Next month sees the arrival of the Netflix’s drama Stranger Things, a much-anticipated supernatural chiller about a missing boy, which pays homage to everything from Twin Peaks to Poltergeist and has been described by US critics as “looking like the show Steven Spielberg and Stephen King never made”.  It also marks the next, and perhaps most important, stage in Winona Ryder’s return to Hollywood’s spotlight. Now 44, Ryder has spent the past few years slowly rebuilding her career since it imploded in the early years of this century with a conviction for grand theft, shoplifting and vandalism amid rumours of prescription drug addiction. (She was subsequently sentenced to three years probation and ordered to undergo drug counselling.) Since then Ryder has taken a low-key approach to her career. There have been small but well-received roles in films such as Darren Aronofsky’s Black Swan, Rebecca Miller’s The Private Lives of Pippa Lee and Ariel Vroman’s crime thriller The Iceman. Last year she provided solid support as an ambitious but pragmatic politician in David Simon’s TV series Show Me a Hero.  In Stranger Things she takes a crucial role as the mother of the missing boy. It’s a solid part and one that makes great use of Ryder’s ability to be simultaneously steely and fragile. It also serves as a reminder of just how much impact Ryder had on the big screen in a relatively short space of time. At her best she had a rare emotional intelligence, the ability not just to overwhelmingly feel the part she was playing but also to make those watching relate to that emotion and believe it echoed their own.  In just five roles, all of them before she turned 20 – goth princess Lydia Deetz in 1988’s Beetlejuice, sarcastic former mean girl Veronica Sawyer in Heathers (also 1988), poetry-writing outsider Dinky Bossetti in 1990’s Welcome Home Roxie Carmichael, lovelorn cheerleader Kim in Edward Scissorhands (1990), and the emotionally conflicted Charlotte Flax in Mermaids (1990) – Ryder carved out her own distinct persona. She was the ultimate neurotic girl outsider, the black-clad antidote to every perky John Hughes heroine and the actress every angry teenager worth her smudged black eyeliner and Doc Marten boots claimed as her own. All successful actors have their shtick: Ryder’s worked because it wasn’t an act.  Born Winona Horowitz and raised in a commune in northern California, she was brought up in a bohemian world where her godparents included the 60s guru and LSD advocate Timothy Leary – “he took me to ball games, he made me do my homework; it was very, very protective and very fun,” she said in an interview in 2013. Beat poets Allen Ginsberg and Lawrence Ferlinghetti were also regular visitors.  Tormented at school for being different – “I wasn’t just bullied – I was straight-up beat up …I had six stitches and a fractured rib,” she told the Daily Beast last year – she grew up obsessed with the classic movies she watched on repeat. “They gave me a tingling feeling when I watched them,” she told Seventeen magazine at the height of her career. “I wanted to be part of them, even the ones with tragic endings.” Her other great obsession was the reclusive author JD Salinger. She has admitted to reading Catcher in the Rye more than 50 times – small wonder she could deliver Holden Caulfield-esque lines such as “Dear Diary my teenage angst bullshit has a body count” in Heathers with conviction and verve – and once told an interviewer that “Me and Holden are like this team”.  That ability to wear her most painful emotions so openly made Ryder’s early career. She had to fight for the lead in Heathers – writer Daniel Waters notoriously felt she wasn’t attractive enough – yet it is impossible to imagine any other actress pulling off that balance of furious, frustrated intelligence, self-mocking one-liners and the hungry need for the world to prove itself better and stop letting her down.  Yet the very ambivalence towards acting that made Ryder so intriguing to watch was also the thing that all but destroyed her career. “I always just really wanted to be a good actress,” she told the Daily Telegraph in 2014.  “Fame can be incredibly isolating … there was a time when I would go for a hike and I wouldn’t even know that I was being photographed. It was actually pretty weird and traumatic. I was so young that I didn’t understand what was going on.”  Dating Johnny Depp, whom she first met in 1989 when he was 26 and she was 17, didn’t help matters. By the end of that year they were engaged. Depp had Winona Forever tattooed on his arm (later amended to Wino Forever), and Ryder was part of the hottest, wildest and most whispered about couple in town. “When I was young I was the sweetheart of the press,” she told Harper’s Bazaar in 1990. “Then I became engaged to Johnny and it’s been bad ever since.” (She has maintained a discreet silence about her one-time fiancé’s most recent bad press).  At the time, though, the romance with Depp only added to her mystique, fuelling the sense that she was Generation X’s very own grunge princess, the prototype manic pixie dream girl, complete with much-imitated pixie cut. By 1993 the engagement was off and Ryder began a series of high-profile romances with musicians (alongside Salinger and movies, music was her third great love). She was rumoured to be the inspiration for everything from Ryan Adams’s Cry on Demand to Beck’s Lost Cause, and Courtney Love supposedly joked that “you’re no one in music until you’ve feuded with me or slept with Winona”. The 1994 film Reality Bites even tried to parlay Ryder’s brand of thrift shop cool into a hymn for the grunge generation, with mixed success.  As everyone scrambled to pin down her appeal, Ryder herself appeared increasingly reluctant to play the fame game. Having worked relentlessly throughout her teens, she’d dropped out of The Godfather III in 1990 amid talk of exhaustion, and in 1997 took two years off after filming Alien: Resurrection, claiming later that she hadn’t read any scripts she enjoyed. The few interviews she gave around this time hint that she felt increasingly torn between that desire to be “a really good actress” and a hatred of the celebrity-celebrating flipside of the dream.  All of which might explain why Ryder faltered when she should have soared. Her Oscar nominations – for The Age of Innocence in 1993 and Little Women the following year – were already long in the past by the time of her 2001 arrest. Her smart, unshowy turn in 1999’s Girl, Interrupted, a film she’d also produced and with which she strongly identified, was overshadowed by Angelina Jolie’s more obvious fireworks, and the movie that partially led to her downfall, the dire Mr Deeds, was mauled by critics. (Ryder broke her arm during the filming and would later date her painkiller issues to that time, telling Vogue in 2007: “I was taking [stuff] at first to get through the pain. And then there was this weird point when you don’t know if you are in pain but you’re still taking it.”) By the time of her 2002 trial with its Free Winona T-shirts and attendant hoopla, Ryder was already yesterday’s news.  Had she been a man, it might have been different. There is a certain leeway granted to male stars, a sense that boys will be boys and we all make mistakes. A Robert Downey Jr can fail time and time again but when he dries out and dusts off the charm the big roles will still be waiting. When a female star falls, she lands on stonier ground.  With that in mind, it’s no surprise that Ryder has never quite returned to the stellar heights of her teenage years. In Black Swan her jagged turn as a ballet dancer forced to confront the death of her career as a new star rises ensured that our nostalgia for what might have been reaches uncomfortable heights. The casting of the similarly big-eyed and fragile Natalie Portman in the younger role only rams the point home.  It’s hard too to escape the feeling that those memorable early performances were just too unusual and too good. That, like her hero Holden Caulfield, Ryder suffers from the question: what really happens to the angst-ridden teen malcontents when they have to grow up?  Salinger’s short stories suggest that Caulfield went missing in action in the second world war, then simply disappeared. Ryder too performed her own disappearing act. Here’s hoping that the smart and addictive Stranger Things provides a welcome new act for an actress who has always walked her own path.  Stranger Things is on Netflix from 15 July
As the 80s star of Beetlejuice and Heathers returns with a plum role on Netflix, we chart her troubled career