An icon of 1990s film, actress Winona Ryder first earned a loyal following for giving unusual depth and inner life to teen characters in films like “Heathers” (1989) and “Edward Scissorhands” (1990). Her enormous, expressive brown eyes and a radiance that reminded early champion Tim Burton of the "timeless old movie stars" went on to become a favorite element in period dramas like “Bram Stoker’s Dracula” (1992), “The Age of Innocence” (1994) and “The Crucible” (1996), as well as the perfect angst-ridden teen in films like “Reality Bites.” Personally, the nineties “It” girl’s love life enthralled fans and the press alike, as each move made with famous boyfriends Johnny Depp and Matt Damon was chronicled religiously. Following Ryder’s executive producer debut with “Girl, Interrupted” (1999), her career stammered with several theatrical flops and a high-profile shoplifting incident that painted a portrait of an actress who had not only lost her career footing but her sense of right and wrong. She separated from Hollywood for several years, but the public was forgiving, with Ryder returning with a string of independent films in 2007 and scoring a major coup when cast in the role of Spock’s mother in J.J. Abrams reimagined film franchise, “Star Trek” (2009).
Winona Laura Horowitz was born near Winona, MN, on Oct. 29, 1971. The child of counterculture writers Michael Horowitz and Cynthia Palmer Horowitz, the young girl grew up surrounded by some of the brightest literary lights of the era, with Timothy Leary for a godfather and regular visits with poets Allen Ginsberg and Lawrence Ferlinghetti. The family relocated to San Francisco soon after Ryder was born and moved onto a commune in Northern California’s Mendocino County when she was 10. There she cohabitated with seven other families on a farm without electricity or running water, though her mother used to screen movies in a nearby barn. It was there that Ryder was first inspired to act by watching the films of John Cassavetes — not your usual entertainment for 10 year olds. Nudity, free love, and drag queens were as much a part of her every day life as trips to the outhouse, and when the family moved to a more traditional living situation in the San Francisco suburb of Petaluma, an outcast Ryder with her strange clothes and hair and no-rules parents found herself longing to fit in.
An unwelcome arrival at Kenilworth Middle School was followed by the decision to home-school Ryder, an avid reader and naturally curious 12-year-old who was wise beyond her years. To add spice to her home study program, her parents enrolled her in acting classes at San Francisco's American Conservatory Theatre. The following year, Ryder performed a favorite monologue from J.D. Salinger’s “Franny & Zooey” when she was spotted by a talent scout and screen tested for a role in "Desert Bloom" (1986). The film role went to Annabeth Gish, but the audition tape found its way to director David Seltzer, who cast her as best friend of the title character "Lucas” (1986) in the now-classic teen film. “Lucas” was literally the debut of Winona Ryder, who adopted her professional surname from 1960s rock group Mitch Ryder and Detroit Wheels.
With her flexible home-schooling schedule enabling her to pursue further acting work, Ryder followed up with a role as a Texas teenager torn between her grandfather (Jason Robards) and her mother (Jane Alexander) in "Square Dance" (1987), walking away with the best reviews in the film. Her personal experience as a suburban reject was a handy reference point in Tim Burton’s, "Beetlejuice" (1988), a breakout part that won her significant audience and critical recognition. Ryder nailed her supporting role as a morose, black-clad teen thoroughly alienated from her yuppie parents; nearly stealing the film from co-stars Michael Keaton, Alec Baldwin and Geena Davis with her perfectly deadpan vocal delivery. Further solidifying her reputation as a queen of teen inner turmoil, she defied her agent and took a leading role in the dark comedy "Heathers” (1989), deftly negotiating complex terrain as her character evolved from passive hanger-on to murderer with a conscience, all the while retaining the audience's affection.
Ryder banked on her doe-eyed innocence and pulled off a heroic feat of naiveté in "Great Balls of Fire!" (1989), playing the 13-year-old bride of famed piano man Jerry Lee Lewis (Dennis Quaid). The following year, she graduated from Petaluma High School with a 4.0 grade point average and appeared as the offbeat but intelligent Dinky in "Welcome Home, Roxy Carmichael" (1990). Ryder reteamed with Burton (and shared the screen with future boyfriend Johnny Depp) to deliver a naturalistic portrait of a young woman at first repulsed then later drawn to the freakish but gentle "Edward Scissorhands" (1990). Although the director did not depict her as thoroughly disaffected, he certainly took ample shots himself at the cookie-cutter conformity of suburban existence. Ryder again called on her own background to inform her portrayal of Cher's eldest daughter in "Mermaids" (1990), her character dreaming of structured nunhood as an escape from the unconventional lifestyle of her mother. Ryder received the film's best notices and picked up her first acting award from the National Board of Review.
The success of “Edward Scissorhands” put breakout stars Depp and Ryder in the headlines, where the tragically hip twosome evolved into the poster couple of the early 90s. With their rumpled thrift store clothes and offbeat film choices, Ryder and Depp embodied the emerging spirit and values of alternative music and Generation X. The pair was engaged in 1990, with Depp famously receiving the tattoo “Winona Forever” on his forearm. Though still a young woman, the 19-year-old actress began to shift her career away from teen angst roles in the search for substantial young adults to embody. A mysterious illness – some called it a “nervous breakdown” – forced her out of the pivotal role of Mary Corleone in Francis Ford Coppola's "The Godfather, Part III" (1990), but upon her recovery, Jim Jarmusch tapped her to play a tomboyish cab driver in “Night on Earth” (1991). Ryder was sadly unconvincing in the feminist renegade role created for her, but fared better in another attempt to go against type in Coppola’s "Bram Stoker's Dracula" (1992). Her pale, sylph-like beauty was perfect for the period piece, and Ryder provided the film's emotional core without being overshadowed by its phantasmagoric special effects, lavish production design and showier co-stars – most of whom were annihilated by critics for their camping overacting – i.e. Keanu Reeves and Gary Oldman.
Martin Scorsese recruited Ryder for his remake of "The Age of Innocence" (1993), in which she built on the air of sophistication developed opposite Anthony Hopkins in "Dracula," swooshing around in hooped dresses and earning an Oscar nomination for portraying the demure yet strong-willed May Welland, whose fiancé (Daniel Day-Lewis) has fallen in love with her cousin (Michelle Pfeiffer). Later in the year, Ryder lent her star power to a sad hometown cause when 12-year-old Polly Klaas was kidnapped from her home in Petaluma, CA. Ryder helped publicize a search for the young girl and offered a $20,000 reward, but sadly Klaas was found dead several months later. In memoriam, Ryder worked hard to bring an adaptation of Klaas’ favorite book, Louisa May Alcott’s "Little Women" (1994), to the screen. As ringleader of the spirited "Little Women," Ryder delivered a strong performance in what was arguably one of the best screen renditions of the novel, garnering her a second Oscar nomination.
Ben Stiller's directorial debut "Reality Bites" (1994) offered Ryder the chance to lose the period garb and don jeans, playing an ambitious college grad struggling to find a medium ground between joining the corporate ranks and succumbing to cynical slackery—choices embodied by suitors Ben Stiller and Ethan Hawke. The timeless theme suffered a bit from heavy-handed hipness, but Ryder acquitted herself well and earned critical praise for her work. Offscreen, the end of Ryder and Depp’s engagement and her new relationship with Soul Asylum guitar player Dave Pirner reinforced her position as the alternative “It” girl of the ‘90s. Ryder continued to impress, essaying a graduate student who learns about life and love in "How to Make an American Quilt" (1995) and was an excellent casting choice to voice an audio version of “The Diary of Anne Frank” for which she earned a Grammy nomination for Spoken Word Album. She tried her hand at Shakespeare, playing Lady Anne in Al Pacino's award-winning documentary "Looking for Richard" (1996), before she was again cast opposite Day-Lewis in an adaptation of Arthur Miller's stage play "The Crucible" (1996), proving her mettle as a scorned woman seeking revenge by fabricating tales of witchcraft.
Broadening her efforts to be accepted in adult roles, Ryder teamed with Sigourney Weaver to battle the monsters of the "Alien" franchise in "Alien Resurrection" (1997), but she was admittedly out of her element. Following a small but luminous role in Woody Allen's "Celebrity" (1998), Ryder saw her first executive produced feature come to fruition with "Girl, Interrupted" (1999), an adaptation based on Susanna Kaysen's memoir of her experience at a mental hospital in the 1960s. Ryder rose above the script's limitations to credibly render the rich, spoiled and confused 17-year-old lead, though Angelina Jolie trumped her as the irrepressible sociopath more responsible for Susanna's rehabilitation than the doctors. Jolie would, in fact, earn the Oscar for her role, while Ryder was not even nominated. The following year saw her star in the exorcism thriller "Lost Souls" and the woefully bad "Autumn in New York," in which she played a dying woman romanced by a playboy (Richard Gere). Both films garnered few critical thumbs-up and even fewer ticket sales.
By the end of 2001, it was beginning to look like Ryder was losing her sense of identity and her core audience. The girl who had made a name as a generation X icon and the cunning innocent of lavish period pieces was now hitting age 30 and in search of a fitting niche for her undeniable charm and intelligence. The treading actress seemed close to sinking in December of 2001, however, when she was arrested for shoplifting at the Beverly Hills department store Saks Fifth Avenue after she had been captured on videotape and observed by security guards lifting nearly $6,000 worth of the swanky store's high-end merchandise, cutting off sensor tags and secreting the items in shopping bags. Following a high-profile media circus that unflatteringly portrayed the actress as a has-been and drug addict – she was taking prescription painkillers for a recently broken arm, but had a full arsenal of meds in her purse at the time of the arrest – Ryder's trial commenced on Oct. 24, 2002, and in a strange quirk of fate, one of the jurors was producer Peter Guber, a former studio head who gave the greenlight to three films starring Ryder ("Dracula," "The Age of Innocence" and "Little Women") while he was the co-head of Sony Studios in the early 1990s. During th trial, the actress' attorney argued that Ryder had bought several items prior to her arrest and instructed a salesperson to keep her account open (no evidence that she had such an arrangement was presented); further, he argued that Saks employees had targeted the actress in hopes of selling the story of her arrest. Prosecutors successfully refuted the conspiracy claims and on Nov. 6, 2002, Ryder was convicted of two of the three charges against her: theft and vandalism. Ryder’s felony charges were eventually reduced to misdemeanors and she was ordered to pay fines and restitution and perform community service. She wisely refrained from making any public statements until years later, though she did pose for the cover of W magazine wearing a "Free Winona" t-shirt.
Ryder decided to lay low following the ordeal, moving to San Francisco and turning down film offers. The film she had been working on when she broke her arm, the Adam Sandler comedy "Mr. Deeds" (2002), was released and marked her biggest box office draw to date, though the co-star’s likeness was oddly absent from the film’s marketing campaign. In general, Ryder was well-received for her first foray into madcap comedy. In 2003, she narrated a documentary about child slavery called “The Day My God Died” (2003) but did not return to the screen in full force until she starred, in digitized form, in Richard Linklater’s “A Scanner Darkly” (2006). The Philip K. Dick adaptation received limited independent release, but met with generally favorable reviews for its thought provoking portrayal of a dystopian future and for the visual impact of its rotoscoping animation technique.
Ryder inched her way back into the film world with several features in 2007, including the commandment-inspired “The Ten,” in which Ryder helmed a segment devoted to “Thou shalt not steal.” She reunited with “Heathers” writer-director Daniel Waters to star in “Sex and Death 101” (2007), playing a femme fatale who adds to the doubts of a commitment-fearing fiancé. In 2008, Ryder was slated to play a recent widow and love interest of the man who ghost-authored her husband’s suicide letter in “The Last Word,” an offbeat drama co-starring Ray Romano and Wes Bentley. She would also appear in Bret Easton Ellis’ “The Informers,” but her casting as Spock’s human mother in J.J. Abrams feature film relaunch of “Star Trek” (2009) received the most advance press, signaling Ryder’s unequivocal return to Hollywood, with all forgiven.