Winona Ryder and Gwyneth Paltrow were best friends. Until they really, really weren’t.

It’s a vision hard to conjure as she sits in a Park City courtroom, modelling ski-resort true-crime chic that’s spawned a thousand memes, but once, Gwyneth Paltrow was cool. 

It was the mid-1990s. Gwyneth was a Hollywood ingenue, the Next Big Thing. The vagina candles, jade eggs and starvation diets were all decades away on a far horizon, and Gwynny was bar-hopping in leather pants, drinking cocktails, smoking cigarettes and dating the hottest actors in Hollywood only to dump them, leaving them longing. 

Brad Pitt was in her rear-view mirror. Ben Affleck, one half of celebrated ‘lil writing duo who was making Good Will Hunting, was becoming her new Thing, and Gwyneth’s star was on the rise. Seven. Emma. Sliding Doors. She was being groomed for greatness. 

And she was sharing an apartment with a woman who was already great. 

Just as it’s a little jarring to imagine Gwyneth as a club hopper with a smoker’s cough, if you’re only familiar with Winona Ryder as the kooky, slightly hysterical Joyce Byers of Stranger Things, you might struggle to understand how untouchably cool she was in the 90s. 

Gwyneth and Winona attending a premiere together. Image: Getty.

Yes, she had dated Johnny Depp (if this story is beginning to feel like a long list of problematic people, just wait until Weinstein appears), but the Queen of Slacker culture was entirely her own creation. 

Beetlejuice. Heathers. Reality Bites. Winona was the antithesis of the bouncy, blonde 80s bombshell actresses who came before. She was edgy and tiny and dark and acid king Timothy Leary was her godfather. Truly counter-cultural, while still holding enough mainstream appeal to open a family film – Mermaids, anyone?  

So if she and preppy New York private-school royalty Gwyneth seemed like an odd pairing, they were. But for a long, hot minute, they were inseparable. 

They held hands on red carpets and walked down New York streets with their arms around each other’s shoulders. They sat on the floor at Hollywood parties together, ever-present cigarettes smoking in their hands. They had matching pixie cuts, and they wore the same shoes. And then, the best friends started dating best friends. 

Listen to this episode of LowBrow, where Holly talks all about the Gwynny and Winona chronicles. Post continues after podcast. 

Gwyneth hooked Winona up with Matt Damon, while he was dating Minnie Driver. Gwynny and Ben and Matt and Winona were a double-dating superstar quartet. And all was well in the grungy old world of 1990s Hollywood. 

Until. 

There was a film that had been kicking around Hollywood for years, with a buzz that would rise and fall depending on whose name was attached: Julia Roberts, Daniel Day Lewis… It was Shakespeare In Love, and it had Oscar written all over it. The hype was due to its pedigree – it was written by Tom Stoppard it was going to be produced by Harvey Weinstein, who was running hit-factory Miramax. 

The script was one everyone wanted. And it was, as Hollywood lore goes, on Winona Ryder’s coffee table, waiting to be read. Winona was to play the female lead, the object of a young William Shakespeare’s love, Viola De Lesseps. But the deal wasn’t done and Gwyneth saw it, read it, and called her agent the next morning to say she wanted it. Of course, she was likely to get it, since Harvey was among her biggest fans. She was ‘his’ chosen starlet, cast in many of his films. In the later, reckoning years Gwyneth would say she was scared of Weinstein, and that after Brad Pitt confronted him for trying his criminal menace on her, he left her alone, leaving her in fear he would fire her.  

Gwynny got the role, Winona did not. 

And Gwynny won an Oscar for it. 

It shouldn't have mattered, because Winona was in the other hot film of that period, Girl Interrupted, and playing a fragile woman with mental health issues was exactly the sort of thing Oscar favoured. But it wasn't Winona who got that awards-show glory. It was Angelina Jolie, who was immediately flung into Hollywood-history-altering stratospheric fame. 

And Winona and Gwyneth weren't friends anymore. 

In the years that follow, Gwyneth moves to London. Marries a Coldplay. Becomes a domestic, macrobiotic goddess, and eventually starts a blog, called Goop. 

And she has a new best friend, called Madonna. And suddenly it’s Gwyn and Madge being papped on the streets in matching activewear, holding each other’s hands at awards shows and sharing a passion for dance workouts that whittle you away to nothing, courtesy of Tracey Anderson. 

And Winona? Well, things got difficult for her. 

In 2001, she was arrested for shoplifting at ladies-who-lunch department store Saks. A security guard said they saw her cutting off tags in the changing room, and that she took 20 items through the checkout while only paying for four. 

Winona would later say that she was under the influence of prescription pills she had become dependent on, but no matter. The headlines were brutal: 

"Reality Bites for Winona." ... "Ryder's Age of Innocence Over." ... "Winona Scissorhands." 

She was the butt of every joke with her mug shot on every talk show. 

Of course, you could also buy the now iconic Free Winona T-shirts in this new place called Online, but the infamy curse had set in. 

Winona Ryder in a Free Winona t-shirt. Image: British Vogue. 

It took years for Ryder to truly return to the Big Time. Which may well have been her choice, after years of making smaller choices. “I definitely retreated,” she told Harper's Bazaar. “I was in San Francisco. But I also wasn’t getting offers. I think it was a very mutual break.”

The last twist in the Winona-Gwyneth melodrama came in an early salvo from Goop. Before it was a mega e-commerce play worth $250m, Goop was a newsletter Gwynny would send out from her London kitchen. Full of recommendations of fancy things via her fancy friends. 

And in 2009, she sent one about why it feels so good when bad things happen to people you don’t like. 

If you believe that this blind Goop item is about Winona, which almost everyone does, it suggests a different side to the script-swiping break-up story.

Gwyneth 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. There went the high road."

If you’re still reading and wondering why, let’s just clear this up. 

In 2015, Alana Massey wrote an article for Buzzfeed about “Being a Winona In A World Made For Gwyneths” and it stands up strongly to a modern reading. 

In it, Massey writes: "My 'Winona in a world made for Gwyneths' complex is a theory that positions these one-time best friends as two distinct categories of white women who are conventionally attractive but whose public images exemplify dramatically different lifestyles and worldviews. One lives a messy but somehow more authentic life that is at once exciting and a little bit sad. The other appears to have a life so sufficiently figured out as to be both enviable and mundane. Gwyneth Paltrow is, of course, the latter.”

There it is. 

Are you a Winona, or A Gwyneth? You can apply this anywhere. 

At the School gate, the Gwyneths have a basket of sugar-free muffins and are hooking everyone up with the good doctor who can fix their hormone issues. 

The Winonas were late to drop-off and their children definitely forgot their hats. 

At the office, the Gwyneths have the hierarchy pegged from Day One and are well on their way to managing-up their way to C-Suite.

The Winonas are struggling with small talk in the kitchen but really want you to hear about the deeply interesting new project that could change the company’s trajectory for the better. If only they could figure out how to build a presentation deck. 

The Gwyneths have made their “no-go” lists for dating apps and they are sticking to them religiously, no matter how dreamy the bedroom eyes on that person holding the fish. 

The Winonas are still dating that arty type who flakes out on her every time she needs them, but who makes her laugh and gives great afternoon orgasms. 

And so to recap: A friendship break-up for the ages. A couple of female archetypes to beat ourselves with, and some excellent blind gossip. 

Hayley and Selena, this is what we want from celebrity feuds. Get your shit together, new-gen celebrities.

Image: Getty + Mamamia.