Winona forever: Why the legendary Ms. Ryder deserves to be celebrated now and always

Anne T. Donahue and Peter Knegt each write regular columns for CBC Arts, and when they discovered they shared a love for Winona Ryder, they decided to join forces in honour of her 49th birthday.

Peter Knegt: So Anne, we are virtually gathered here to celebrate our mutual love for one Winona Ryder, who was born Winona Laura Horowitz on this day in 1971. And while we understand if anyone is wondering whether we confused the math and thought today was her 50th birthday, we are well aware it is actually her 49th. But this is 2020 and we a) need reasons to celebrate things and b) cannot be certain we, Winona and the world will exist come October 2021. 

Anne T. Donahue: And your understanding of this is exactly why it was crucial that we collaborate in this way. So to be completely honest, I was a late bloomer in terms of Winona. I've never seen Edward Scissorhands all the way through. I've only seen parts of Beetlejuice because I wasn't allowed to see it as a kid. But then I saw Girl, Interrupted in high school and it spoke to my angsty, emotional, teenage heart. Like Susannah Kayson (author of the book the movie was based on), I also felt sad and scared and completely out of control of my own life. And while I thought Lisa was cooler (because Angelina Jolie shines in this role), Susannah's vulnerability made me begin to identify my own. Which I think is something Winona does so well in her movies: she makes you feel exactly what she's feeling, even if you're desperate for her character to make better choices.

Like, hello, Reality Bites. I mean, I personally wouldn't spend hundreds of dollars on a psychic phone line, but it's shocking how even at 35, I can feel the way 23-year-old Lelaina Pierce is feeling, too. (Also, I have a big crush on Ethan Hawke, so this doesn't help, either.) Her characters are safe places on which you can project yourself, or the versions of yourself you wouldn't dare inflict on your friends or family. Also, I would've taken the job at the Gap, but that's another story.

What draws you to Winona? Is it her roles or is it her, as a person?

PK: I mean, both. But my initial draw was definitely just her. I was quite the opposite of a late bloomer in my love for Winona, in a fairly extreme way. The first time I ever saw her was when my parents took me to see Edward Scissorhands when I was six years old. I still vividly remember how immediately taken I was by her presence onscreen. There's something about her eyes, her voice that just made me feel ... safe? You could definitely read into the fact that in this specific film, she's basically an ultimate ally to someone society rejects, and as a young gay boy there was surely something inside me that took comfort in that. Either way, I walked out of Edward Scissorhands obsessed.

Within a year, I had rented every single one of the nine movies she'd made by that point (yes, I saw Heathers when I was seven years old) and my childhood bedroom was soon entirely adorned with Winona. I legit had a Welcome Home, Roxy Carmichael poster on my wall from 1991 to 1994. My mother just thought it was a boyhood crush, when in reality I think I wanted to emulate her. Even though my introduction to her was in arguably her most traditionally feminine role ever, there's something so non-normative about how Winona presents herself, especially in those early roles. And at that point she was also basically one of the most famous actresses in the world ... which just added to my adulation. 

I'm sorry, I feel like I've started things off a little Ryder or die on my end, but that's genuinely how it all started. And while I can't say my fandom has maintained its full fervour 30 years later, there's no celebrity I root harder for than her even today. Also you need to watch Edward Scissorhands all the way through, Anne!

ATD: I know! I know, I know, even if my dislike of Johnny Depp runs deep. I'll just pretend he's being played by someone else.

But I think your love of Winona is very beautiful. It's also a testament to her power considering we both felt safe to be ourselves when watching her movies, and the places we needed to feel safe most were so different. When I watched Reality Bites for the first time (at 23 — shameful, I know!) I felt so much less like a failure since I was also trying to find myself, had zero dollars to my name, and wanted so badly to be something more than I was. I don't even think I really understood that until the infamous Ethan/Lelaina exchange, "Honey, the only thing you have to be at 23 is yourself," because I didn't want to admit that I was not just planless, but also completely unaware of who I was.

I don't think anyone else could've played Lelaina, though. I mean, the entire movie is cast perfectly, but Winona makes her character so equally lovable and equally frustrating. Which is something I think she does so well, too: I've never seen her in a movie where she veers toward sainthood. She shines when she's complex, and she embraces that complexity. Even in Black Swan! Onscreen for minutes, and I think she outshines Natalie Portman.

How do you think she's evolved over the course of her career? Both in her performances and as part of what she shares of her personal self? I mean, to start, when I think about the shoplifting incident, I get angry because I don't think it would've sparked the backlash and hiatus it did in 2001. I mean, it was shoplifting! It's not like she went through someone's purse and stole their wallet.

PK: In your defence, I recently rewatched Reality Bites for like the 100th time (seriously, I'm not sure I've watched any movie more times), and I still related to Winona's Lelaina and all her decisions so much despite now being a full decade-plus older than that character. Also it never fails to startle me when I remind myself: Ben Stiller's directorial debut was Reality Bites.

As for the evolution of Winona? Look, it's hard to not wonder what a parallel universe where she wasn't assumingly pushed to such a brink would look like. From 2000-2009, basically her entire 30s, she made almost nothing worth noting save an animated performance in Richard Linklater's A Scanner Darkly. And surely that had a lot to do with both whatever was going on with her at the time of the shoplifting incident ... and the fallout from how the media ridiculously handled it (free Winona forever). But I do think the Winonassance has been underreported. And I don't just mean Stranger Things, which she's fine in but doesn't really have a lot to do. I've been most impressed by her work in David Simon projects like Show Me a Hero and The Plot Against America (the latter should have gotten her an Emmy and is by far the most underrated anything of 2020), her 2018 Keanu Reeves reunion Destination Wedding and her two episodes of Drunk History.

Obviously this is nothing compared to the run she had between 1988 and 1994 that arguably created one of the most impressive filmographies ever for someone under 25. But it does make it clear that Winona still very much has "it" — we just need more worthy projects to come her way. David Simon — one of the most brilliant minds around — clearly sees this too and I for one want him to build his next HBO series entirely around her. I mean, she's still only 49! We could have multiple eras of Winona awaiting us if Hollywood gets its shit together.

I'm curious though: what's your ultimate Winona performance ... and, conversely, has there ever been a performance that made you sincerely question your love for her? For what it's worth, my former answer involves Cher and my latter answer Richard Gere.

ATD: That's the thing! She's only 49! And if she were a man (and yes, I will absolutely go here), you know her storied history wouldn't be anything to come back from — she'd simply be Robert Downey Jr. instead. Hollywood doesn't know what to do when a female ingenue begins to grow up, begins to push back, or begins to walk the path of self-destruction most of us tend to wander down for at least a few years. And here we had Winona exhibiting the symptoms of being an actual person, so the industry and the media freaked out.

Embarrassingly, it took me a long time to realize that her trajectory wasn't something I personally needed to apologize for. Like, "Oh shit, what does it say about me that one of my favourite actors is stealing?" As if it were my own shortcoming that she, like any person, was struggling. As if I wasn't drawn to her characters because they were struggling! I bought hard into the belief that actors were supposed to be model citizens. And in the words of Natalie Portman in the best SNL sketch ever, "I never asked to be a role model."

And man alive, Richard Gere. I saw Autumn in New York in theatres with my best friend, and we both prepared ourselves for two hours of non-stop sobbing. Instead, we ended up making our own running commentary and planning what we'd do later that night, and nobody even yelled at us because I don't think anybody else was there. It was just such a forgettable film! It was so un-Ryder! Also, Richard Gere is over 20 years her senior. We were supposed to feel something for this union? We were supposed to cheer them on? This wasn't Stepmom, for heaven's sake. We were deprived of Ed Harris. Richard Gere is no Ed Harris.

What about you? And since I have you here, what type of role would you like to see Winona in next? Something developed by David Simon specifically? Maybe a character in the realm of McNulty? (A dream.) I think she plays soft and vulnerable so well, but you also need that ability to play a completely depraved hard-ass. That's my issue with Stranger Things, by the way: like you said, she has nothing to do! Justice for Joyce, people!

PK: Autumn in New York definitely represented some sort of Winona tide-turning in terms of the quality of roles she was being offered. It's a horrible movie, as were too many that soon followed. Remember she was reduced to being Adam Sandler's love interest in Mr. Deeds!? Or worse, Kevin James's in The Dilemma? Which is absolutely a symptom of how Hollywood has historically handled female ingenues past a certain age: they give them soulless roles opposite the leads of I Now Pronounce You Chuck and Larry. 

As for her future, I turn to what Winona herself seems to have in mind. Almost a decade ago, I had the lifelong dream of an opportunity to interview her in person when she was doing press at TIFF for the unfortunately not-very-remembered hitman biopic The Iceman (Ryder played the wife of Michael Shannon's titular "Iceman" — and it's neither a bad movie nor a bad Winona performance!). Although I am certain I frightened her with my initial declarations of superfandom (I may or may not have opened by telling her that when my mother found out I was gay, the first thing she said was, "But what about how much you love Winona Ryder?"), I did get a quote from her that I was really proud of:

"You have to make a life for yourself so that it's not all about this," she told me. "Life's short, so if you're going to spend months doing something, it's gotta be pretty special ... But I'm very happy to enter my Baby Jane years, and hopefully segue into the Ruth Gordon years."

And this is what I want, because I know it's what Winona wants: a Bette Davis/Joan Crawford/Ruth Gordon-era of Ryder where she just digs into a lifetime of challenging emotion to deliver iconic performance after iconic performance. Maybe it's a David Simon-directed series where she plays a McNulty-level complicated woman on the verge. Maybe it's this generation's Harold and Maude (opposite ... Jacob Tremblay?). But whatever it is, I just hope Winona feels like it's special. 

ATD: For the record, I am never to be reminded of I Now Pronounce You Chuck and Larry again. How dare you. But fortunately, the horrors of that memory have been washed away with that incredible Winona quote. Did you cry when she said it to you? I'd have wept, and begged her to hang out with me for the rest of the day and let her press junket go straight to hell.

I love, love, love the idea of Winona experiencing a resurgence that eclipses even the roles we associate with her the most. I want to see her exude the emotions she's always brought to her characters, but with the sage and wisdom of someone who's been through some real shit. I see her almost like Bette Davis when she played Margot Channing in All About Eve. Davis had always been this incredible powerhouse of an actor, but she elevated Margot thanks to her own experiences in the industry and her experiences in life. And, and, and: wouldn't it be amazing to see Winona treated like the force she is? Wouldn't it be incredible to watch her draw from over three decades of being terribly treated by the media and emerge in a starring role that very purposefully declares, "How dare you doubt me?" That's my dream. Also, for her to read this and be our friend. But I'll take the former over the latter if it makes Winona Ryder feel her best.

Queeries is Knegt's weekly column that queries LGBTQ art, culture and/or identity through a personal lens. Anne-iversaries is Donahue's bi-weekly column that explores and celebrates the pop culture that defined the '90s and 2000s and the way it affects us now. You can check out a few editions of both below.