I recently came across a photo of Gwyneth Paltrow and Winona Ryder while doom scrolling. They were in a restaurant, both in black, Paltrow in leather trousers, Ryder holding a beverage, both looking out of the frame, both with open mouth smiles, as the photographer’s bright flash captured the very elite and specific 90s vibe of it all.
I zoomed in, not sure why, maybe I thought I’d be able to see what they were talking about. But all I thought was, that’s right, they were the it best friends.
Hollywood and Friendship
Paltrow and Ryder were one of the defining Hollywood friendships of the 1990s. They hung out, partied, and even lived together. At the time, Ryder was the actress of her generation. She’d already starred in Beetlejuice, Heathers, Edward Scissorhands, The Age of Innocence, Reality Bites, Little Women and been nominated for an Oscar twice. Not only was she incredibly talented, but Ryder was already a cultural phenomenon known for being smart, beautiful, and effortlessly cool.
Paltrow on the other hand was seen as an actress that was “well positioned” aka nepo baby. She’d appeared in films like Se7en and Emma and was starting to be recognised for having a more polished, classical screen presence. She was nowhere near being the defining cultural figure she is today.
The two were so close that Paltrow moved in with Ryder in her New York City apartment after she broke up with Brad Pitt in 1997.
90s Cool Couples
My personal highlight of Paltrow and Pitt’s relationship were:
A) Their matching haircuts and outfits
B) The story we discovered much later of Pitt protecting Paltrow from Harvey Weinstein.
Paltrow told Howard Stern on his Sirius XM radio show in 2018 that on one occasion Weinstein, who’d hired Paltrow for Emma, suggested she give him a massage. When Paltrow told Pitt he confronted Weinstein at the opening of Hamlet on Broadway.
Paltrow details:
“He said, ‘If you ever make her feel uncomfortable again, I’ll kill you.’ Or something like that. It was so fantastic. He leveraged his fame and power to protect me at a time when I didn’t have fame or power yet.”
Despite his chivalry, and willingness to match her sartorially, Paltrow ended their engagement because she didn’t feel ready to tie the knot. So, what’s a girl to do after a breakup but move in with her bestie? At this point in time, pre Madonna, bestie in question was Ryder.
Shortly after, Paltrow started dating Ben Affleck (so random, don’t have time to get into that) who was Hollywood’s it boy after Good Will Hunting fame. Paltrow then introduced her bestie to Affleck’s bestie.
Matt Damon, also newly arrived Hollywood it boy after Good Will Hunting fame, started dating Ryder and the four of them became a defining 90s thing - always dishevelled in a glamorous way, they were positioned as this ultimate “cool” couple group. But all cool things must come to an end.
Beginning of the Breakdown
According to the unauthorised biography Gwyneth: The Biography by Amy Odell, published in 2025, Paltrow was allegedly getting frustrated that Ryder was either exaggerating or fabricating stories about being robbed whenever she and Damon would get into a fight. Whether it was an attention seeking move or a way to one up him in an argument, if true, both reasons sound completely deranged to me.
Paltrow and Ryder’s friendship got so bad at one point that Odell writes:
“Her (Paltrow) friendship with Ryder would only deteriorate further, and Gwyneth gave her the nickname ‘Vagina Ryder.”
Theft, Rumours, Oscars
I mean… while ‘Vagina Ryder’ is linguistically creative, if true, it’s quite mean spirited. For most this would be the final straw, however, it seems the actual straw that broke the back of the 90s BFFs duo was when Paltrow allegedly stole the script of Shakespeare in Love from Ryder’s coffee table, auditioned for the role, got it, and eventually won an Oscar for her performance.
Paltrow told friends that Ryder started the rumour and insisted she’d received the script through her agent. It doesn’t matter, this story, over any other, from their friendship is the one that has persisted over the years. I wouldn’t say it’s haunting Paltrow, as I really don’t think she cares in the end of the day, but she has addressed the rumour in veiled and direct ways over the years.
In April 2009, in the weekly Goop newsletter, Paltrow made mention of a person that most people suspect is Ryder. She wrote:
“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.”
Courtroom Muse
The incident Paltrow is likely referring to is Ryder’s arrest in 2001 on suspicion of shoplifting designer clothes and accessories from Saks Fifth Avenue. There were 19 items stolen, including a Marc Jacobs thermal, a white Yves Saint Laurent blouse, and a black Natori handbag. We all remember the CCTV footage that was shown on the news, which in hindsight, like many things from the later 1990s and early 2000s was absolutely manic to share, actually.
I, always a Ryder fan, believed her when she told the security guard who caught her:
“I’m sorry for what I did. My director directed me to shoplift for a role which I was preparing.”
The jury didn’t buy it or her list of other defences including researching for a role, her mental health, and medication, affecting her judgement. She was convicted of grand theft and shoplifting, acquitted on the charge of burglary and sentenced to three years of probation, 480 hours of community service and some fines.
It should be noted that in her courtroom appearances Ryder was dressed impeccably in Marc Jacobs – one would assume she didn’t steal those outfits. Her polished look in court lead her to star in Jacobs’ Spring 2003 advertising campaign.
Jacobs told Women’s Wear Daily at the time:
“I asked Winona to do the campaign because I thought she looked so beautiful in all these pictures that we’ve seen recently, regardless of whether they were from the trial.”
Whatever her reasons for stealing, the whole thing ended in an interesting arc – the thief became the muse. I’m sure Paltrow’s feelings of “deep relief and… happiness” weren’t related to the wholesome conclusion to Ryder’s brush with the law, but more about her conviction as an actual thief, since it was Paltrow who had been painted as a thief for years following the breakdown of their friendship.
In January 2015 Paltrow very openly denied the long-running rumour that she stole the script on The Howard Stern Show.
“I swear to God I did not, I’m raising my right hand on the Bible. I swear to God.”
Pop Culture Context
Interesting that Ryder never publicly addressed her friendship or fallout with Paltrow. The narrative has been shaped almost entirely through industry gossip, Paltrow’s later comments, and retrospective media framing (like this one), but never from Ryder’s own voice. For me, Ryder’s stoic (even aloof) silence is part of what keeps this story interesting.
If you know me, you know, that in most cases I’m not one for team this or team that. I’m more of a zoom in and zoom out person - just like I did with that actual photo of Paltrow and Ryder. All that to say, that I like many other pop culture obsessed commentators, need to look at every situation within its context.
Ryder found fame before the industry and society in general had a language or empathy for burnout, anxiety, and living under public scrutiny. Like so many other actresses, her fall was treated as entertainment rather than a call for help or a warning. Paltrow’s rise came slightly later, when reinvention and control of your own narrative was not only possible but became a business in its own right.
Lest we forget Paltrow’s many marvellous additions to pop culture from vagina scented candles to conscious uncoupling and, of course “I wish you well” in her very own court room drama – it was a beautiful time on the internet.
Paltrow denied, contextualised, and eventually reframed the narrative of the Shakespeare script rumour across platforms. Ryder said nothing. Silence, in celebrity culture, while is still a response, also leaves room for the rest of us to connect the narratives.
The Entertainment Value of Female Conflict
Hollywood in the 1990s and early 2000s was a pretty toxic place (not entirely sure how much has changed actually). The industry rarely made room for two women of the same generation to occupy equal space, even if they are friends. The system probably pushed them into competition, whether they wanted it or not, whether they were aware of it or not.
It’s a Hollywood, media, and society thing to mythologise female friendships and enjoy watching them fracture before they completely unravel. Elizabeth Taylor and Debbie Reynolds, Joan Crawford and Bette Davis, and more recently Blake Lively and Taylor Swift - it’s happened plenty of times before and will continue to happen. Keep an eye out on Ariana and Cynthia.
Also more recently, and virally, Ashley Tisdale wrote an essay for The Cut entitled Breaking Up With My Toxic Mom Group and the internet wasted no time linking Hillary Duff and Mandy Moore as part of said mom group with plenty of deep dive theories on what exactly happened. The story was so popular that studios are reportedly showing interest in adapting Tisdale’s essay into a film.
Again, here an example of the breakdown of female friendships, especially if they intersect with celebrities, churned out for entertainment informally through the news cycle and potentially now in a formal and scripted way. Studios understand, they know that conflict between women is a universal touch point that connects various facets of daily life that people can’t look away from.
Hello, we have a whole network and franchise based on this very premise, where the breakdown of close knit female friendships is packaged as entertainment, spawning countless of viral moments, memes, and catch phrases.
In the current season of Bravo’s The Real Housewives of Salt Lake City, in an episode entitled Out of Gas, spiritual leader of the Faith Temple Pentecostal Church, Mary Cosby, got into a tense moment with her close friend the hair stylist and entrepreneur Angie Katsanevas. Audiences, including myself, had enjoyed watching the two, who couldn’t be more different, become very close.
However, in the episode in question Katsanevas made a joke about Cosby’s flatulence to which Cosby insisted it wasn’t her who farted but that the fart belonged to Katsanevas’ dog. Katsanevas then insists that the fart is Cosby’s to which Cosby claims she can tell the difference between human gas and a dog gas. The exchange becomes a source of conflict between them, with Mary frustrated that something so small, and smelly, had affected their friendship so deeply.
Sad, Obsessive, Entertaining
The Real Housewives of Salt Lake City storyline, equally hilarious and absurd, is not that dissimilar to Paltrow and Ryder’s lore – in theory anyway.
Something private, whether issues of flatulence or someone being a “Vagina Ryder” or how a script found itself in someone’s hands, should remain within the confides of the friendship circle. Our obsession with the narrative of the step by step break down of female relationships is really quite sad and yet also so very entertaining for us to consume.
What in our consciousness, in some rabbit hole of Freudian theory, makes us wired to salivate over this particular genre of human folly is something I’m afraid will take generations of enlightenment to leave our collective systems - if at all. As for Paltrow and Ryder, judging from the photos, they look like they were having an amazing time. I love that for their younger selves - while I’m sure it was a good time until it wasn’t, they were at least, like most friendships that only last a season, there for each other in a way that matters and not playing out a role for all of us to consume.
I can't imagine Winona in that role, so I find it hard to believe the story!