- 2000
Girl, Interrupted
Ryder stars in the coming-of-age mental hospital drama Girl, Interrupted. Director James Mangold tells the New York Times, "[Ryder] gives a wonderful performance because she understood that the point of the book is that crazy isn't all that different from normal." Her performance is called Oscar-worthy, but it's her costar Angelina Jolie (left) who wins the Best Supporting Actress Oscar.
- 2001
Caught on Tape
Ryder is caught on videotape and arrested for shoplifting $4,760 worth of merchandise at Saks Fifth Avenue in Beverly Hills. She's also arrested with an alarming amount of prescription painkillers (eight different varieties). Her case makes headlines and she spoofs herself on Saturday Night Live, pretending to steal items and scenes from the cast.
- 2002
Free Winona!
Ryder poses for W wearing a "Free Winona" T-shirt, which becomes a hot seller online. During her trial, prosecutors are banned from presenting surveillance-camera evidence of three previous incidents in which Ryder reportedly shoplifted. In the chaos outside court, a TV camera slams into Ryder and breaks her arm. She's fitted for an arm sling, which becomes part of her daily attire – along with demure Marc Jacobs outfits. The first-time offender is convicted of grand theft and vandalism: She's ordered to perform 480 hours of community service, sentenced to three years' probation, fined more than $16,000, and has to attend psychological and drug counseling. Her felonies are later reduced to misdemeanors.
- 2006
Out of the Dark
After lying low in San Francisco, Ryder makes her first major film since her trial in the rotoscoped film, Scanner Darkly with Keanu Reeves (right), and Robert Downey Jr. The limited-release film earns positive reviews. "Usually the movies I do for a lot less money are the ones that I end up enjoying more," she confides to Canada's National Post. "I felt lucky every day that I was there."
- 2007
Winona's Back!
Ryder finally breaks her silence in a Vogue interview. She lays most of the blame on her "sort-of quack doctor" whom she says over-prescribed Oxycodone. "I don't have this tremendous sense of guilt [for shoplifting], because I hadn't hurt anyone," she says. The actress slowly rebuilds her career with a string of small comedies and one highly-anticipated blockbuster, J.J. Abrams' Star Trek, where she'll play Spock's mom. She also steps out with boyfriend, Blake Sennett (left), guitarist for Rilo Kiley – whom she dates until 2008.
Photo Credits
BIOGRAPHY (top to bottom): Columbia Pictures; Everett Collection; Eric Ryan/Getty
- Name
- Winona Ryder
- Date of Birth
- October 29, 1971
- Birth Place
- Winona, Minnesota
- Relationships
-
Blake Sennett, ex-boyfriend (2007 to 2008)
Henry-Alex Rubin, ex-boyfriend (2006)
Page Hamilton, ex-boyfriend (2003)
Matt Damon, ex-boyfriend (1997 to 2000)
David Pirner, ex-boyfriend (1993 to 1997)
Johnny Depp, ex-boyfriend (1989 to 1993; engaged)
