Winona Forever

Looking at some of the less celebrated Ryder turns in honor of the actress’s big screen return

One of the more under-the-radar indie releases recently has been writer/director Victor Levin’s offbeat romantic comedy Destination Wedding. Starring an intriguingly-paired Keanu Reeves and Winona Ryder, the film tells the story of a couple of jaded singletons who journey to the wine country for the wedding of their exes where, naturally, sparks fly. It’s an oddly appealing follow-up to Levin’s debut feature, 2015’s 5 to 7, a light drama which touched on an unorthodox, yet passionate romance between a young man (Anton Yelchin) and a French diplomat’s wife (Berenice Bejo), providing one of the most moving and refreshing comments on love the screen had seen in quite a while. Destination Wedding continues the trend of Levin’s unique take on love as his two leads are shown constantly rebuffing not just an obvious attraction to one another, but the concept of love in general. While response to the film has been mixed, the re-teaming of two such unconventional rom-com leads in a film aiming to dance around genre conventions is one of the more fitting ways to say goodbye to the summer movie season.

The release of Destination Wedding can’t help but remind me that its been a good long while since audiences have gotten to see Winona on the big screen. These days, Ryder has more or less limited her work to television, finding some of her best recent parts on television productions such as the BBC TV movie Turks and Caicos and the acclaimed HBO miniseries Show Me a Hero, before having one of the biggest career resurgences enjoyed by any actress over 40 with her breathtaking work as the loving and determined mother on Netflix’s Stranger Things.

Most of Ryder’s fans surely remember the ascent of Winona Ryder. Her era-defining performance as the disenchanted Veronica Sawyer in Heathers combined with her stint as Tim Burton’s early muse led to a kind of stardom no one would have predicted. There has always been something special about the un-cookie cutter Ryder who seemed to operate on her own acting orbit, while also managing to fit perfectly into any on-screen world she found herself in. It’s because of specialness that she could hold her own against Cher in the mother/daughter dramedy Mermaids, help Francis Ford Coppola realize his operatic take in Dracula (although I still weep at her having to bow out of The Godfather III, imagining what she could have brought to the film), profess her love for Daniel Day-Lewis in The Age of Innocence, become the face of Generation X with Reality Bites and bring the supposedly unfilmable Girl, Interrupted to the screen.

It’s a shame Ryder’s public troubles gave way to a pre-emptive hiatus in the early 2000s since at the time she was still an A-list actress who had enjoyed a bona-fide hit starring opposite Adam Sandler in his remake of Mr. Deeds. To get a grasp of Ryder’s star power, numerous mentions were made in the press about how the poster for Mr. Deeds was the first one in years not to feature the actress. But her much-publicized court case resulted in a loss of position within the industry, not helped by Ryder’s supposed shunning of high-profile studio films. The actress would regain some recognition and popularity in 2009 thanks to brief but memorable turns in both the Star Trek reboot and Darren Aronofsky’s acclaimed Black Swan before once again becoming a household name several years later when the Stranger Things craze hit.

When the glamorous, mysterious figure seen sauntering around her luxurious dressing room, with her face carefully hidden, in this past spring’s L’oreal commercial turns out to be Ryder, fans of the actress found themselves overcome with joy as the words: “Everyone loves a comeback” flashed on the screen. But Ryder never truly went anywhere. After the headlines and in between the “comebacks,” Ryder continued to carve out interesting characters for a collection of eclectic filmmakers, all of which solidified how much she’s able to bring to any project she’s in. Here’s a handful of some of those great performances audiences might have missed from one of the screen’s most unclassifiable, yet compulsively watchable actresses.

Simone (2002)

While the entertainment world awaited the result of Ryder’s legal matters back in 2002, they missed out on a delicious supporting turn in what remains one of the actress’s most uncharacteristic roles. Andrew Niccol, the mind behind Gattaca and The Truman Show, wrote and directed this understated, but potent Hollywood satire about a washed up director (Al Pacino) who designs a digital actress in a bid to keep the plug from getting pulled on his failing movie, turning his creation into a star in the process. Although Ryder’s role is only three scenes long, she dominates all of them as Nicola Anders; a pampered A-list actress who walks off the set of the movie in question because her trailer isn’t tall enough. The role may sound like caricature, but Ryder takes it to a real level, playing Nicola as someone who firmly believes in the self-entitlement she exhibits without ever having to chew scenery. It’s because of this that when a humbled Nicola turns up again midway through Simone (as a result of being dethroned by the digitized starlet), the effect of Niccol’s vision and the versatility of Ryder’s skill is more than felt.

A Scanner Darkly (2006)

It not only seems appropriate the Richard Linklater should direct sci-fi lit master Philip K. Dick’s most personal novel, but that he should also choose Ryder as the film’s leading lady. In A Scanner Darkly, Reeves plays an undercover cop who gets lost in a hallucinogenic mind trip while investigating the sudden presence of a dangerous futuristic drug known as Substance D. The film, with its loose narrative and mesmerizing rotoscope animation, is the definition of a cinematic mind trip. While praise for Reeve’s committed performance as well as the craze-filled ones by Robert Downey Jr. and Woody Harrelson, is earned, the brilliance of Ryder’s work shouldn’t once be underestimated. As Donna Hawthorne, the actress ends up giving A Scanner Darkly its most affecting and layered performance as both a pathetic druggie under a spell and a futuristic femme fatale utilizing her femininity. Eventually, when the final revelation of her character comes to light, Ryder plays it in such a way that the heft and depth of her past scenes only grows stronger and takes an already otherworldly tale even further.

The Informers (2009)

From one postmodern author to another. Ryder entered the world of Bret Easton Ellis when he adapted his own collection of short stories based on the loosely-connected lives of Los Angeles denizens in the early 1980s. In The Informers, Ryder plays news anchor Cheryl Moore, who is dealing with both aging on TV and a crippling relationship involving a married studio executive (Billy Bob Thornton). Although The Informers was whittled down to a critically reviled 98 minutes from it’s more sprawling (and supposedly involving) initial cut, the essence of Ryder’s work remains in tact. Watching her inhabit a woman who suddenly discovers the inescapable, hellish aspects of a life which on the surface seems ideal, is just the kind of internal character conflict the actress manages so well. One scene in particular sees Cheryl looking for privacy and momentary solitude at a local diner only to end up the butt of a cruel joke at the hands of a group of 20-somethings. It’s a sad moment featuring a woman the world sees as disposable and made all the more compelling thanks to the empathy Ryder shows her.

The Dilemma (2011)

Ryder took on a rare villain role in this lighthearted, but earnest, Ron Howard comedy starring Vince Vaughn as a man who discovers his best friend’s wife (Ryder) is having an affair, leading him to question whether or not he should tell him. On paper, Ryder’s Geneva reads like a figure to loathe; and in a sense, she is. The character threatens Vaughn’s Ronny with blackmail to the point of silence, but also gives a hint that there’s something sad and troubled about the marriage she’s in, leading her towards the decisions she’s made. The Dilemma also gives Ryder a chance to show her adeptness at comedy. For so long the image of the actress has been one of introspection, torment and ponderousness, leading her to be cast in a handful of worthwhile dramas and generally dark roles. But Howard makes fine use of Ryder’s gift for subtle humor and gives her a good handful of moments to play opposite Vaughn. Watching the latter’s manic energy mix well with the former’s gift as a solid comic straight man gives the film a genuinely enjoyable feel. The Dilemma may not be top tier Howard, but it’s a thoughtful comedy that’s only elevated by Ryder’s presence.

Frankenweenie (2012)

The long-awaited reunion between Burton and Ryder finally happened in the form of 2012’s criminally underrated Frankenweenie. Based on an early Burton short film, Frankenweenie used black and white stop motion animation for this tale of a young boy named Victor Frankenstein, who uses 1950s electricity to bring his beloved dead dog Sparky back to life. As the shy Elsa Van Helsing, Ryder perfectly gave voice to the oftentimes melancholic loneliness of childhood; a sentiment no doubt shared in real life by both her and Burton. Ryder’s choice to play the young character in the actress’s own adult voice was a stroke of brilliance. The result showed the underestimated level of maturity and perception within children, while at the same time showing how such complex childhood feelings and emotions, including alienation and insecurity, have the ability to continue into adulthood. Beetlejuice and Edward Scissorhands may have played large parts in making both Burton and Ryder household names, but Frankenweenie is every bit deserving of love and acclaim from both their fanbases.

The Iceman (2013)

Even when saddled with the typical “wife” role, Ryder manages to make her character come to life. That’s certainly the case with the actress’s work in The Iceman, where she took on the part of Deborah Kuklinski, wife of Richard Kuklinski (Michael Shannon) in the true life story of the country’s most notorious contract killer. As a film, The Iceman is a dark experience, going even harsher than its logline would suggest, with brutal violence and a quietly monstrous Shannon at the wheel. Into this gritty world is Ryder’s Deborah; a woman who let herself be charmed into a marriage, the majority of which she spent convincing herself was a fairytale until she could no longer avoid her suspicions. In what ends up being a darker variation on her Age of Innocence character, Ryder reaches a level of haunted not seen in her previous work. “There ain’t nothin’ to be afraid of,” Richard tells Deborah when there daughter ends up in the hospital as a result of a message sent by his enemies. With a mix of anguish and blackness, Deborah looks at the man she thought she knew and replies: “I didn’t know I was supposed to be afraid.”

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