Winona Ryder

Winona Ryder

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Birth name: Winona Laura Horowitz
Date of birth: 29 October 1971
Place of birth:  Winona, Minnesota, USA 
Nickname:  Noni
Height: 5′ 4″ (1.63 m)

Famous Quote: “I read biographies of the greats, and they were so messed up that I thought I’d better mess myself up. But I couldn’t. I’m too small.I didn’t have this tremendous sense of guilt because I hadn’t hurt anyone. Had I physically harmed someone or caused harm to a human being, I think it would have been an entirely different experience.”

Contact Address and Autograph: Addresses and fan mail information

Winona Ryder
William Morris Agency
One William Morris Place
Beverly Hills, CA 90212, USA 

Biography: Winona Laura Horowitz (born October 29, 1971), better known under her professional name Winona Ryder, is a two-time Academy Award-nominated and Golden Globe-winning American actress. Although Ryder made her screen debut in Lucas (1986), her first significant role came in 1988 with Beetlejuice as Lydia, a Goth teenager, in a performance that gained her critical and commercial recognition. After making various appearances in film and television, Ryder continued her career with the cult film Heathers (1989) in a prominent and critically acclaimed performance. Her subsequent roles have not only won her critical praise but numerous film awards. In 2000, Ryder received a star on the Walk of Fame in Hollywood, California.

Ryder is known for her relationship with actor Johnny Depp throughout the early 1990s. She also received noteworthy media attention for her participation in the investigation of the kidnapping and murder of Polly Klaas in 1993, who was from Ryder’s hometown. Ryder also received worldwide attention after her arrest on December 12, 2001 for shoplifting from a Saks Fifth Avenue store in Beverly Hills, California.

Born Winona Laura Horowitz in Olmsted County, Minnesota, she was named after the nearby city of Winona. She was given her middle name, Laura, because of her parents’ friendship with Aldous Huxley’s wife, Laura Huxley. Her mother, Cynthia Palmer (née Istas), is an author, as well as a video producer and editor. Her father, Michael Horowitz, is an author, editor, publisher and antiquarian bookseller. 

Ryder’s mother is a Buddhist and her father is an atheist. Regarding her ancestry, Ryder has described herself as “Jewish”, her paternal grandparents were Jewish immigrants from Russia, and relatives of hers died in the Holocaust. Ryder has one sibling, a younger brother, Yuri, an older half-brother, Jubal, and an older half-sister, Sunyata. Ryder’s family friends included her godfather, LSD guru Timothy Leary, and beat poets Allen Ginsberg and Lawrence Ferlinghetti.

In 1978, when Ryder was seven years old, she and her family relocated to Rainbow, a commune near Elk, California, where they lived with seven other families on a 300-acre (1.2 km²) plot of land. As the remote property had no electricity or television sets, Ryder began to devote her time to reading and became an avid fan of J.D. Salinger’s Catcher in the Rye. She developed an interest in acting after her mother showed her a few movies on a screen in the family barn. At age 10, Ryder and her family moved on again, this time to Petaluma, California. During her first week at the Kenilworth Middle School, she was bullied by a group of her peers who mistook her for an effeminate, scrawny boy.

As a result, she ended up being homeschooled that year. In 1983, when Ryder was 12, she enrolled at the American Conservatory Theater in nearby San Francisco, where she took her first acting lessons. Ryder graduated from Petaluma High School with a 4.0 GPA in 1989. She has also revealed that she suffers from aquaphobia due to the trauma caused by an incident in which she nearly drowned at age 12. This caused problems when she had to act in some of the underwater scenes in Alien: Resurrection (1997) and the scenes had to be reshot numerous times.

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 coupe when cast in the role of Spock’s mother in J.J. Abrams reimagined film franchise, “Star Trek” (2008).

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.

In 1985, Ryder sent a videotaped audition, where she recited a monologue from the novel Franny and Zooey, to appear in the film Desert Bloom. She was rejected and the part went to Annabeth Gish. Despite her rejection, David Seltzer, a writer and director, soon noticed her talent and cast her in his 1986 film Lucas. When asked how she wanted her name to appear in the credits, she suggested “Ryder” as her surname as a Mitch Ryder album which belonged to her father was playing in the background. 

Her next movie was Square Dance (1987), where her teenage character creates a bridge between two different worlds — a traditional farm in the middle of nowhere and a large city. Ryder won acclaim for her role, and The Los Angeles Times called her performance in Square Dance “a remarkable debut”. Both films, however, failed to gain Ryder any notice, and were only marginally successful commercially. Director Tim Burton decided to cast Ryder in his film Beetlejuice (1988), after being impressed with her performance in Lucas. In the film, she plays gothic teenager Lydia Deetz. Lydia’s family moves to a haunted house populated by ghosts played by Geena Davis, Alec Baldwin, and Michael Keaton. Lydia quickly finds herself the only human with a strong empathy toward the ghosts and their situation. The film was a success at the box office, and Ryder’s performance and the overall film received mostly positive reviews from critics.

Ryder landed the role of Veronica Sawyer in the 1989 independent film Heathers. The film, a satirical take on teenage life, revolves around Veronica, who is ultimately forced to choose between the will of society and her own heart after her boyfriend (Christian Slater) begins killing popular high school students. Ryder’s agent initially begged her to turn the role down, saying the film would “ruin her career”. Reaction to the film was mostly lukewarm, but Ryder’s performance was critically embraced, with The Washington Post stating Ryder is “Hollywood’s most impressive inge’nue [sic] … Ryder … makes us love her teen-age murderess, a bright, funny girl with a little Bonnie Parker in her. She is the most likable, best-drawn young adult protagonist since the sexual innocent of Gregory’s Girl.” The film was a box office flop, yet achieved status as a predominant cult film. 

Later that year, she starred in Great Balls of Fire!, playing the 13-year-old bride (and cousin) of Jerry Lee Lewis. The film was a box office failure and received largley divided reviews from critics. In April 1989, she played the title role in the music video for Mojo Nixon’s “Debbie Gibson Is Pregnant with My Two-Headed Love Child”. In 1990, Ryder was selected for four film roles. In Edward Scissorhands (1990), she played the leading female role alongside her then-boyfriend Johnny Depp. The film reunited Tim Burton and Ryder, who had previously worked together on Beetlejuice in 1988. Edward Scissorhands was a significant box office success, grossing US$56 million at the United States box office and received much critical devotion. 

Later that year, she withdrew from a role in Francis Ford Coppola’s The Godfather Part III, after traveling to Rome, Italy, for filming due to over-exhaustion. Eventually, Coppola’s daughter Sofia Coppola was was cast in the role. Ryder’s third role was in the family comedy-drama Mermaids (1990), which co-starred Cher and Christina Ricci. Mermaids was a moderate box office success and was embraced critically. Ryder’s performance was also acclaimed; critic Roger Ebert of the Chicago Sun-Times wrote: “Winona Ryder, in another of her alienated outsider roles, generates real charisma.” For her performance, Ryder received a Golden Globe nomination for Best Actress in a Supporting Role. Ryder then performed alongside Cher and Christina Ricci in the video for “The Shoop Shoop Song”, the theme from Mermaids. Following Mermaids she starred in the lead role in box office flop Welcome Home, Roxy Carmichael (1991).

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.

In 1991, Ryder played a young taxi driver who dreams of becoming a mechanic in Jim Jarmusch’s Night on Earth. The film was only given a limited release at the box office, but received critical praise. Ryder then starred in the dual roles of Count Dracula’s reincarnated love interest Mina Murray and Dracula’s past lover Princess Elisabeta, in Bram Stoker’s Dracula (1992), a project she brought to director Francis Ford Coppola’s attention. In 1993, she starred in the melodrama The House of the Spirits, based on Isabel Allende’s novel. 

Ryder played the love interest of Antonio Banderas’ character. Principal filming was done in Denmark and Portugal. The film was poorly reviewed and a box office flop, grossing just $6 million on its $40 million budget.] Ryder also starred in The Age of Innocence with Michelle Pfeiffer and Daniel Day-Lewis, a film based on a novel by Edith Wharton and helmed by director Martin Scorsese, whom Ryder considers “the best director in the world”. Her role in this movie won her a Golden Globe Award for Best Supporting Actress as well as an Academy Award nomination in the same category.

Ryder’s next role was in the Generation X drama Reality Bites (1994), playing a young woman searching for direction in her life. Her performance received acclaim and the studio hoped the film would gross a substantial amount of money, yet it flopped. Bruce Feldman, Universal Pictures’ Vice-President of Marketing said: “The media labeled it as a Generation X picture, while we thought it was a comedy with broad appeal.” The studio placed TV ads during programs chosen for their appeal to 12–34-year-olds and in interviews Stiller was careful not to mention the phrase “Generation X”. 

In 1994, Ryder was handpicked to play the lead role of Josephine March in Little Women, an adaptation of Louisa May Allcott’s novel. The film received widespread praise; critic Janet Maslin of The New York Times wrote that the film was the greatest adaptation of the novel, and also remarked on Ryder’s performance: “Ms. Ryder, whose banner year also includes a fine comic performance in ‘Reality Bites,’ plays Jo with spark and confidence. Her spirited presence gives the film an appealing linchpin, and she plays the self-proclaimed ‘man of the family’ with just the right staunchness.” She also received an Best Actress Oscar nomination the following year. 

She also made a guest appearance in The Simpsons episode “Lisa’s Rival” as Allison Taylor, whose intelligence and over-achieving personality makes her a rival of Lisa’s. Her next starring role was in How to Make an American Quilt (1995), an adaptation of the novel of the same name by Whitney Otto, co-starring Anne Bancroft. Ryder plays a college graduate who spends her summer hiatus at her grandmother’s property to ponder on her boyfriend’s recent marriage proposal. The film was not a commercial success, nor was it popular with critics.

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.

Ryder made several film appearances in 1996, the first in Boys. The film failed to become a box office success and attracted mostly negative critical reaction. Roger Ebert of the Chicago Sun-Times stated that “Boys is a low-rent, dumbed-down version of Before Sunrise, with a rent-a-plot substituting for clever dialogue.” Her next role was in Looking for Richard, Al Pacino’s documentary on a production of Shakespeare’s Richard III, which grossed only $1 million at the box office, but drew moderate critical acclaim. 

She also starred as the lead in The Crucible, alongside Daniel Day-Lewis and Joan Allen. The film, an adaptation of Arthur Miller’s play, centered on the Salem witch trials. The film was expected to be a success, considering its budget, but became a large failure. Despite this, it received acclaim critically, and Ryder’s performance was lauded, with Peter Travers of Rolling Stone saying, “Ryder offers a transfixing portrait of warped innocence.” In December 1996, Ryder accepted a role as a humanoid robot in Alien: Resurrection (1997), alongside Sigourney Weaver, who had appeared in the entire Alien trilogy. Ryder’s brother, Suri, was a major fan of the film series, and when asked, she took the role. The film became one of the least successful entries in the Alien film series, but was considered a success as it grossed $161 million worldwide. Weaver’s and Ryder’s performances drew mostly positive reviews, and Ryder won a Blockbuster Entertainment Award for Best Actress. Ryder then starred in Woody Allen’s Celebrity (1998), after Drew Barrymore turned down Ryder’s role, in an ensemble cast. The film satirizes the lives of several celebrities.

In 1999, she performed in and served as an executive producer for Girl, Interrupted, based on the 1993 autobiography of Susanna Kaysen. The film had been in project and post-production since late 1996, but it took time to surface. Ryder was deeply attached to the film, considering it her “child of the heart”. Ryder starred as Kaysen, who has borderline personality disorder and was admitted to a mental hospital for recovery. Ryder starred alongside Whoopi Goldberg and Angelina Jolie. While Ryder was expected to make her comeback with her leading role, the film instead became the “welcome-to-Hollywood coronation” for Jolie, who won an Academy Award for Best Supporting Actress for her performance. In Jolie’s acceptance speech, she thanked Ryder.

Also in 1999, Ryder was parodied in South Park: Bigger, Longer and Uncut. The following year, she starred in the romantic comedy Autumn in New York, alongside Richard Gere. The film revolves around a relationship between an older man (Gere) and a younger woman (Ryder). Autumn in New York received mixed reviews, but was a commercial success, grossing $90 million at the worldwide box office. Ryder then played a nun of a secret society loosely connected to the Roman Catholic Church and determined to prevent Armageddon in Lost Souls (2000), which was a commercial failure. Thus, Ryder refused to do commercial promotion for the film. Later in 2000, she was one of several celebrities who made a small cameo appearance in Zoolander. On October 6, 2000, Ryder received her own star on the Hollywood Walk of Fame, located directly in front of the Johnny Grant building next to the Hollywood Roosevelt Hotel on Hollywood Boulevard. She was the 2,165th recipient of this honor.

Ryder had a moderate hiatus after her shoplifting incident in 2001 (see below). The book Conversations with Woody Allen reports that in 2003 film director Woody Allen wanted to cast Robert Downey Jr. and Ryder in his film Melinda and Melinda, but was unable to do so because “I couldn’t get insurance on them … We couldn’t get bonded. The completion bonding companies would not bond the picture unless we could insure them. [...] We were heartbroken because I had worked with Winona before [on Celebrity] and thought she was perfect for this and wanted to work with her again.”

In 2002, Ryder appeared in two films. The first was a romantic comedy titled Mr. Deeds with Adam Sandler. This was her most commercially successful movie to date, earning over $126 million in the United States alone. She played a cynical reporter for an unscrupulous television program. The second film was the science fiction drama S1m0ne in which she portrayed a glamorous star who is replaced by a computer simulated actress due to the clandestine machinations of a director, portrayed by her Looking For Richard costar Al Pacino.

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.

In 2006, after an extensive hiatus, Ryder appeared in Richard Linklater’s A Scanner Darkly, a science fiction film based on Philip K. Dick’s critically acclaimed 1977 novel. Ryder starred alongside Keanu Reeves, Robert Downey Jr, and Woody Harrelson. Live action scenes were transformed with rotoscope software and the film was entirely animated. A Scanner Darkly was screened at the 2006 Cannes Film Festival and the 2006 Seattle International Film Festival. Critics disagreed over the film’s merits; Carina Chocano of the Los Angeles Times found the film “engrossing” and wrote that “the brilliance of [the film] is how it suggests, without bombast or fanfare, the ways in which the real world has come to resemble the dark world of comic books.” Similarly, Matthew Turner of ViewLondon, believing the film to be “engaging” and “beautifully animated”, also praised the film for its “superb performances” and original, thought-provoking screenplay.Ryder also recently appeared in the comedy The Darwin Awards, starring alongside Joseph Fiennes. The film premiered at the Sundance Film Festival on January 25, 2006.

Ryder also confirmed in an interview with Entertainment Weekly she is reuniting with Heathers screenwriter Daniel Waters for the surreal black comedy Sex and Death 101 (2007). The story follows the sexual odysseys of successful businessman Roderick Blank, played by Simon Baker, who receives a mysterious e-mail on the eve of his wedding, listing all of his past and future sex partners. “We will be doing a sequel to Heathers next.” Ryder stated. “There’s Heathers in the real world! We have to keep going!”. In a more recent interview Ryder was quoted as saying on the speculation of a Heathers sequel: “I don’t know how much of the movie is official; it’s a ways away. But it takes place in Washington and Christian Slater agreed to come back and make an Obi-Wan-type appearance. It’s very funny.”

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” (2008) received the most advance press, signaling Ryder’s unequivocal return to Hollywood, with all forgiven. 

Ryder also appeared in David Wain’s comedy The Ten, alongside Jessica Alba, Paul Rudd, Justin Theroux, Famke Janssen, Oliver Platt, and Adam Brody. The film centers around ten stories, each of them inspired by one of the Ten Commandments. The film debuted at the Sundance Film Festival 2007 on January 10, 2007,with a theatrical release on August 3, 2007. Ryder will play the female lead opposite Wes Bentley and Ray Romano in Geoffrey Haley’s offbeat romantic drama The Last Word. She has also signed up to appear as a newscaster in the upcoming movie version of The Informers, will join Robin Wright and Julianne Moore in Rebecca Miller’s The Private Lives of Pippa Lee, which is scheduled to start filming in April 2008 in Connecticut, and will appear in Paramount Pictures’ and director JJ Abrams’s Star Trek (2009), as Spock’s mother Amanda Grayson, a role originally played by Jane Wyatt.

Ryder has had many high-profile relationships with actors. She was engaged to actor Johnny Depp for three years beginning in July 1990.During their relationship, Depp had a tattoo placed on his arm reading “Winona Forever”, which he had altered to “Wino Forever” after their separation. Ryder later had serious relationships with Soul Asylum’s Dave Pirner, the drummer and singer Dave Grohl and actor Matt Damon. Ryder also told W Magazine in a June 2002 issue that she is close friends with comedian and actor Jimmy Fallon. She was also close friends with actress Gwyneth Paltrow, until they reportedly “grew apart” in the late 1990s. She is currently dating Rilo Kiley guitarist Blake Sennett.

In 1993, Ryder became involved in the Polly Klaas kidnapping case. Klaas lived in Petaluma, the same town where Ryder grew up. Ryder offered a $200,000 reward for the 12-year-old kidnap victim’s safe return. After the girl’s death, Ryder starred in the 1994 film adaptation of Little Women by Louisa May Alcott and dedicated it to her memory. Little Women was one of Polly’s favorite novels.

During a sentencing hearing related to the 2001 shoplifting incident (see below), Ryder’s attorney, Mark Geragos, referred to her work with the Polly Klaas Foundation and other charitable causes. In response, Deputy District Attorney Ann Rundle said: “What’s offensive to me is to trot out the body of a dead child.” Ryder was visibly upset at the accusation and Rundle was admonished by the judge. Outside the courthouse, Polly’s father Mark Klaas defended Ryder and expressed outrage at the prosecutor’s comments

On December 12, 2001, Ryder was arrested on shoplifting charges in Beverly Hills, California; she stood accused of stealing $5,500 worth of designer clothes and accessories at a Saks Fifth Avenue department store. Los Angeles District Attorney Stephen Cooley produced a team of eight prosecutors. Cooley filed four felony charges against her in what was described by British newspaper The Guardian as a “show-trial”. Ryder hired noted celebrity defense attorney Mark Geragos. Negotiations for a plea-bargain failed at the end of summer 2002. 

As noted by Joel Mowbray from the National Review, the prosecution was not ready to offer the actress what was given to 5,000 other defendants in similar cases, an open door to a no-contest plea on misdemeanor charges. Ryder agreed under signature to pay two Civil Demands, as permitted under California’s Statute for Civil Recovery for Shoplifting, from Saks Fifth Avenue that would completely reimburse Saks Fifth Avenue for the stolen and surrendered merchandise while detained in the Security Offices of the Saks Fifth Avenue store, and before she was mirandized and arrested by the Los Angeles Commissioned Police.

During the trial, she was also accused of using drugs without valid prescriptions. Ryder was convicted of grand theft and vandalism, but was acquitted on the third felony charge, burglary. In December 2002, she was sentenced to three years’ probation, 480 hours of community service, $3,700 in fines, and $6,355 in restitution to the Saks Fifth Avenue store – and was ordered to attend psychological and drug counseling by the judge. After reviewing Ryder’s probation report, Superior Court Judge Elden Fox noted that Ryder served 480 hours of community service and on June 18, 2004, the felonies were reduced to misdemeanors. Ryder remained on probation until December 2005.