Gwyneth Paltrow & Winona Ryder’s falling out was even worse than people imagined

More excerpts and scandals from Amy Odell’s latest book, Gwyneth: A Biography. It definitely feels like the most gossip-worthy sections are from the 1990s, Gwyneth’s heyday and the decade which saw her rise to power. After Gwyneth and Brad Pitt broke off their engagement, Gwyneth quickly began dating Ben Affleck. It was such a power move – Ben’s star was also on the rise, and there was a built-in compatibility within the friend group. Ben’s bestie was (and is) Matt Damon, who dated Minnie Driver and then Winona Ryder during that time. Winona and Gwyneth were friends as well, until they weren’t. Gwyneth and Winona had some kind of falling out at some point in the late 1990s, and the fallout rumors were mostly about the Shakespeare in Love script (which Odell fact-checked and wrote that the role was always Gwyneth’s). But Odell did get to the bottom of Gwyn and Winona’s fallout and it’s awful. Gwyneth is awful.

In Gwyneth: The Biography – published July 29 – journalist Amy Odell reveals Gwyneth Paltrow was once close friends with Winona Ryder but grew to despise her after suspecting her of fabricating stories for attention. At the time, Paltrow was dating Ben Affleck and Ryder was dating his best friend, Matt Damon – making the two couples a Hollywood power foursome until the actress’s friendship with the pair soured.

In the late 90s, Paltrow’s star was on the rise although she had not yet starred in the role that would earn her the Oscar for Best Actress – Shakespeare in Love. Yet Odell writes that she had a habit of burning through friends on her way to the top, and that included Ryder. After breaking up with Brad Pitt in 1997, Paltrow moved into Ryder’s house, apparently for consolation from her friend, but their friendship would soon crumble.

According to the book, following an argument between Ryder and then-boyfriend Damon, Ryder left their New York apartment to say she had been robbed. Then Ryder left the home a second time, came back and claimed she had been robbed again. While Damon was sympathetic, Paltrow was convinced it was a ploy for attention and from there, the friendship deteriorated.

‘Damon consoled her but Gwyneth and Affleck believed Ryder fabricated the robberies as a ploy for attention (there’s no proof of this),’ the book states. ‘Gwyneth was annoyed that Damon couldn’t see it. Though Damon was kind to her friends, Gwyneth didn’t seem to like him after that. Her friendship with Ryder would only deteriorate further, and Gwyneth gave her the nickname “Vagina Ryder”.’

Ryder and Damon began dating after the actor had split with Driver, whom he met on the set of the movie Good Will Hunting. Driver would later claim that she only realized Damon had dumped her when he went on the Oprah Winfrey Show and said he was single. But Paltrow told friends that this was ‘untrue’.

‘Gwyneth understandably wanted to take her boyfriend’s friend’s side but she also seemed to sour on Driver,’ Odell writes. She considered Driver an ‘air-kiss friend’ and disliked her alleged ‘fake’ aristocratic persona. Once while doing a photo shoot at a rented house in Los Angeles, Paltrow swallowed her distaste for Driver and organized a last-minute birthday party for her.

‘When Driver wasn’t looking, Gwyneth rolled her eyes to friends and mimed vomiting by putting her finger in her mouth,’ the book states.

[From The Daily Mail]

Gwyneth is such a douche, my god. This is how she used her social currency and cultural power: to be a nasty Mean Girl to her girlfriends and their boyfriends. Now I want to know more about Winona’s robbery claims too – what the hell happened when Gwyneth moved into Winona’s house? And Gwyneth’s hatred for Minnie Driver is so f–king random, omg. Gwyneth hated Minnie because Minnie… had an authentic British accent. Minnie didn’t pretend to be an aristocrat back then either! She wasn’t the one starring in Jane Austen adaptations and costume dramas. That was Gwyneth!


.

Photos courtesy of Cover Images, Ron Wolfson/Avalon and Look Press Agency/Look Press/Avalon.

You can follow any responses to this entry through the RSS 2.0 feed.

56 Responses to “Gwyneth Paltrow & Winona Ryder’s falling out was even worse than people imagined”

  1. Thinking says:

    She didn’t like Damon because he actually believed his girlfriend? That’s a little weird..

  2. ThatGirlThere says:

    Gwyneth was a nasty little gremlin. I’m sure her distain for Winona and Mini was jealousy. Talking shit and creating drama is nasty work by Gweni.

    • atorontogal says:

      Absolutely agree. She’s always been an insufferable mean girl imo. And who told her she could act? Her mother was an OK actress and I honestly don’t know much about her father, but simply because she comes from acting stock, does not mean she has the gift.

    • Mightymolly says:

      ITA! I can’t stand her, never have, but calling out Driver for being a fake aristocrat? OMG. The lack of self awareness in this one

    • StillDouchesOfCambridge says:

      Minie was everywhere wasn’t she? And at the time, I remember she was always the one dating the most popular dudes. Tom cruise maybe?

    • Bananie says:

      Came here to remind everyone that GOOP MADE THIS MOVIE and it is laughably BAD.
      https://www.gofugyourself.com/fug-the-fromage-country-strong-06-2011
      God bless the Fug Girls.

      • Jessi says:

        Country Strong is such a fun movie to clown on – it’s so melodramatic, no cliche is left unturned, and the only character who doesn’t sing is the only legit country star in the cast. It’s completely bonkers and I recommend it!

      • Deering24 says:

        Heh. One suspects Gwyneth was hoping this would reignite her career by appealing to the “heartland” crowd. They were the most brutal about it. 😂😂😂And I’d give a million to hear Beyonce tackle this character’s signature song, for it is right good.

  3. SDG says:

    The ultimate Nepo Baby, Goop, is such a bite in the arse. She rubbed me the wrong way from the start and she has only gotten more irritating as the years have gone along. I guess first impressions die hard.

  4. MaisiesMom says:

    So Winona let Gwyneth move in with her post break-up to help her through it, and Goop reciprocated by not believing her friend when she said she’d been robbed? With friends like that who need enemies, as they say.

    I remember the first time I saw Paltow being interviewed, how struck I was by the difference between her film persona (I do think she can act and can really light up the screen) and her actual self. She was smug, dull, and humorless. And it was a sort of comedy talk show format. She couldn’t play along at all. She’s just no fun and apparently not a very nice person either.

  5. SamuelWhiskers says:

    Okay but by all accounts Winona Ryder was absolutely psychotic back in those days. There are so so many stories of her being abusive and evil to people.

    Goop I think is insufferable but she’s always had a rep for being basically polite, albeit condescending.

    • Thinking says:

      I do think Winona has or had a rep for telling tall tales, but I also think it makes sense Damon believed her. I think it would be worse if he didn’t…

      Gwyneth wouldn’t have the same blind spot as Damon so her disliking him for believing the woman he’s in a relationship with is still odd to me.

    • Manny K. says:

      I honestly don’t remember Winona ever having been described as abusive or evil. In fact aside from the shoplifting arrest, I don’t recall ever hearing a single bad word about her,.

    • Not A Subject says:

      I would not be surprised at Wynona lying. Remember when she was caught stealing all those coats. I think a lot of creatives have bipolar or hystrionic or other conditions. There’s really not enough info on this to make a judgement on either of these two.

  6. Sue says:

    I read everything about Gwyneth in her pretentious “bad Jackie Kennedy impression” accent.

  7. A lot of time has passed. It would be cool if they could be friends again. Oh well. Winonaforever💘

    • Josephine says:

      A lot of time has passed, and I have no idea how any of this information could possibly be verified. People remember things very differently, even when not loaded with fault and blame. I frankly believe nothing except that none of these people sounds nice, reasonable, or trustworthy, and every one of them has a reason to skew the story their way.

      • Yvette says:

        @Josephine … I remember the bit about Gwyneth running away to NYC to stay with Wynona after breaking up with Brad because of a random date stamped photo of Paltrow and Rider, all smiles and giggles with drinks, with a blurb in a magazine about ‘the friends’ partying together in NYC.

        And then one of the gossip columnists (it might have been Ted Casablanca with E!) went into detail about it with a timeline in a column. The gist was that Gwyneth initiated the break up and broken engagement by confessing about an ‘affair’ to Brad when confronted.

        It then occurred to me that the blurb I’d read with the, smiles and giggles, photo was from just after the break up. What I also distinctly remember thinking is that Gwyneth didn’t look ‘broken up’ about the break up at all.

  8. Mightymolly says:

    Remember when Gwenyth’s severed head was in that box?

  9. Betsy says:

    The Apple doesn’t fall far from the tree, apparently.

    • Nivz says:

      Can’t believe this comment doesn’t have a million likes.

      • Betsy says:

        Snort.

        Apple was expelled, she was such a mean girl.

      • Deering24 says:

        Whoa, what?! Really?! Tea, please…and thanks! 🙃

      • Betsy says:

        She was expelled from Harvard-Westlake for bullying an African-American girl into a suicide attempt, including the N word. Also she charmingly mocked other students for not having as famous parents as hers.

      • Marion says:

        @Deering24 There’s a rumor (or not) that she was expelled from school because of bullying. While I don’t know whether it’s true, I can believe that considering her attitude at the Bal des Débutantes

      • mightymolly says:

        WTaF?!? I don’t know anything about Apple besides her dumb name and that she inherited her mother’s conventionally attractive slender blonde looks, but what does Apple lack in her life? Like seriously what one thing does Apple crave that she doesn’t have? Goop bullying other Hollywood A-Listers is obnoxious but being a racist A-Hole? That’s beyond redemption.

      • Betsy says:

        I think Apple looks more like Chris than Gwynnie, but that’s a good thing because she’s so homely.

        My good friend is her Hamptons gardener, that is, keeps all the veg going all summer for when G. shows up, and she says she’s always stoned and out of it.

      • Deering24 says:

        Holy shit!!! 😳😳😳 The hits just keep on a-coming’ with this family. Proof, once _again_, that snobbery is straight-up stupidity. And having everything ain’t everything. Thanks, guys!!

  10. Stephanie says:

    I read somewhere that Paltrow only wanted to live with her bc she could find out about the parts she was going for and possibly take them from Ryder.

  11. Digital Unicorn says:

    Goop always had a rep for using people esp other famous people. Still does it.

    She’s not a bad actress however she did not deserve that Oscar which made her even more insufferable than she was.

    Also Winona at that time was struggling with her MH and fame. Plus didn’t she struggle with a pain med addiction at the time as well?

    I always thought Goop was butt hurt that Ben wasn’t the kind of partner that Matt was/is. I have always preferred Matt who seems like a good decent guy who seems to adore his wife.

  12. HillaryIsAlwaysRight says:

    Minnie Driver was tall, thin, and competition for acting jobs. Her body was work out goals in the 90’s (after gaining and dropping weight for Circle of Friends). So of course Goop would be jealous and resentful of her. Sounds like Goop was nice to her to her face while she had to be (friends in common), but made fun of her behind her back. Classic mean girl moves.

  13. Bookie says:

    I just received my copy in the mail yesterday and started reading it last night. You guys – it is such a great hate-read! I am purposely not reading this Gwenyth/Winona post because I don’t want to spoil it for myself when I get to that part. Gwenyth is awful!

  14. bisynaptic says:

    “According to the book, following an argument between Ryder and then-boyfriend Damon, Ryder left their New York apartment to say she had been robbed. Then Ryder left the home a second time, came back and claimed she had been robbed again.”
    — This is very strangely worded.

    • Thinking says:

      It is, right? I kept staring at the sentence — it didn’t make sense. And so much information seemed missing in between point A (she left their apartment) and point B (to say she was robbed).

  15. FYI says:

    “Ryder left their New York apartment to say she had been robbed. Then Ryder left the home a second time, came back and claimed she had been robbed again.”

    Trying to figure this out. The author (and her editor) should’ve clarified this. She left their apartment to say she’d been robbed? Left to say that to whom? The police? It makes no sense as written.

    • Manny K. says:

      Very confusing. Like left to make a police report and then there was even more stuff missing? Like the robbers came back? We’ll need another journalist to get to the bottom of this sentence.

  16. LolaB says:

    In general I tend to hate-read anything about Gwenyth, but I am 100% here for this hot 90’s gossip. The exerpts from this book are so amazing.

  17. KC says:

    This all so very …believable.

  18. Ollie says:

    I don’t really know what to think about Paltrow not believing Ryder’s statements that she had been robbed twice but clearly, Ryder had some issues; in 2001 she was sentenced to three years probation, 480 hours of community service, and a hefty fine for shoplifting.

  19. Anony vas Normandy says:

    Remember when we used to call her Fishsticks? Good times.

  20. M says:

    Paltrow has always been a douchbag. She will always think she’s above everyone and we’re all peasants.

  21. MY3CENTS says:

    That top photo of Gwyneth next to Winona just makes it so clear how very basic and ordinary Gwyneth was. Winona is the real star,always has been.

  22. Marcia says:

    Idk. I was in my 20s once, too. And my behavior was often cringey and high drama. It’s not the most mature decade of one’s life. 🙂

    • martha says:

      Yep! I suddenly flashed on how cold-hearted + ruthless I was when breaking up with boyfriends at that age.

      Hmmm – now that I think about it, the reverse was also true. Guys breaking up with ME were pretty cold, too!

      Absolute emotional immaturity all around.

      Thank god I’m a nobody

      • Marcia says:

        ITA. I didn’t behave all that well and wasn’t all that nice sometimes, and sometimes the guys did the same. And my friendships were sometimes messy, too.
        I’m glad all my past crap isn’t out there for public consumption! 🙂

      • TBag says:

        What I conclude from this is that people are all freaking the same.

        I don’t know if that’s a good or bad thing

  23. Mtl.ex.pat says:

    Always loved Winona – she did have some issues that led to the whole shoplifting incident. I was glad when she took time for herself then relaunched her career. I’m of the age when in my late teens early 20’s she was everywhere – and just so, so effortlessly cool.
    Minnie Driver never pretended to be aristocratic or whatever nonsense Goop is spewing. To the contrary I remember seeing her on talk shows and she had a great self-deprecating sense of humour. She seemed like a lovely, funny outgoing woman.
    And Gwyneth – I’ve said it before & I’ll say it again – without mummy and daddy she’d just be another average, plain blond girl without an Oscar (sorry not sorry – few celebrities set my teeth on edge like she does!)

  24. j.ferber says:

    Gwyn’s nose has been worked on since the header picture. Very obviously.

  25. Serena says:

    This isn’t surprising at all, Gwyneth has always given off the mean-girl vibe – a bully who looks down on everyone. And it seems her daughter is just like her – though I hope I’m wrong.

  26. East Villager says:

    I can’t speak to what she was like in the 90s but I have friends in common with Minnie from her recent years living in Malibu, and she is truly beloved in that community. Very down-to-earth, considerate neighbor, etc. A lot of rich people live in Malibu, but the long-time residents are genuine and very particular about who they welcome. You cannot live there and be an a-hole without word spreading.

  27. Hailey says:

    I’m still upset that Gwyneth won the Oscar for Best Actress over Cate Blanchett. Her acting is just to bland and fake to me.

  28. Bea says:

    It sucks that I can honestly see Winona lying about the robbery, and yes for attention. And I still have to say she’s more likable than Gwyneth Paltrow.

  29. LeaAnnshelookslikeaman says:

    Tragic mean girl pick me. Milla Jovovich is a wayyyyyyybetyer actress. Gwynnie wishes.

Commenting Guidelines

Read the article before commenting.

We aim to be a friendly, welcoming site where people can discuss entertainment stories and current events in a lighthearted, safe environment without fear of harassment, excessive negativity, or bullying. Different opinions, backgrounds, ages, and nationalities are welcome here - hatred and bigotry are not. If you make racist or bigoted remarks, comment under multiple names, or wish death on anyone you will be banned. There are no second chances if you violate one of these basic rules.

By commenting you agree to our comment policy and our privacy policy

Do not engage with trolls, contrarians or rude people. Comment "troll" and we will see it.

Please e-mail the moderators at cbcomments at gmail.com to delete a comment if it's offensive or spam. If your comment disappears, it may have been eaten by the spam filter. Please email us to get it retrieved.

You can sign up to get an image next to your name at Gravatar.com Thank you!

Leave a comment after you have read the article

Save my name and email in this browser for the next time I comment