Born in Minnesota, Winona Ryder made her film debut at the age of fifteen with David Seltzer’s Lucas. However, it was not until her first collaboration with Tim Burton two years later with the comedy fantasy Beetlejuice that Ryder was first properly recognised.
In Beetlejuice she played teen Goth Lydia with a wicked dress sense and a penchant for speaking to the dead. This kooky role introduced Ryder to audiences as the pale and beautiful isolated teen delicately trying to aid communication between this world and the next.
The controversial Heathers was released in the same year, an independent dark comedy film that satirised the epidemic of teenage suicide sweeping the fictional Westerburg High School. This cult classic progressed Ryder’s reputation for accepting the role of the outsider, the introspective teen trying to reach out to fellow misfits.
Her second, and hugely successful, collaboration with Tim Burton in 1990, firmly cemented this caring outsider reputation and jettisoned her into the hearts of the audience. As the young blond Kim in Edward Scissorhands, she stood in the minority alongside the loner Edward, played by the equally kooky and kindred misfit spirit Johnny Depp. The tender romance depicted in this Burton classic was no doubt aided by Ryder and Depp’s three year romance that began in 1990.
After a small yet significant role as the Tomboy Corky in Night on Earth, Ryder delved into a serious of different roles in novel adaptions; the dual interest of Dracula in Francis Ford Coppola’s Bram Stoker’s Dracula, the seemingly innocent May in Martin Scorsese’s The Age of Innocence, and the steadfast Jo in the classic Little Women.
In 1994 she returned to her familiar outsider role, as the fiercely intelligent Lelaina in Ben Stiller’s directorial debut, the romantic comedy drama Reality Bites. As a twenty something intelligent woman seeking an identity, this role paved the way for the best performance of her career, as Susanna Kaysen in Girl, Interrupted for which she was also the executive producer.
In 2000 she received a star on the Hollywood Walk of Fame before taking a hiatus from acting. She returned in 2006 in A Scanner Darkly an adaption of a Philip K. Dick sci-fi novel, who used to a family friend and then went on to star in the hugely successful Black Swan in 2010 and her final Burton collaboration, the animated Frankenweenie in 2012.
Despite her reputation for only playing kooky off the wall roles, Ryder’s career has currently lasted 24 years, in which she has played a variety of different characters. Perhaps she plays the beautiful and fiercely intelligent outsider the best as despite receiving a golden Globe award for Best Supporting Actress in The Age of Innocence, to many Ryder remains a blend of Burton’s supernatural Lydia and tender Kim.
12. Bram Stoker’s Dracula (1992) Dir. Francis Ford Coppola
In 1992 Ryder starred alongside Gary Oldman and Keanu Reeves (and his infamous British accent) in Bram Stoker’s Dracula. Ryder had brought the idea of the film to Francis Ford Coppola’s attention and she was cast in a dual role, Dracula’s modern day love interest Mina Harker and his past love Elisabeta.
Perhaps Ryder’s least captivating roles, she nonetheless plays both distinct characters well. As Mina, the fragile fiancé of Dracula’s solicitor, she portrays her corruptible innocence that teeters on the edge as she battles Dracula’s hypnotic affections. Her wide eyes, still face, and sweeping dresses establish Mina as the frightened lamb to Dracula’s domineering wolf. However as the film progresses and Mina falls deeper beneath Dracula’s spell Ryder plays Mina with a growing fiery sensuality and passion for the aged Vampire that is highly effective in depicting Dracula’s toxicating influence.
Although the film did well commercially, it did not do so well critically and Ryder’s performance in Bram Stoker’s Dracula is perhaps the weakest on the list.
11. Frankenweenie (2012) Dir. Tim Burton
Ryder had a small part in Tim Burton’s 2012 remake of his own film Frankenweenie. In 1984 Burton made the original live action version, in which the young boy Victor, distraught at the death of his doggy best friend, delves into Frankenstein’s science to re-animate him.
In the remade animated version, Ryder gave her voice to the young girl Elsa Van Helsing, the introspective next door neighbour and love interest of Victor. Elsa also has a dog, a kooky looking poodle called Persephone who falls in love with Victor’s raised from the dead dog, Sparky.
Ryder’s Elsa understands Victor’s heart ache over losing his beloved pet and her soulful appearance and soothing voice work together to project an empathy that is little seen amongst the other characters in Frankenweenie. As a bonus, Ryder also sang Elsa’s song and Elsa’a appearance is apparently based off of Ryder’s own Lydia of Beetlejuice.
10. The Age of Innocence (1993) Dir. Martin Scorsese
Ryder starred as May in Martin Scorsese’s tender take on Edith Wharton’s The Age of Innocence. Set in New York protagonist, Archer, played by Daniel Day Lewis, is a well to do young gentleman who is due to marry the seemingly innocent May when he begins to fall in love with Michelle Pfeiffer’s character. This new romance is doomed as were anyone to find out it would result in the exclusion for both characters from New York society.
Ryder plays Archer’s sensible choice, the seemingly naïve May, whose kind gestures and wide eyes liken her to young doe. However, Ryder’s subtle acting slowly divulges that May is not as innocent as she appears. Her deliberate overt youthfulness is revealed to conceal a sharp mind deliberately trapping Archer in his traditional values. Her long mooning glances that Ryder uses to present complete trust in Archer also act to bind him to May, forcing him to stick to his privileged societal values at the expense of his love for Pfieffer.
Ryder’s handle of the duplicitous May shone through in her complex and subtle acting and rightly earned her a Golden Globe Award for Best Supporting Actress.
9. Little Women (1994) Dir. Gillian Armstrong
In the third book adaption on this list, Ryder played Jo, the aspiring author and one of a family of four sisters in Little Women. Based on the classical novel written by Lousia May Alcott, the film features a star-studded cast; Claire Danes, Kirsten Dunst, Christian Bale, and Susan Sarandon taking leading roles.
Set in Massachusetts around the American Civil War, the March family struggle to navigate their daily lives involving growing up and missing their father who is away participating in the fight as a soldier. The plot covers a period of over four years in which the sisters grow up, get married, refuse proposals, or in the case of Beth, become fatally ill after a bout of Scarlet Fever.
Ryder plays the strong-willed and often stormy Jo who frequently argues with the wealthy boy next door Laurie (played by the young and talented Christian Bale). In a memorable scene Jo and Laurie are enjoying one another’s company on a sunny day when Laurie bemoaning the life that has already been set out for him, asks for Jo’s hand in marriage.
Jo’s prompt dismissal does not deter him, and Ryder’s playful yet tortured acting throughout his speech reveals Jo to be a complex character who ultimately remains single until the end in order to follow her dreams to write whilst regretting the pain she has caused Laurie.
8. Night On Earth (1991) Dir. Jim Jarmusch
Ryder had a small but significant role in Night on Earth in 1991. At the age of 20, Ryder played the tomboy Corky, a cursing, tough-as-nails, chain-smoking taxi cab driver who dreams of being a mechanic. One night in L.A., Corky picks up a casting agent (Gena Rowlands) and drives her to her destination in Beverly Hills.
In the opening 25 minutes of the film Ryder fully fleshes out the character of Corky; she smokes too much, comes from a family of brothers, and in her baggy shirts and backwards cap, does not care about impressing anybody. Compared to the stressed, uptight, and well-dressed casting agent, gum-chewing Corky seems youthful and refreshingly straight forward.
It is Ryder’s affectations she uses to play Corky which make her stand out, her well timed changing facial expressions, and her subtle eye glances shape Corky to be a street-wise girl with no aspirations to be considered as anything other than a mechanic. Her slouching posture and easy smile establish her as easy-going yet no nonsense taking.
Corky dismisses the casting agent’s opportunity of a starring role in a film and Ryder’s portrayal leaves no doubt the steadfast Corky will succeed in her mechanic dreams.
7. Reality Bites (1994) Dir. Ben Stiller
In 1994, Ryder played the lead role in Reality Bites, an off-beat romantic comedy and directorial debut of Ben Stiller (who also starred as one of Ryder’s love interests). Although technically it was not a huge commercial success, the film was critically well received.
Ryder played Lelaina, a recently graduated Valedictorian who lives with her fellow graduates who are all now struggling to navigate the corporal world whilst holding on to the dreams and ideals they fostered throughout university. Lelaina aspires to be a documentary filmmaker and films her friends’ daily lives, hoping to capture some visual truth in the way that they live.
After being fired from her job for punishing the brutish television presenter she works for, Ryder portrays Lelaina beginning to question her creative identity and longing for a sense of direction. Lelaina is also caught between two guys; the emotionally mature and full time working Michael (Stiller) and the super cool, fired from twelve jobs Troy (Ethan Hawke). After Michael’s company edits Lelaina’s documentary to the point it no longer resembles her artistic vision, she leaves Michael in frustration.
Ryder’s steadfast Lelaina remains deeply concerned with the formation of identity, and she is successful in depicting Lelaina’s progression throughout the ups and downs of navigating employability, relationships, and parents.