of Susanna Kaysen. Ryder was deeply attached to the film, considering it her "child of the heart"; she played the Kaysen character, who had a borderline personality disorder and was calm and reserved in contrast to the supporting role enacted by Angelina Jolie of a sociopath full of sexual energy and prone to dramatic episodes. It was Jolie's performance that captured the attention of the public and the Academy.
She went on to portray the fragile, beautiful, young, talented and doomed love interest of Richard Gere's character in the 2000 romance Autumn in New York.
In the same year she played a sister (a nun) of a secret society loosely connected to Roman Catholic Church determined to prevent Armageddon - Lost Souls, which did not do well at the box office. The character struggles between the world (including the Church) laughing at the supernatural, her own beliefs based on personal experience and uncertainty between seemingly obvious empirical evidence and her doubts in her own sanity, and a questionable ability to reason or even perceive correctly.
2001-2005
In 2002, Ryder appeared in two films, one a romantic comedy titled Mr. Deeds (alongside Adam Sandler), where she played a cynical reporter for an unscrupulous television program, and the other an episodic role in S1m0ne, in which she portrayed a glamorous star who is replaced by a computer simulated actress due to the clandestine machinations of a director (played by Al Pacino).
2006-beyond
Winona Ryder as Donna in A Scanner Darkly (2006)
In 2006, after a long dry spell, Ryder appeared in Richard Linklater's A Scanner Darkly, a futuristic movie based on Philip K. Dick's critically acclaimed novel. Ryder portrayed Donna Hawthorne also starring are Keanu Reeves, Robert Downey Jr and Woody Harrelson. Live action scenes were transformed with rotoscope software and the film was entirely animated.
Ryder will be busy in 2007 with three films due to come out. She will first star in the comedy The Darwin Awards, due for release February 2007, with Joseph Fiennes about a forensic detective (Fiennes) and an insurance claims investigator (Ryder) trekking to investigate a potential Darwin Award winner.
Second, Ryder is reuniting with Daniel Waters, who wrote Heathers, for the surreal dark comedy Sex and Death 101 (2007). The quirky comedy follows the sexual odysseys of successful businessman Roderick Blank (Simon Baker) who receives a mysterious e-mail on the eve of his wedding, listing all of his past and future sex partners. Convinced that his marriage would deter a mind-blowing future path of bachelorhood, Roderick sets out to find all the listed women and fulfill his destiny of one-night stands. Things take a fatal turn courtesy of Ryder's paramour/femme fatale Death Nell, a woman who enjoys near-fatal trysts with her love partners along with the intent on punishing all men she finds guilty of sex crimes against women. Filming wrapped July 6, 2006, and is set for release in early mid-Spring 2007.
In July 2006, Entertainment Weekly reported that Ryder and writer/director Daniel Waters are also working on ideas for a Heathers sequel. "We will be doing a sequel to Heathers next", Ryder said. "There's Heathers in the real world! We have to keep going!" In a recent interview for Entertainment Weekly Ryder was quoted as saying,
“
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.
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Waters is writing the sequel, and may also direct.
Ryder will soon appear in David Wain's new comedy The Ten, along with Jessica Alba, Paul Rudd, Justin Theroux, Famke Janssen, Oliver Platt, and Adam Brody. The film centers around 10 stories, each inspired by one of the Ten Commandments. Filming wrapped on September 7, 2006. The film debuted at the Sundance Film Festival 2007 on January 19, and was picked up by ThinkFilm. Release date is set for August 3rd 2007.
According to Production Weekly Winona will play the female lead opposite Wes Bentley and Ray Romano in Geoffrey Haley’s offbeat romantic dramadey“The Last Word.�[] Haley will direct his own script about a reclusive writer played by Bentley, who makes his living composing other people’s suicide notes. His life gets turned upside down after he embarks on a tumultuous romance with Ryder, the sister of a recently deceased client. Filming is set commence later this month in Los Angeles.
Shoplifting incident
On December 12, 2001, Ryder was arrested for shoplifting thousands of dollars' worth of designer clothes and accessories at Saks Fifth Avenue department store in Beverly Hills, California. Los Angeles District Attorney Stephen Cooley set up a team of eight prosecutors and seized the opportunity to prosecute the actress aggressively. He filed four felony charges against her in what was described by The Guardian (UK) as a show-trial since the prosecution demanded the trial be televised. Ryder hired noted 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 5000 other defendants in similar cases, an open door to a no-contest plea on misdemeanor charges.
During the trial, she was also accused of using drugs without valid prescriptions. According to a probation report that can be found on the The Smoking Gun website, she had filled up to 37 prescriptions written by 20 doctors, using six different aliases, in a three-year period. The defense produced the written prescriptions for the drugs that the police found in her purse, and the prosecution consequently dropped the charge. Ryder was convicted of grand theft and vandalism, but the jury acquitted her 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 Saks—and the judge ordered the actress to attend psychological and drug counselling.
The charges were eventually reviewed, and on June 18, 2004 the felonies were reduced to misdemeanors.
Personal life
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Ryder was engaged to actor Johnny Depp for three years. During their relationship, Depp got a tattoo on his arm reading "Winona Forever," which he had altered to "Wino Forever" after their breakup. Ryder later had serious relationships with Soul Asylum's Dave Pirner and actor Matt Damon (engaged at one time in 2000).
Polly Klaas
In 1993, Ryder became involved in the Polly Klaas kidnapping case. Klaas lived in the same town where Ryder grew up, Petaluma. Ryder offered a $200,000 reward for the 12 year-old kidnap victim's safe return. After Polly's death, Ryder starred in a film version of Little Women and dedicated it to her memory. The Louisa May Alcott novel was Polly's favorite book. The producers at first wanted to remove the dedication, but Ryder said she would not do any publicity for the film if it was removed, so it was retained.
In December 2002, during Ryder's sentencing for shoplifting, her attorney Mark Geragos detailed Ryder's efforts in the Klass kidnapping during his defense arguments. DA assistant Ann Rundle then accused Ryder of "building her career over the body of a dead child." Ryder was visibly upset by the accusation. Mark Klaas, Polly's father, was expelled from the courtroom while attempting to voice protest.
Trademark
Often plays a bizarre, unconventional girl who is a round peg amidst a bunch of square ones. She then gets thrust into a new and strange world where she fits in and finds her true niche.
Often has a diary and writes in it throughout the course of the film, almost playing the part of narrator.
