But it wasn't Winona who got that awards-show glory. 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. 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. She was ‘his’ chosen starlet, cast in many of his films. Of course, she was likely to get it, since Harvey was among her biggest fans. But the deal wasn’t done and Gwyneth saw it, read it, and called her agent the next morning to say she wanted it. Winona was to play the female lead, the object of a young William Shakespeare’s love, Viola De Lesseps. And it was, as Hollywood lore goes, on Winona Ryder’s coffee table, waiting to be read. 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. 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. And all was well in the grungy old world of 1990s Hollywood. Gwynny and Ben and Matt and Winona were a double-dating superstar quartet. Gwyneth hooked Winona up with Matt Damon, while he was dating Minnie Driver. Listen to this episode of LowBrow, where Holly talks all about the Gwynny and Winona chronicles. And then, the best friends started dating best friends. They had matching pixie cuts, and they wore the same shoes. They sat on the floor at Hollywood parties together, ever-present cigarettes smoking in their hands. They held hands on red carpets and walked down New York streets with their arms around each other’s shoulders. But for a long, hot minute, they were inseparable. So if she and preppy New York private-school royalty Gwyneth seemed like an odd pairing, they were. Truly counter-cultural, while still holding enough mainstream appeal to open a family film – Mermaids, anyone? She was edgy and tiny and dark and acid king Timothy Leary was her godfather. Winona was the antithesis of the bouncy, blonde 80s bombshell actresses who came before. 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.īeetlejuice. She was being groomed for greatness.Īnd she was sharing an apartment with a woman who was already great. 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.
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.īrad Pitt was in her rear-view mirror. Gwyneth was a Hollywood ingenue, the Next Big Thing.
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.
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