The undisputed queen of quirky and cutting edge roles, cinema darling Winona Ryder is famous for her diverse and colorful acting catalog and portrayals. Having been a constant force in the entertainment industry since her 1986 film debut at the age of 15, the actress has gone on to establish herself as a dynamite performer and incredibly gifted leading lady. The star made a name for herself in the late ‘80s, taking on peculiar and memorable parts in classic films like Heathers and Tim Burton’s Beetlejuice before gaining further prominence with major roles in Edward Scissorhands, Bram Stoker’s Dracula, and Little Women. Ryder has worked with a slew of highly esteemed directors including the aforementioned Tim Burton, Martin Scorsese, Francis Ford Coppola, and Darren Aronofsky.
The dynamic performer survived a brief career slump and subsequent break in the early 2000s, returning to the silver screen with roles in acclaimed pictures like Black Swan, The Iceman, the animated Burton flick Frankenweenie and The Experimenter. Ryder once again garnered widespread attention and critical acclaim for her dynamite portrayal of Joyce Buyers in the Netflix sci-fi horror series Stranger Things; the show earned numerous accolades and its fourth season is set to premiere sometime this year. These are the best Winona Ryder movies, ranked.
9 The Crucible
Based on the Arthur Miller play of the same name, 1996’s historical drama The Crucible chronicles a group of teenage girls who get caught conjuring love spells in the woods and are put on trial; they subsequently attempt to pass blame by accusing several others of witchcraft. Winona Ryder stars as a fictionalized version of Abigail Williams, who was one of the first people to falsely accuse their neighbors of witchcraft in 1692, ultimately leading to the Salem witch trials. Co-starring one of cinema’s finest actors, Daniel Day-Lewis, The Crucible failed to make it big at the box-office but received widespread acclaim by critics who praised the dynamite performances of its gifted leads. TIME magazine specifically praised Ryder, having written, “Her cheeks flush, her winsome beauty seared with erotic rage, Ryder exposes the real roots of the piece. Forget McCarthyism; The Crucible is a colonial Fatal Attraction.”
The 1990 family dramedy Mermaids follows a free spirited single mother and her two daughters as they relocate once again to a small Massachusetts town in 1963, where their familial bond is both strained and strengthened in their new home. Appearing on-screen with Cher, Christina Ricci, and Bob Hoskins, Winona Ryder portrays the neurotic Charlotte Flax, a girl who has grown weary by her mother’s wayward ways. Mermaids had originally cast Emily Lloyd for the role, but Cher complained she did not look enough like her daughter and recommended Ryder after seeing her in Heathers. The actress stole the show as Charlotte, garnering rave reviews for her charismatic and tender portrayal of the disillusioned daughter. The New York Times proclaimed, “Miss Ryder is so good, in fact, that “Mermaids” might have dared to be a tougher, more stylish movie than the stylish sitcom it is.” For her performance, Ryder was nominated for the Golden Globe Award for Best Supporting Actress and won the National Board of Review Award in the same category.
7 The Age of Innocence
An adaptation of the Edith Wharton novel, Martin Scorsese’s 1993 historical romantic drama The Age of Innocence features Hollywood heavy hitters Daniel Day-Lewis, Michelle Pfeiffer, and Ryder, and recounts the tale of a young lawyer who falls in love with the cousin of the woman he’s engaged to marry. All three of the lead actors were Scorsese’s first choices for the parts, and they each shined beautifully as their outrageously wealthy and flawed characters. Ryder considers Scorsese to be “the best director in the world” and their collaboration was a creative slam dunk. For her portrayal of the respectable and smitten May Welland, Ryder won the Golden Globe for Best Supporting Actress and was also nominated for an Academy Award. Empire magazine said, “Day-Lewis and Pfeiffer are on top form with Ryder giving the performance of her career.”
6 Girl, Interrupted
James Mangold’s 1999 psychological drama Girl, Interrupted stars Winona Ryder and Angelina Jolie and is based on writer Susanna Kaysen’s account of her 18-month stay in a psychiatric hospital following a suicide attempt between 1967 and 1968. Ryder acquired the rights to the novel herself and spent seven years trying to get the film made; she approached director James Mangold after seeing his film debut Heavy. Ryder plays Kaysen, who is diagnosed with borderline personality disorder and is admitted to the mental facility where she encounters sociopath Lisa Rowe, portrayed by the brilliant Angelina Jolie. While Girl, Interrupted was without-a-doubt Jolie’s introduction to Hollywood and an Oscar-winning role, it is widely regarded as one of Ryder’s best works and highlights the actress’ gift for bringing engaging stories and complicated characters to life. Famed critic Roger Ebert stated “Ryder shows again her skill at projecting mental states; one of her gifts is to let us know exactly what she’s thinking, without seeming too.”
5 Edward Scissorhands
Winona Ryder once again teamed up with the innovative and off-the-wall director Tim Burton for the 1990 fantasy romance film Edward Scissorhands. The unique story centers on an artificial man who was incompletely constructed with scissors for hands, and leads a solitary life until he is taken in by a kind suburban family. The titular character is portrayed by acting great Johnny Depp, who finds himself falling in love with the Boggs family’s kind and lovely daughter, Kim (Ryder). The epic fantasy flick includes additional roles played by Diane Wiest, Anthony Michael Hall, Kathy Baker, and horror icon Vincent Price in his final feature film performance. Ryder was the first cast member attached to the script, and famously starred alongside her then-boyfriend Depp for the picture. Edward Scissorhands was both a critical and financial success, earning numerous accolades and going on to become a beloved cult classic. Director Tim Burton cites the film as epitomizing his most personal work and regards it as his favorite creation.
4 Bram Stoker’s Dracula
The highly revered Francis Ford Coppola directed the 1992 gothic horror picture Bram Stoker’s Dracula, depicting the famed vampire’s journey to England on his crusade to seduce Jonathan Harker’s fiancé Mina Murray, whom he believes to be the reincarnation of his late wife. Winona Ryder brought the screenplay to Coppola, having revealed that, “what attracted [her] to the script is the fact that it’s a very emotional love story, which is not really what you think of when you think about Dracula. Mina, like many women in the late 1800s, has a lot of repressed sexuality.” Including the additional talents of Gary Oldman as Count Dracula himself, Keanu Reeves as Jonathan Harker, and Anthony Hopkins as Professor Abraham Van Helsing, Bram Stoker’s Dracula was a box office smash and went on to win three Academy Awards. The romantic horror picture is considered a game changer for the vampire genre by many critics, establishing a tone and style that redefined its cinematic approach.
The iconic 1988 Tim Burton fantasy comedy Beetlejuice revolves around a recently deceased couple who become ghosts who haunt their former home after the insufferable Deetz family moves in, and enlists the help of the devious ‘Betelgeuse’ to drive them out. The classic Burton film stars Alec Baldwin and Geena Davis as the newly-deceased husband and wife, with comedic genius Michael Keaton portraying the titular character and Winona Ryder as the macabre loving Lydia Deetz. Burton cast Ryder after seeing her in the 1986 romantic dramedy Lucas; the actress beat out other hopefuls including Alyssa Milano, Juliette Lewis, and Jennifer Connelly. Beetlejuice was a hit with both audiences and critics alike, winning the Academy Award for Best Makeup and three Saturn Awards. Keaton and Ryder’s performances were praised, as was Burton’s direction, with The Washington Post calling the picture “the perfect balance of bizarreness, comedy and horror.” The success of Beetlejuice spawned an animated television series, stage musical, and recurring discussions of a follow-up sequel.
Michael Lehmann’s 1989 teen black comedy Heathers takes place at Westerburg High, where a clique of four teenage girls viciously rule the school, three of whom are named Heather. Winona Ryder portrays outlier Veronica, a member of the popular clique who takes issue with their cruel behavior. Her world gets turned upside with the arrival of the mysterious new kid J.D. (Christian Slater), who captures her attention and harbors secret dark intentions. Ryder desperately wanted to play Veronica, having begged screenwriter Daniel Waters to give her a chance and even offering to work for free. Her agent was extremely opposed to her doing the film and warned her that it would ruin her career; nonetheless Ryder was cast and delivered an iconic performance that has since become one of her most beloved roles. On her portrayal, producer Denise Di Novi stated, “She was really sophisticated intellectually. She had the beauty of Veronica. She had the intelligence. She was just the perfect anti-Heather.” The black comedy premiered at the 1989 Sundance Film Festival and earned rave reviews, and is regarded as one of the greatest coming-of-age films and dark comedies of all time.
1 Little Women
Gillian Armstrong’s big screen adaptation of the classic Louisa May Alcott tale follows the famed March sisters as they experience growing pains, romance and family drama in mid-19th-century Massachusetts. With a compelling lineup of talented actresses including Winona Ryder, Claire Danes, Kirtsten Dunst, and Susan Sarandon, Little Women is a gorgeous retelling of the timeless story and is widely considered the best rendition of the Alcott staple. Ryder stars as the ambitious Jo March, who yearns for independence and harbors intense dreams of becoming a successful author. The actress received an Academy Award nomination for Best Actress for her moving portrayal, and nabbed the Kansas City Film Critics Circle Award for Best Actress. The New York Times wrote that Ryder’s “spirited presence gives the film an appealing linchpin, and she plays the self-proclaimed ‘man of the family’ with just the right staunchness.” Of the beloved adaptation, the moviestar revealed, “I’m very nostalgic about it, personally, because it’s one of my more, I think, more personal favorites.”
Great historical dramas show how the past, whether painful or bright, shapes each person and the world they live in.
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