On Friday, Tim Burton’s Beetlejuice, Beetlejuice returns audiences to the now-beloved characters originally seen in the original 1988 macabre comedy. There’s a lot of love for this character (the recent Broadway show is a huge hit on the road), and everyone seemed to breathe a sigh of relief after positive word of mouth spread following its Venice Film Festival premiere. Stars Michael Keaton, Winona Ryder, and Jenna Ortega all received strong notices from festival goers.
While it’s always great to see Keaton on-screen, we here at The Contending are perhaps a little more thrilled to see Winona Ryder back on the big screen and returning to a role tailor-made for her. So, the excited got us thinking about her best performances. Maybe not always her strongest acting work, but her most memorable or culture-impacting work.
So, here we go with our Top 10 listing of the most iconic performances delivered by Academy Award nominee and Golden Globe-winner Winona Ryder.
10. The Simpsons: “Lisa’s Rival”
When you are asked to voice a character on The Simpsons, you know you’ve made it, and embodying a new character is big for your first television appearance. Ryder’s Allison Taylor becomes a thorn in our beloved Lisa Simpson’s side when she is transferred to Spingfield Elementary, and Allison’s strengths are almost identical to the Simpsons’ middle child. Is she not as special as she always thought? Ryder gives Allison a gentle hesitation in her voice, and I would argue that her voice talent has gone almost entirely unnoticed since this outstanding voiceover performance.
9. Friends: “The One With Rachel’s Big Kiss”
Winona had a hit-and-run relationship with television in the late 90s and early 00s. One of her very best cameo performances comes in the Friends episode “The One With Rachel’s Big Kiss.” Here, she plays Melissa, a former sorority sister of Rachel’s (Jennifer Aniston) with whom Rachel shared a drunken kiss. However, Melissa professes not to remember it at all. It may seem like no big deal now, but back then, it introduced a side of Aniston’s Rachel that no one ever imagined existed. In fact, that plays into Rachel’s frustration: she considers the moment one of the “wild and crazy” (ie – drunk college white girl) experiences she had in her life, and she cherished the moment for it. Ryder’s contributions here prove invaluable. She creates Melissa as a bubbly, brainless sorority sister, a perfect example of Ryder playing against type. She also completely nails one of her closing lines: “I don’t picture your face when I make love to my boyfriend.” It’s a fun performance that, back in the day, everyone was talking about.
8. The Plot Against America
Ryder’s last major television role came in the criminally underrated 2020 HBO limited series The Plot Against America. Based on the Philip Roth novel, the series imagines an alternate reality where Charles Lindbergh becomes president and steers America in a fascist direction. The role of Evelyn Finkel fit Ryder well and gave her much to chew on as she turns against her Jewish faith to embrace the fascist leanings of her lover, played by John Turturro. The series was mostly ignored by the Emmys, strangely enough since it premiered in the heat of the 2020 election, but Ryder received a Supporting Actress in a Limited Series or TV Movie nomination from Critics Choice for her work. The journey Evelyn undertakes is unlike anything Ryder’s ever done before, and at times, it threatens to overtake her. But she ultimately delivers a very strong performance that will, over time, be seen as some of her finest work.
7. Tie: Beetlejuice and Edward Scissorhands
It’s difficult to separate two of the three most formative Winona Ryder films, so we cheated and called it a tie! Both directed by Tim Burton, Beetlejuice and Edward Scissorhands helped form the persona of Winona Ryder that would inspire the obsession of millions. With Beetlejuice, she fully inhabits the goth-tinged Lydia Deetz with jet-black hair and a starkly white face (the pre-Christina Ricci, if you will). Her joy at the macabre events happening around her are, in a way, the gateway into Beetlejuice‘s bizarro world, and she works beautifully with Michael Keaton, Geena Davis, Alec Baldwin, and Catherine O’Hara. It’s no wonder she was so eager to return to the role in the upcoming sequel.
Edward Scissorhands takes her down a completely different path. She initially presents Kim Boggs as America’s sweetheart. The suburban girl next door. The nice and pretty blonde that every teenage misfit had a crush on. But Burton and Ryder change Kim Boggs’ trajectory, and she becomes intoxicated with the pathos of Johnny Depp’s Edward. Neither belongs in the other’s world, but they care deeply for one another. Put aside the regrettable old age makeup used in the framing devices and focus on the most iconic Ryder image to date: Kim dancing in the snow created by Edward slicing into an ice sculpture. It’s the most perfect image in any Tim Burton movie, and it solidified Winona’s star status.
6. Black Swan
Winona Ryder never really stopped working in the 2000s. After what was supposed to be HER MOMENT in Girl, Interrupted (a good performance totally overshadowed by Oscar-winner Angelia Jolie and the late Brittany Murphy, which is why it’s not on this list), Ryder aged into film after film that no longer seemed to understand who she was or what she could deliver. Gone were the days of the Burton-crafted object of obsession, and she found herself stuck in a near decade of uninspired roles, beginning with the atrocious Autumn In New York. In 2010 after appearing as Spock’s mom in the Star Trek reboot, director Darren Aronofsky seemed to play with Ryder’s rumored sense of being passed by and desperation. He cast her as Beth MacIntyre or “The Dying Swan” in Black Swan, starring opposite Oscar-winner Natalie Portman. Her performance is 100% camp but in the very best way. Ryder played into the rumors of her personal struggles and unleashed a tabloid-inspired, drunken, filthy-mouthed version of herself. And we’re all better for it.
5. Bram Stoker’s Dracula
In the midst of a reported nervous breakdown due to exhaustion in the early 1990s, Ryder turned down Francis Ford Coppola’s offer to play Michael Corleone’s daughter in The Godfather Part III. That role famously went to Sophia Coppola who was mercilessly and cruelly targeted for her performance. Would the film’s reception and reputation have been any different with Ryder in the role? One can only speculate… To make up for the absence, Ryder brought James V. Hart’s Dracula script to Coppola as a peace offering. She would star in the film as Mina Murray, the sexually repressed fiancee to Keanu Reeves’s Johnathan Harker. As a performance, this isn’t Ryder’s finest work. Her primness comes across as stilted at times, but she gives into Coppola’s inspired madness and opens up as Mina becomes infected with Dracula’s blood. Bram Stoker’s Dracula met mixed reviews upon release, but it’s now considered something of a minor classic in Coppola’s canon thanks to his inventive cinematic storytelling. I’m sure Ryder’s inspired delivery of the line “Take me away from all this… DEATH!” had something to do with that as well.
4. The Crucible
Nicolas Hytner’s acclaimed adaptation of the classic Arthur Miller play The Crucible was also supposed to be Winona’s Oscar-winning role. Here, she plays Abigail Williams, the vengeful child who incites the Salem Witch Trials after being rejected by Daniel Day-Lewis’s John Proctor. Looking back at her filmography, this role perfectly suited Ryder at the perfect time in her career. It allowed her to blend the outward-facing “nice girl” aspects of her persona with the darker, bitchier side we’d already come to love. She deftly navigated the line between petulant child and teenage temptress and expressed herself sexually, revisiting her Dracula days. And yet, the Academy didn’t care at all for the film, nominating only the great Joan Allen in the Supporting Actress category. Still, Ryder is excellent in stirring up the pre-pubescent rage that fuels the Salem Witch Trials and gives a wildly different performance than her previous outing with Day-Lewis, which we’ll talk about in a few.
3. Little Women
Before the Greta Gerwig days, Ryder starred in Gillian Armstrong’s take on the Louisa May Alcott novel. The role of “Jo” March fits Ryder’s range nicely, and she inhabits a period piece without a trace of stuffiness or anachronism. The Academy agreed: she received her second consecutive Oscar nomination, this time in the Best Actress category. I don’t have much else to say about Little Women. It’s been a long, long time since I’ve seen it, and I probably prefer the Gerwig version if I have to sit through it at all. Still, it’s a major milestone in Ryder’s career.
2. Heathers
Just after Beetlejuice, Winona Ryder delivered a star-making performance in the uber-dark teen comedy Heathers, directed by Michael Lehmann. Here, she again plays a basically good girl driven to evil acts for the love of a man. Ryder (a “Veronica”) and Christian Slater play teenage lovers enraged by the social cliques in their high school and murder several of the biggest offenders, staging their deaths as suicide. The film would NEVER be made today given the sensitivity around school shootings and teen suicide, but back in the 1980s, this was high comedy and razor-sharp social satire. This role ingrained Winona Ryder’s persona into millions of teenage girls who could see themselves in her. Ryder knew it would change her career as she offered to take the role for free as her agent begged her not to take it (reportedly on her knees). Ryder was right.
Her performance here gave her cooler street cred than she had before, and it introduced one of the most famous “he’s-so-hot-but-wait-he’s-psychotic” energies of all time with her relationship with Slater’s Jason Dean. Ryder’s Veronica goes from the Heathers’ untapped resource to being their biggest enemy, and Ryder yanks you along for the unpredictable ride. No one has pulled off a monocle as good as Ryder does.
1. The Age of Innocence
Winona Ryder received her first Oscar nomination and Golden Globe win (she was previously nominated for Mermaids, another high point in her career that just missed this list) came in Martin Scorsese’s period classic The Age of Innocence. Based on the Pulitzer Prize-winning novel by Edith Wharton, the film explores repression and social violence amongst the wealthy in New York’s Gilded Age. Ryder played the surface-level naive May Welland, fiancee and eventual wife to Daniel Day-Lewis’s Newland Archer. At first glance, Ryder’s performance seems incredibly stilted and one note. You’d think she doubled down on the innocence and naivety of the character, so much so that she appears to have little substance. But look closely… It’s all part of her plot. Later in the film, Ryder reveals May Welland to be the ultimate schemer, the one who orchestrates a massive plot (including lying about the timing of a pregnancy) to separate her husband from his true love — her cousin Ellen (Michelle Pfeiffer). Ryder’s Golden Globe win seemed to seal the deal with her Oscar nomination and potential win, capping off an incredibly successful late 1980s and early 1990s career run. But The Age of Innocence wasn’t nominated for Best Picture or Director, and Ryder received the only performance nomination. So, when she lost out to Anna Paquin for The Piano (Best Picture and Best Director nominated), it should have been no surprise. The loss still stings to this day.
Great list, Clarence. I’d forgotten Winona had such a respectable filmography. I made up a game after reading the headline, but not seeing your 10 selections. What would be my top 10, and would we overlap? I also had:
– Mermaids (a staple in our house)
– Lucas (I know, she was just a unknown supporting character, but it’s what came to me)
I did not have any of the television entries, which were very worthwhile. I LOVED her performance on Friends.