Winona Ryder has been making waves in Hollywood ever since her breakthrough role as Lydia Deetz in Beetlejuice in 1988. The role led to her whirlwind rise to fame as she went on to appear in some of the most memorable films of the 1990s, including Edward Scissorhands, Bram Stoker’s Dracula, The Age of Innocence, and Little Women. While she took a brief hiatus from Hollywood in the early 2000s, she returned to acting in 2006 and has been making her comeback ever since.
She has enjoyed success recently with her roles in Stranger Things, The Plot Against America, and Destination Wedding. Meanwhile, she’s also returning to her roots to reprise her role as Lydia for the first time in 35 years for the long-awaited Beetlejuice 2. With Stranger Things’ final season and The Haunted Mansion also on the horizon, the next few years are shaping up to be pretty big for Ryder, marking the resurgence she deserves. Here’s a look at 10 of her best TV/film roles over the years, ranked to the best.
10. Looking for Richard
Looking for Richard is largely a documentary on William Shakespeare and his play Richard III. However, it does feature scenes of Richard III performed by actors such as Ryder, Kevin Spacey, and Kevin Conway. Al Pacino portrays Richard III and also appears as himself to provide commentary on Shakespeare’s legacy. Looking for Richard gives viewers an inside look at what it means to translate Shakespeare’s works to film. The behind-the-scenes looks at making the play, Pacino’s energetic passion, and the educational aspects are quite fascinating and will keep viewers intrigued. However, it is a bit difficult to determine what the film is trying to say about Shakespeare or why it chose to frame its message in this manner.
9. Frankenweenie
Frankenweenie is a stop-motion animated horror comedy that follows Victor Frankenstein (Charlie Tahan), a young scientist who brings his beloved dog and best friend, Sparky, back to life. However, when his reanimation invention falls into the wrong hands, it leads to his hometown being terrorized by deceased animals turned into monsters. Frankenweenie is macabre, eccentric, and sometimes a little too chaotic with its monster mayhem, but the underlying story about one boy’s incredible love for his little dog is beautiful and heartwarming. The unique black-and-white stop-motion animation also adds melancholy, charm, and nostalgia to the film, and it’s a sweet homage to Mary Shelley’s Frankenstein. The film also reunites Ryder (who plays the neighbor girl Elsa Van Helsing) with frequent collaborator Tim Burton. It’s certainly not a perfect film, but it’s enjoyable and elevated by Burton’s and Ryder’s gothic flair and a heartfelt premise.
8. The Plot Against America
The Plot Against America is based on the novel of the same name by Philip Roth and explores an alternative American history where Charles Lindbergh (Ben Cole) wins the 1940 Presidential election and turns the country towards fascism, antisemitism, and xenophobia. Ryder stars in the series as Evelyn Finkel, a Jewish woman who falls for Rabbi Lionel Bengelsdorf (John Turturro) and is swayed to support Lindbergh as he does. The Plot Against America is a captivating but terrifying TV series that eerily parallels the political climate of today and warns of how quickly extremist opinions can take hold. It is a very slow build-up and teases audiences by framing its premise within a puzzle, but the reveal of the big picture is well worth the wait.
7. Black Swan
Black Swan is a psychological horror film that follows ballerina Nina Sayers (Natalie Portman), who is desperate to take over Beth’s (Ryder) spot as prima ballerina in Swan Lake after Beth is forced into retirement. However, when rival Lily (Mila Kunis) arrives on the scene, Sayers spirals out of control over the paranoia of being replaced as Beth was. Black Swan is a thrilling dive into the psyche of an anxious and obsessive competitive dancer, who will do anything to achieve perfection. Portman is absolutely captivating and intense in her role, which saw her win the Oscar for Best Actress. The film’s haunting themes of growing older, striving for perfection, and longing to make a legacy will remain with viewers long after it has finished. It can get a bit confusing and melodramatic at times, but it still manages to be emotional and thought-provoking.
6. The Age of Innocence
The Age of Innocence is a 1993 romantic drama directed by Martin Scorsese, based on the novel of the same name by Edith Wharton. The film follows Newland Archer (Daniel Day-Lewis), who is engaged to socialite May Welland (Ryder) but begins questioning their relationship when he finds himself attracted to the ostracized Ellen Olenska (Michelle Pfeiffer). The film takes place in the 1870s, which wasn’t a time of innocence, but of false appearances in which outward manners hid corrupt interiors. Hence, The Age of Innocence is a unique and satirical commentary on the period and the pressure to adhere to social norms. It also captures 1870s New York in exquisite detail with its costumes, makeup, and set designs. However, it does run a bit long, and not everyone will be appreciative of the period detail and sophisticated commentary.
5. Edward Scissorhands
Edward Scissorhands is a gothic fantasy romance by Tim Burton that follows the artificial humanoid Edward (Johnny Depp), whose inventor died before he could give him proper hands. He is taken in by the Boggs and quickly falls in love with their daughter Kim (Ryder), but struggles to find acceptance due to his appearance. Edward Scissorhands has a gothic flair with loads of eccentricity and humorous oddities. It has the feel of a dark modern fairy tale and illustrates the importance of acceptance as it rallies behind its gentle outsider. Ryder is delightful and elevates the heartwrenching love story as the youthful, gentle Kim. Edward Scissorhands isn’t Burton’s best work, but its strong message of acceptance, humor, and heart makes it very memorable.
4. Beetlejuice
Beetlejuice is a 1988 horror comedy from Burton that follows the recently deceased couple Adam and Barbara Maitland (Alec Baldwin and Geena Davis) as they try to rid their former home of its new inhabitants, the Deetz family. To do so, they employ the help of poltergeist Betelgeuse (Michael Keaton), realizing too late that they made a mistake by bringing this foul-mouthed, ill-tempered, con artist into an innocent family’s home. Beetlejuice is so outlandish and bizarre that it’s earned fan-favorite status as a cult movie. It’s fresh, humorous, and imaginative, and features phenomenal performances from Ryder as goth icon Lydia and Keaton as the vulgar Betelgeuse. Beetlejuice can be cartoonish at times, and while its underlying plot is eccentric and ambitious, it sometimes gets lost in the emphasis on visual effects and humor.
3. Stranger Things
Stranger Things is a sci-fi horror series that follows a group of friends who begin investigating supernatural happenings in Hawkins, Indiana after their friend goes missing. The show is a delightful tribute to the horror and sci-fi works of the ’80s, giving it a retro flair while blending science, the supernatural, and horror into an intriguing story. It is further elevated by its talented cast, including Ryder’s performance as Joyce Byers, the loving, intuitive, and kind mother who will do anything to protect her children. In addition to its intriguing premise, nostalgia, and powerful performances, Stranger Things is also a very poignant and charming coming-of-age story that captures friendships, relationships, and the trials and triumphs of growing older in a heartfelt and humorous manner.
2. Little Women
Little Women is a 1994 adaptation of Louisa May Alcott’s classic novel of the same name. The film follows the March sisters—Meg (Trini Alvarado), Jo (Ryder), Beth (Claire Danes), and Amy (Kirsten Dunst)—as they navigate young adulthood, romance, and illness while their father serves in the Civil War. The film is arguably the best Little Women adaptation of all time that beautifully captures the sentiments and spirit of Alcott’s beloved classic. It poignantly captures girlhood, womanhood, young love, war, and loss, as it follows four independent, ambitious, smart, kind, and strong women who demonstrate their importance in society. Also, there has never been a more perfect Jo than Ryder, who fully embodies her endearing tomboyishness, spirit, and humor and does justice to the most lovable March sister.
1. Heathers
Heathers is a 1989 black comedy that follows Veronica (Ryder), a high schooler who becomes disillusioned by the popular clique she’s part of. However, she quickly realizes violence isn’t the answer and attempts to stop her unhinged boyfriend, J. D. (Christian Slater), from killing all the popular kids at their school. Heathers is one of the best coming-of-age films ever made that turned the teen comedy genre on its head with its dark and satirical take on high school life. Subtly entwined in the shocking and dark premise are mature themes of teen suicide, prejudice, status, and conformity. Its themes and commentary on high school life still hold true today, and Heathers remains a brilliant and cynical masterpiece.
(featured image: Netflix / HBO / New World Pictures / Disney / Searchlight Pictures)
