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Gwyneth Paltrow: Winona Ryder's Frenemy?

Gwyneth Paltrow: Winona Ryder's Frenemy?

In her latest GOOP newsletter, Gwyneth Paltrow talks about why the media spins stories negatively and mentions a “frenemy,” most likely referring to her former best friend, actress Winona Ryder. (Their friendship reportedly ended when Gwyn reportedly stole the part of Shakespeare in Love from Winona but Winona was never considered for the role.)

Gwyn writes, “Back in the day, I had a ‘frenemy’ who, as it turned out, was pretty hell-bent on taking me down. This person really did what they could to hurt me. I was deeply upset, I was angry, I was all of those things you feel when you find out that someone you thought you liked was venomous and dangerous. I restrained myself from fighting back. I tried to take the high road. But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and…happiness. There went the high road. So, why does it feel so good to hear something bad about someone you don’t like? Or someone you DO like? Or someone you don’t KNOW? I once asked the editor of a tabloid newspaper why all of the stories about a famous British couple had a negative bent. He said that when the headline was positive, the paper didn’t sell. Why is that? What’s wrong with us? I asked the sages to shed a little light. Here’s to washing our mouths out with soap… Love, Gwyneth.” Check out the rest of the Q&A at

The “unfortunate and humiliating” incident Gwyn mentioned is likely referring to Winona‘s 2001 shoplifting incident, where she stole $5K worth of designer clothes and accessories at a Saks Fifth Avenue department store.

Pictured below: Gwyneth and Winona holding hands and locking arms (1998-1999).

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gwyneth paltrow winona ryder frenemy 01
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Photos: WENN, KMazur/Ron Galella/Jim Smeal/WireImage
Posted to: Gwyneth Paltrow, Winona Ryder

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  • peaches

    Is this really newsworthy?

  • aeon

    Winona is beautiful.

  • Toronto_Boy

    I love the 90s looks… Less is more was so true … they are androgynously hot

  • slambang

    Shut up, Gwenyth, just shut up! Jeez.

  • Tess

    Noni really rocks the short hair. Gwynnie not so much. She looks pretty butch here:

  • mslewis

    I have no idea why their friendship ended but Winona was never up for “Shakespeare In Love” and that’s a fact. It was always Gwyneth’s part.

    Winona is beautiful but, in most of her movies, she has always been upstaged by a co-star. (See “Girl Interrupted” where people only remember Angelina.) Winona has no “presence” on the screen or in real life. Perhaps that’s why she began to hate Gwyneth because Gwyneth is at least memorable on and off screen.

  • mwahlberg

    Poor Winona. She’s trying to get her career back on track and doesn’t need this kind of negative publicity.

  • k

    Totally not newsworthy, and while I’m not a Gwenyth fan, it’s nice that she’s at least honest about it. She may say a lot of obnoxious, bitchy things sometimes, but she’s honest. The fake sweet bullshit that most celebs spout about each other while spreading shit behind the scenes is far more obnoxious in my opinion.

  • pr guy

    Ryder and Julia Roberts were both considered for the lead in Shakespeare in Love. It’s rumored Gwyneth saw the script in Ryder’s apartment and campaigned for the role. Personally, I can’t envision Ryder in the role, but it’s a shame Gwyneth has to pimp this stuff in her newsletter instead of letting bygones be bygones.

  • LolaSvelt

    #6, no it wasn’t. Many actresses turned down the role of Viola INCLUDING Winona Ryder, along with Julia Roberts and Kate Winslet.

    Anyway, I think it’s most likely Ryder. They were friends for a long time. They suddenly stopped being friends. Paltrow refers to this person doing something bad.

  • Marie

    Agree, Gwyneth does say a lot of obnoxious, bitchy things. Hard to find it endearing though when she’s lecturing everyone to “nourish their inner aspect” and chiding them about their “evil tongues.” It’s rather hypocritical. She should try following her own advice.

  • kismet

    Some women looks great with short hair, Paltrow is not one of them.

  • mickey

    Oh, Gwenyth SHUT UP! If Winona was a dangerous and evil toward you it’s because she was responding in kind.

  • shoegal421

    love noni…and miss the 90s. paltrow, not so much.

  • Jules

    Gwyneth looks like Winona’s mum in those pics.

  • melinda

    She’s ugly, dirty and nasty!!!

  • jenni

    Shut it Gwyneth, Winona Ryder is a goddess!

  • stacipoo

    Jared you should given Lainey credit as you basically took this from her website.

  • green is good

    ..and this “frenemy” tidbit just happens to come out around the time Winona starts promotions for Star Trek? Coincidence, I think not.

  • tawi-tawi

    #6 Gwyneth ia memorable??? hahaha, are you serious? i don’t remember her except for that movie, where she was fat…and probably only because she looked nothing like herself, while Whynona is great, and though she is been out of spotlight for really long time, people, i bet, still love and remember her…

  • scarlett

    She almost has a good message, but as usual, she delivers it the wrong way. If she were really above this bullshit, she wouldn’t be doing blind items like a celebrity gossip site.

  • t

    I have to give this woman credit. For someone who is not really a leading lady anymore and apparently not on the first-look list for scripts, she does a good job of keeping herself in the news through her goopy newsletter.

  • GOOP


  • anon

    didn’t Gywneth steal the script of Shakespeare in Love from Winona? I thought that was what ended their friendship.

  • GOOP


  • The Shiznack

    This bítch needs a cúnt punt!!!!!

  • Lovely

    Winona has two new films coming out: The Private Lives of Pippa Lee and Star Trek.

  • orion

    Isn’t Gwyneth sorta adding to the gossiping by telling us the frenemy story?

  • sandy

    I actually don’t mind Goop but this just feels like a passive-aggressive swipe at Winona. They had a very public break in their friendship. Most people will assume she’s referring to Winona and I’m sure Gwyn realizes that.

  • JenX

    I think Winona has aged much better than Gwyneth. Sadly, her career will probably never rebound from the shoplifting scandal. She also hasn’t transitioned to adult roles too well. Maybe Star Trek will change that? We’ll see…

  • Ingrid

    #24, if she stole it from her, it’s most likely that Winona would’ve never talked to her again. These pictures are from at the time of/after the release of Shakespeare in Love/

  • ALEX

    B i t c h!!

    Winona is so much better than you idiot!

  • Roxanne

    I find Gwynette comes across as a self-righteous b i t c h. She has great legs, that’s about it. Her face is jacked up.

  • uglysexy

    god winona is gorgeous but a piece of work if what they said in that cosmo article from ’03 is true…..but I’d much rather hang with her than
    with the 300 pound male bagpipe player who was pretending to be her last year on the imdb message boards….he had many people fooled

  • Naima

    Wow this woman is out of her mind, somebody needs to feed her a huge piece of humble pie. Winona is a far better actress than this idiot and funny that she forgets to mention that the real reason their friendship ended was because Gwyneth STOLE the Shakespear in Love script from Winona’s house and went behind her back and auditioned and from what has been said did a couple of “favors” for Harvey Weinstein which helped secure her role in the film.

    This witch gets more obnoxious and ugly by the day, Winona has had a hard time but she’s a far better actress and human being than this twat.

  • meine meinung

    two ex-gf from brad pitt

  • Marc

    I can see why Brad Pitt never married this bitch. And why he’s refusing to marry the pretentious, self-aggrandizing douche of a woman he’s currently with. Why do both of these women think they’re better than everyone else? Having now read several Goop newsletters, this woman has completely lost touch with reality.

  • EDS

    Gwynnie needs to take skiing lessons in Canada- without a helmet of course!

  • Jake

    Personally, I feel sad when something “unfortunate” happens to someone I dislike, if they have criticised me or not, not joyous relief.

  • n.o.l.a

    her newsletter make me hate her where as i was ambivalent before. she ruins iron man for me.

  • dana

    Team Winona!

  • Jake

    So should you just ignore people who harm or threaten others in their actions and not speak out about it?
    I think we should speak out about people who hurt others.

  • LolaSvelt

    @EDS: How could you say such a horrible thing? Not only did you offend Natasha Richardson, you also offended Gwyneth Paltrow. Hate her as much as you want, but she has a family and she’s a HUMAN BEING. You disrespectful cúnt.

    @meine meinung: Ryder never dated Brad Pitt.

  • jaye

    Gwyneth is memorable? The only thing memorable about her is that she won an Oscar and let it go to her head. I still remember that hideous pink dress she wore when she accepted the Oscar. She’s an elitist and self-serving.

  • Iris

    Gwyneth currently must be at pretty low stage that she feels the need to blame on someone for something happened years ago.

  • Regina

    I’m surprised no one has mentioned Madonna. They were rumoured to have had a fight and when Paltrow says that this person was humiliated, myabe she’s referring to Madonna’s failed adoption?


    No Harvey Weinstein hand picked her she was his muse back in ’98
    So no one else could take this part…So where did this come from eh?

    She did all her English movies Emma and all the rest with Harvey …
    why would a loser like Whinona take the role.. She did not let it
    go to her head…
    Stop second guessing .. O.K it could be Guy O Leary that she dated
    way back before he was famous.. or some other person in her life.



    No Harvey Weinstein hand picked her she was his muse back in ’98
    So no one else could take this part…So where did this come from eh?

    She did all her English movies Emma and all the rest with Harvey …
    why would a loser like Whinona take the role.. She did not let it
    go to her head…
    Stop second guessing .. O.K it could be Guy O Leary that she dated
    way back before he was famous.. or some other person in her life.


  • HA!

    Naima, I’m sorry to disagree with you but Gwyneth and Winona are BOTH pretty average actresses. Winona is definitely a prisoner of her own idiosyncracies; she never was able to melt into a role.

    It’s too bad if she IS talking about Winona because they seem happy as clams in the pictures together from when they were friends. Ending a friendship for these kinds of reasons must have been a really hard situation for both of them. Toxic even. I don’t remember the last time I saw pictures of GP looking as genuinely happy as she did in these pictures. Sad.

  • cathy

    congrats Jared. You made it – a mention in People is BIG TIME!!