Few names in the realm of cinema resonate as deeply as Winona Ryder. Her beauty, seemingly unaffected by the passage of time, is matched only by her undeniable talent and mesmerizing on-screen presence. From her groundbreaking roles in the 1980s to her recent compelling portrayals, Ryder consistently delivers unforgettable performances that showcase her extraordinary range, unwavering versatility, and undeniable star power. Here, we’ll look at the best Winona Ryder movies.
10. Lydia Deetz – Beetlejuice (1988)
This fantasy horror comedy centres around the Maitlands (Alec Baldwin and Geena Davis), a pair of ghosts who begin haunting their own house and contact Beetlejuice (Michael Keaton) to help them scare away the new inhabitants of their home.
Winona Ryder played Lydia Deetz, the gothic teenage daughter and step-daughter of Charles and Delia Deetz, who discovers she can talk and communicate with the dead. Using her newly discovered abilities, she befriends the ghosts haunting her home and even offers to marry Beetlejuice to keep them around when her parents accidentally exorcise them. She’s a solemn yet kind girl who will do anything for her friends (evidenced by her willingness to marry Beetlejuice) and feels isolated from a world that doesn’t seem to see her no matter what she does. However, her love for the supernatural allows her to adjust to the sight of ghosts in her house relatively quickly, and her dark sense of humour will leave you chuckling at your screen.
The Stranger Things actress did an excellent job portraying Lydia, effortlessly playing the dark-looking, misunderstood girl with a soft spot in her heart for those who are as ignored or misunderstood as herself.
9. Kim Boggs – Edward Scissorhands (1990)
This cult classic, directed by Tim Burton, told the story of Edward Scissorhands (Johnny Depp), an ageless, unfinished humanoid with scissors for hands. He’s relatively harmless, but different events out of his control lead people in the small town to become mistrustful of him. The film plays out in a tragic, beauty and the beast-type story where neither side of the couple gets their happily ever after.
Winona Ryder played Kim Boggs. Though initially afraid of Edward because of his hands, Kim eventually realises that he’s actually a rather kind creation who does all he can to ensure that he is gentle with people and their friends. She defends Edward from her boyfriend, Jim, and falls in love with him and his kind nature. When he makes snow for her while carving an angelic ice sculpture modelled after her, she dances under it in awe of the beauty of the makeshift snow. After her ex-boyfriend lies to the townspeople about the danger of Edward and the blade-fingered humanoid runs away, Kim goes after him and confesses her love. After he kills Jim for hurting Kim, she lies to the townspeople to keep him safe from their wrath and goes home, never laying her eyes on her love again.
Years later, she tells her granddaughter the story of Edward Scissorhands, the man responsible for making the snow she occasionally dances under. Edward Scissorhands is definitely one of the best Winona Ryder movies.
8. May Welland – The Age of Innocence (1993)
Based on Edith Wharton’s novel of the same name and directed by Martin Scorsese, this film follows Newland Archer (Daniel Day-Lewis), a lawyer who plans to marry May Welland. Then he meets and gets to know Countess Ellen Olsenska (Michelle Pfeiffer), May’s cousin, who returned to New York after her disastrous marriage, and his feelings for May begin to change. He much prefers Ellen’s unconventional views on New York society to May’s lack of personal opinion and sense of self. Archer realises that he’s begun to fall for Ellen after she announces her plans to divorce her husband and rushes to marry May.
Winona Ryder did a fantastic job as May, the innocent yet shrewd wife of Newland Archer. Though she may be innocent, she isn’t blind. She knows that Archer is falling for her cousin and even asks if he’s rushing to marry her because he fears he may be marrying the wrong woman. As the film progresses, she learns to manipulate her husband, pandering to his sense of duty and the guilt that inevitably comes with falling for another woman. It all comes together at the end of the film when May admits to her son the truth of what she’d done to ensure her security.
She delivered such a strong performance that she was nominated for an Academy Award for Best Supporting Actress. Though she was lost, she later won a Golden Globe and a Southeastern Film Critics Association Award for the same category.
7. Charlotte Flax – Mermaids (1990)
Directed by Richard Benjamin and based on Patty Dann’s 1986 novel of the same name, Mermaids follows the adventures of Charlotte Flax, a neurotic teenage girl living with her wayward mother and younger sister in Massachusetts. The Flax family move every time Charlotte’s mother, Rachel (Cher), ends a relationship. During the film, Charlotte meets and begins to fall for 26-year-old Joe Peretti, a local school bus driver and caretaker of the convert, while Rachel meets and falls for Lou Landsky. After Charlotte kisses Joe while consoling him about the assassination of John F Kennedy, she flees, believing she is filled with sin and will be punished with pregnancy for what she’s done. She later learns that she can’t get pregnant via immaculate conception.
Over New Year’s Eve and Day, Rachel turns down a proposal from Lou and kisses Joe, angering Charlotte. Meanwhile, Charlotte dresses up as her mother, accidentally gets her younger sister, Kate (Christina Ricci), drunk and sleeps with Joe. Though things spiral out of control, with Kate almost drowning and Rachel slapping Charlotte for her irresponsibility, the Flax’s recover from the moment and bond in a way they have never bonded.
Winona Ryder did a brilliant job as the anxious, Catholic-obsessed Charlotte and received a National Board of Review Award for her performance.
6. Jo March – Little Women (1994)
Based on Luisa May Alcott’s novels Little Women and Good Wives, Gillian Armstrong directs this fantastic adaptation that follows the life and adventures of four sisters: Meg (Trini Alvarado), Jo, Beth (Claire Danes) and Amy (Kirsten Dunst and Samantha Matthis). As the girls grow, they deal with the trials of girlhood and the trails of womanhood, each handling them in their own way. They meet the “Laurence boy” (Christian Bale) next door, who they soon befriend and come to know as Laurie. They also make friends with his grandfather, who has a particularly soft spot for sweet Beth, and enjoy their quiet yet busy life while they wait for their father to return from war.
Winona Ryder does an excellent job as the head-strong and ambitious Jo, who cares deeply for her family and longs to be a successful writer. Jo took pride in thinking for herself and shunning the manners and fashion reserved for women, refusing to succumb to the pressure of society.
Her performance earned her a Faro Island Film Festival Award and a Kansas City Film Critics Circle Award for Best Actress. In addition, she was nominated for the same award at the Academy Awards, the Chicago Film Critics Association Awards and the Chlotrudis Awards.
5. Mina Murray – Bram Stoker’s Dracula (1992)
Directed by Francis Ford Coppola, this film follows the events in Bram Stoker’s 1897 novel. Years after becoming a vampire, Dracula (Gary Oldman) is visited by Jonathan Harker (Keanu Reeves), a solicitor who takes Count Dracula as a client and the fiancé of Mina Murray. Dracula sees a picture of Mina and believes her to be the reincarnation of his love and late wife, Elisabeta. Dracula leaves Johnathan in Transylvania so he can claim Mina for himself. He arrives in London, turns Mina’s friend Lucy Westenra into a vampire and attempts to charm Mina, who later leaves for Romania to marry Jonathan. Meanwhile, Quincey Morris, Dr Steward, Arthur Holmwood and Dr Abraham Van Helsing examine Lucy and decapitate her when she becomes a vampire. When Jonathan and Mina return to London, Dracula confesses to murder, and Mina admits she loves him, remembering Elisabeta’s life, and lets him transform her into a vampire. After tracking him back to Transylvania, Van Helsing, Jonathan, and Morris try to kill him, but they are stopped by Mina, who takes the dying count into the chapel, where they share a kiss, and he finally dies, reunited with his wife.
Winona Ryder was nominated for a Saturn Award for Best Actress for her performance as Mina. Bram Stoker’s Dracula is definitely one of Winona Ryder’s best movies.
4. Abigail Williams – The Crucible (1996)
This film follows the events of the Salem Witch trials as told through Arthur Miller’s play. While trying to conjure a spell that will kill Elizabeth Proctor so that Abigail William can marry her husband, John Proctor (Daniel Day-Lewis), with whom she was having an affair, a group of teenage girls are caught. To save themselves from punishment, the girls claim that Satan “invaded” them and accuse several innocent people of performing witchcraft, including Elizabeth, when they discover that the court will listen to them. What follows is a twisting trial of lies, accusations and false witnesses that eventually result in John being accused of witchcraft. People only begin to doubt Abigail’s work when she tries to claim that a minister’s wife is a witch, but by then, it is too late. John refuses to confess to crimes he did not commit and is hung for it.
Winona Ryder does an excellent job portraying the manipulative, John Proctor-obsessed Abigail, who manages to convince herself that she is the man’s true love and didn’t just take advantage of his insecurity during his wife’s illness. She is ruthless in her pursuit of John, not caring who has to die before she gets what she wants, but all her meticulous planning is for nought when John is condemned to hang.
Winona Ryder’s performance earned her a nomination for an Awards Circuit Community Award for Best Actress in a Leading Role and a nomination for an Online Film & Television Association Award for Best Drama Actress.
3. Lelaina Pierce – Reality Bites (1994)
This romantic comedy-drama directed by Ben Stiller follows aspiring videographer Lelaina Pierce as she films a documentary about the disenchanted lives of her friends and roommates and the challenges of their careers and lifestyle choices. Four friends who have recently graduated college live together in Houston, Texas and try to make lives from themselves. Troy Dyer (Ethan Hawke) is a coffee-house guitarist who has managed to lose several minimum-wage jobs, Lelaina is working as a production assistant, her roommate Vickie has an HIV scare after one of her one-night stands tests positive for HIV and Sammy Gray, Vickie’s friend, is gay. However, he has not begun a relationship with anyone because he doesn’t want to come out to his parents. After Leleina meets Michael Grates (Ben Stiller), an executive at an MTV-like channel, they start dating, and he wants to get one of the documentaries she’s working on to air on his network. Sammy and Vickie’s problems eventually work themselves out, as Vickie’s HIV test comes back negative, and Sammy comes out to his parents. Still, Lelaina has begun a downward spiral that starts with her losing her job and her relationship with Michael after she sees that he’s let his network compromise her artistic vision.
Winona Ryder did a fantastic job as Lelaina. This is probably because she enjoyed the script and felt connected to it, saying, “I think my character is very close to what I would probably have ended up as if I hadn’t become an actress.”
2. Susanna Kaysen – Girl, Interrupted (1999)
Based on Susanna Kaysen’s memoir of the same name, this psychological drama tells the story of her 18-month stay at a psychiatric hospital after a suicide attempt. After a nervous breakdown leads her to overdose on aspirin and alcohol, Keysen is sent to Claymoore, a local psychiatric hospital, against her wishes. While there, she befriends Polly “Torch” Clark (Elizabeth Moss), Cynthia Crowley (Jillian Armenante), Daisy Randone (Brittany Murphy), Georgina Tuskin (Clea DuVall), Janet Webber (Angela Bettis) and sociopathic and rebellious Lisa Rowe (Angelina Jolie). Rowe encourages Keysen to stop taking her meds and resist therapy and defends her by insulting the wife of a man Keysen had an affair with before her nervous breakdown. Finally, Randone is released, Keysen learns she has borderline personality disorder, and Polly has a breakdown that leads to her getting placed in isolation.
Keysen and Rowe drug a night watch nurse and try to comfort Torch by singing to her, and the two are punished in the morning, with Rowe having to endure electroshock therapy and solitary confinement. However, that night she breaks out of solitary and convinces Keysen to escape with her and the two travel to Randone’s newly rented apparent, where they bribe her with Vallium and learn that she has been cutting herself. The following day they find her dead in her bathroom, and a horrified Keysen watches as Rowe searches Rondone’s home and body for cash. She returns to Claymoore, and Rowe flees to Florida. However, she is apprehended just before Keysen is released and steals her diary to read for the amusement of the other patients. One of Keysen’s entries, where she expresses sympathy for Rowe being a cold, dark person, causes her to attack Keysen and break down when she confronts her.
Despite everything, the day Keysen is released, she visits Rowe, and the two reconcile. Winona Ryder’s performance got her nominated for the Blockbuster Entertainment Award for Best Actress; however, many felt that the movie itself was a poor reflection of the source material it was based on.
1. Veronica Sawyer – Heathers (1989)
This dark comedy follows the story of Veronica Sawyer, one of the girls in a very popular clique who misses her old life with her kinder, less popular friends. She becomes fascinated when the rebellious Jason “J.D.” Dean (Christian Slater) arrives at the school and pulls out a gun to fire blanks at bullies Kurt and Ram. Eventually, she begins a relationship with J.D. But, unfortunately, her world quickly spirals out of control. While trying to give Heather Chandler, the clique’s queen bee, a fake hangover cure that will make her throw up, Veronica accidentally gives her drain cleaner, which she thought J.D. poured into a mug as a joke. He then gets her to write a dramatic fake suicide note, and people worship her even more while the other two Heathers in Veronica’s clique use the suicide to gain more popularity.
After a double date with Heather McNamara, Kurt and Ram goes sideways, and the boys spread rumours about Veronica, ruining her reputation, J.D. proposes revenge. What Veronica doesn’t realise is the bullets she thought were tranquilisers are actually lethal. This leads Veronica to break up with J.D., but this doesn’t stop things from spirally further out of control. She fakes suicide to prevent J.D. from killing her and then stops J.D. from killing the entire school, though he does end up killing himself in the process. After everything, she reignites her friendship with her former friends.
Despite its dark nature, this Winona Ryder movie was well-received and eventually became a musical.
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What do you think are the best Winona Ryder movies?
