguita NYC

    hhhhaaaaaaah. But Johnny has lost his looks, drinks too much, has somewhat of a gut, and is (allegedly) sleeping around with women half his age. He is going through the most embarrassingly-tacky stage in a man's life: Mid-life crisis.

    Menopausal Wynona would never dream of being this tacky. Not even high on Demeral while shoplifting at Macy's.

  • I'm ready for her to have a Robert Downey Jr-esque career resurgence.

    Winona Forever.

  • e jerry powell

    Complete with multiple arrests and stints in rehab?

  • sean

    I don't think women get those in Hollywood. I do miss her however. I still have a huge crush on her. Even though we both are middle aged now.

  • I will take Parker Posey hands down as the coolest chick of the 90's...StartProjectMillionaire.blogspot.com

  • the_wakeful

    Having just rewatched party girl (live! with the director!), I concur.

  • Fabius_Maximus

    Don't feed the spammers.

  • lowercase_ryan

    what kind of fuckery is this???

  • danobc

    for some reason i was thinking about her today and asked myself whatever happened to her? is she still as mesmerizing? is she still charming in a female johnny depp kind of way? and then i see this. holy cow...mind blown

    AH I GOT IT!!! i looked at my bar on the desktop, justified is playing! bitchy winona was what made me think of cooooooool winona.

  • Genevieve Burgess

    ... Keira Knightley?

    I kid. But seriously, a couple of those pictures are uncanny.

  • F'mal DeHyde

    Minus the monstrous jaw and constipated look.

  • Lee


  • Miss Laaw-yuhr

    Yup, purple dress was all Keira Knightly, but the brown jacket was all Edward Furlong.

  • Sara_Tonin00

    I thought the same thing. But with boobs.

  • emmelemm


  • danobc

    she looks like a next door girl keira knightley, she is more "effable" than knightley. (i love that word btw)

  • *SWOON*

blog comments powered by Disqus