Winona Ryder is a remarkable talent. She is still one of the best American actresses for entertainment that borders a bit on the quirkier side. She has re-established herself most recently with roles in Beetlejuice Beetlejuice and Stranger Things.
Ryder got her start in the 1980s with a decent role in Lucas, but she went on to become one of the most in-demand actresses in the 1990s. She was even wanted for The Godfather Part III for the role that eventually went to Sofia Coppola.
Never fear, Winona Ryder got to work with some of the most prolific filmmakers of her time, including Tim Burton and Martin Scorsese. While looking back at her career, it becomes crystal clear that Ryder’s darker side and impeccable style is perfectly in sync with the month of October and Halloween. How fitting that her birthday is just two days before Halloween?
Let’s take a walk down memory lane as we look back at some of her most famous (and best) roles.
1. Reality Bites (1994)
This comedy was a juggernaut from director Ben Stiller in 1994 as it presents the ideas of college graduates working in retail and raking up large sums of credit card debt. Reality Bites knew no topic it was afraid of tackling, and the film was way ahead of its time.
In Reality Bites, Ryder’s Lelaina Pierce is a college grad, a valedictorian of her university. She works at the GAP while rooming with some of her friends (Steven Zahn, Janeane Garofalo, and Ethan Hawke) from college.
Ryder is amazing in this part as her character falls into a relationship with Hawke’s Troy that ends up challenging her in very intriguing ways. It’s easy to see the trajectory of the plot, but not always easy to see how, exactly, these characters will end up in each other’s arms by the time the end credits come up.
Ryder becomes the voice of the audience, speaking for people who lived in the troubled 1990s where good jobs in desired fields were not easily attainable. In addition, the soundtrack (Lisa Loeb, U2, etc.) helped fuel the action in style.
Ryder never found a juicier role than the one she played in this picture.
One scene has Ryder and friends dancing to “My Sharona” in a convenience store, and Ryder is the one who appears to be having the most fun in this sequence. Garofalo tries to hog the spotlight — and she occasionally does — but Ryder is the one who is unstoppable in this masterpiece that speaks for the time period in which it was released.
2. Edward Scissorhands (1990)
This Tim Burton-helmed masterpiece surprisingly shows Winona Ryder as a blonde. Edward Scissorhands is, perhaps, Johnny Depp’s second most memorable role (Captain Jack Sparrow is certainly number one), and the story that transpires in this 1990 movie is beyond amazing in terms of the way it mixes romance, humor, and tragedy.
Burton’s fantasy welcomes Ryder’s sunny charm as her character, Kim, tries to help Depp’s character — who has scissors for hands — fit in. This is a movie where the leads fall in love despite their obvious differences, and Ryder gives it everything to make sure she is the most relatable one in the picture, which she ends up perfectly becoming.
Dianne Wiest plays the Avon saleslady and mom who brought Edward into her daughter Kim’s life. This movie is full of terrific energy all around, and Ryder complements Depp’s unintentionally humorous turn, making the picture a well-oiled machine full of snowy images and ice sculptures that Edward Scissorhands carves ever so well. This is Ryder’s best fantasy film and is a romance that broke hearts all over the world when it first released.
3. Beetlejuice (1988)
“Shake, Shake Senora” are the words in the song lyrics that everybody remembers from Beetlejuice. That Harry Belafonte song, “Jump in the Line” made Winona Ryder famous as she dances and shakes her body to it at the end of this earlier Tim Burton film.
Ryder’s character, Lydia Deetz, returns decades later in Beetlejuice Beetlejuice and continues to remind viewers of how wonderful she is in the first picture. Ryder’s keen sense of self is so evident in her work in the first Beetlejuice.
When the characters dance around the table in the original Beetlejuice, Lydia is an onlooker, not yet a participant. She seems intelligent as she is on to what’s going on in the haunted house the film sets itself in.
Ryder is perfect as her typical young girl character becomes fascinated by the world of the undead. She makes Beetlejuice a relatable story as Michael Keaton hams it up in the showy title role.
4. The Age of Innocence (1993)
If anybody doubted that Winona Ryder could truly act in an art-house film, The Age of Innocence proves Ryder’s former naysayers wrong. Ryder received an Oscar nomination for Best Supporting Actress, playing the original object of Daniel Day-Lewis’s affections in the film.
Martin Scorsese shows that he is able to obtain a wonderfully layered turn from the remarkable Ryder through the quiet moments in the picture where she lets her facial expressions and mannerisms help define her thoughtful character, May Welland.
Based on Edith Wharton’s complex, passionate story, Ryder excels in a part that few could believe the actress was capable of playing so well until seeing proved to be believing. Ryder actually gives Michelle Pfeiffer a run for her money in a film that is as moving as it is intriguing from the first minute Ryder appears on-screen until the last. This is one of her most nuanced, and most prestigious, performances to date.
5.) Heathers (1989)
Winona Ryder is at her most fascinating in Michael Lehmann’s Heathers. She plays Veronica Sawyer, a girl out to expose the “Heathers,” a mean girls-style clique at her high school. An accidental death occurs when one of the clique’s members is poisoned, and all hell breaks loose in a creative way that helped define the late 1980s’ dark independent cinema.
Ryder is paired with Christian Slater, who plays the vicious bad boy, J.D. Ryder and Slater seem to be cute together at first, but it is revealed J.D. is crazy beyond a reasonable doubt. In Jack Nicholson mode, Slater phenomenally brought out the best in Ryder in Heathers.
While Lehmann’s film seems too dark to please everybody, Winona Ryder’s performance is a true winner, revealing the actress at her most vulnerable in one of her first major roles. She’s the hero audiences want to root for, despite her quirks, and Ryder’s Veronica and J.D. face off in the film with results that will please any fan of creative dark comedy.
6.) Girl, Interrupted (1999)
Winona Ryder plays a depressed young writer, Susanna Kaysen, in Girl, Interrupted in such a way that it makes us forget everything we once thought we knew about her as an actress.
As Susanna gets to know other psych patients in the institution she is committed to, she seems more “normal” than she appears to be at the beginning the more the film goes on. Lisa, the Oscar-winning Angelina Jolie, and Daisy, the late, great Brittany Murphy, try to steal the movie from Ryder at key moments, and in Jolie’s case, it actually happens every so often, but in a good way.
Yes, Ryder takes second fiddle to these showy actresses with a nuanced, subtle performance that takes the film to unique and disturbing territory. Ryder nevertheless commands the audience’s respect and attention in this picture, which is one of the most moving portraits of the mentally ill ever made.
7.) Alien Resurrection (1997)
Winona Ryder got to play in a would-be blockbuster sequel, Alien Resurrection, and the results were quite interesting, to say the least. Jean-Pierre Jeunet helmed this film and managed to get a turn from Ryder that was unprecedented for the actress, who rarely took on big-budget movies.
Ryder plays Call, who the audience discovers is an undercover mercenary/android enlisted to help with the battle of the gooey Aliens that are typically fought by the one and only Ellen Ripley (Sigourney Weaver) in the earlier Alien films. Call is an interesting character that Ryder could play in her sleep, but watching her play this part with dark pizzazz and complementing Weaver’s fine work is nothing short of absolute fun.
This may not be a movie that Ryder will be universally loved in because, after all, she’s a robot, but she played the part so well, it ranks very high as a key role in her distinguished filmography.
8.) Mermaids (1990)
Cher, Winona Ryder, and Christina Ricci are the stars of the 1990 gem, Mermaids. It was Ricci’s first role and she was really good, but Ryder is the true star of the show, going as far as stealing scenes right out from under the Oscar-winning actress from Moonstruck, Cher.
Set in the 1960s, Ricci and Ryder play Cher’s character Rachel’s two daughters. Rachel is a single mom who finally shows her daughters a life they may really enjoy over the course of the picture.
Even “tough guy” Bob Hoskins appears for some funny moments in a movie that teeters on being both comical and serious, occasionally at the same time.
Ryder’s Charlotte is 15 in this movie, and Ryder plays her so convincingly that one will really believe in the character through all her trials and tribulations.
This is a movie that sells itself, but the fact that Ryder upstages Cher in some of the most profound scenes of the film is evidence enough of Winona Ryder’s tremendous talent.
9.) Welcome Home, Roxy Carmichael (1990)
In this movie, Welcome Home, Roxy Carmichael, where Ryder plays a young girl, Dinky, there is a real feel for small-town life, which is ably captured in the sweet picture from filmmaker Jim Abrahams.
This whole movie revolves around the return of a star who made it big and actually hailed from the small town the film is set in. Everybody is preparing for this woman’s return to her hometown. Her name is Roxy Carmichael.
Yet, the film becomes a story of Dinky trying to find herself as everyone around her is obsessed with the return of Roxy, including Roxy’s old boyfriend, played by Jeff Daniels.
You will never be the same after watching Ryder in this heartfelt, sweet, and moving movie. She proves she is more than capable of doing a coming-of-age story where she’s just a normal girl in many respects. Watching her find herself is a joyful experience.
Ryder’s best line in this little-seen movie is, “It’s good to want things,” and this movie is everything the audience could ever want.
10.) Little Women (1994)
Ryder portrays Jo March in this wonderful adaptation of Louisa May Alcott’s classic book, Little Women. Playing an aspiring author, Ryder adds dignity and respect to the part, making the audience care deeply for the life choices that Jo makes over the course of the story.
Gillian Armstrong directs Ryder here. It is a great combination of the acting and the crisp direction that makes Jo feel fresh in a way we’ve never seen her portrayed before.
Backed by the likes of formidable actresses such as Susan Sarandon, Claire Danes, and Kirsten Dunst, Ryder excels much more than anyone else in the picture. That’s because of the fact that Ryder can believably play a young woman from any time period so tremendously well.
It doesn’t hurt that Ryder actually looks like an aspiring author, which makes this extremely well-received part fit her like a glove.
11.) Mr. Deeds (2002)
This next film, Mr. Deeds, from filmmaker Steven Brill, is an example of Winona Ryder being a very good sport. Ryder had just gotten pinched for stealing clothes from Saks, and she was instantly labeled a “kleptomaniac” in the tabloids. Then, Mr. Deeds came out and made it all OK.
In the film, Ryder’s reporter character, Babe Bennett, goes undercover to get a “scoop” on the rich Mr. Deeds (Adam Sandler). If you think this is a typical Sandler vehicle, it’s not, and Ryder is the reason why. She creates believably humorous romantic chemistry with Sandler on-screen that makes this film fun with a capital ‘F.’
Besides the great, hilarious supporting work from John Turturro and a funny turn by Sandler, Ryder absolutely excels in the movie. She’s making fun of her situation as an alleged klepto — which was all over the tabloids back then — or maybe just really enjoying herself in this film, and the audience will simply love it if they sit back and “just go with it,” which is coincidentally another Adam Sandler film title.
Sandler and Ryder look like they had a blast making Mr. Deeds, and it shows.
12.) Boys (1996)
Boys is a great little find that received little fanfare — and undeservedly so. Staring with Lukas Haas in the film, Ryder portrays the very intriguing Patty in director Stacy Cochran’s tightly edited movie.
Patty is taken into a boys’ dorm room after falling off a horse. This movie is about the time Ryder’s character spends with Haas’s unique character, John, as the tension mounts surrounding when, exactly, she’ll be found by authorities. There are also flashbacks, which help explain Ryder’s character’s predicament.
This is simply a very interesting movie that Ryder fans may not know about, so it should be discovered to see her play a part that is much different from many of the others she has played throughout her career.
In conclusion, Winona Ryder continues to dazzle, and looking through all her films, there are certainly many other good ones to be found. What’s your favorite Ryder performance?
Thomas Duffy
Thomas Duffy is a Critics Choice member who has written film reviews for most of his life, starting at age 11 when he crafted his first full length movie critique on the film, "Roxanne," a Cyrano story featuring Steve Martin. As a result of that review and other movie obsessive writing, Thomas was awarded a creative writing award in sixth grade. Thomas is the proud author of nine books, including two highly acclaimed novels, "To Never Know" and "Social Work." Thomas can be found on X (formerly known as Twitter) or at a New York City movie theater watching the latest hit or independent movie. You can also run into him at Tribeca or at the New York Film Festival.