2000

Winona Ryder

January 14

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

Winona Ryder

December

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

Winona Ryder

June

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

Winona Ryder

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 Ryder

August

Blockbuster Comeback

After stepping out with Rilo Kiley guitarist Blake Sennett, Ryder breaks her silence about her shoplifting snafu to Vogue, laying 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, topping it off with the blockbuster Star Trek, where she plays Spock's mom.

2010

Winona Ryder

December

Tutu Crazy

Ryder takes on a cameo role in the Oscar-nominated drama Black Swan, playing Beth, a prima ballerina on the way out. "I did relate to Beth on a certain level. Just the thing of, you know, when I’m told I’m not the ingénue anymore," Ryder tells Elle of her character, who's replaced in the company by up-and-coming dancer Natalie Portman.

2011

Winona Ryder

January 14

Winona's 'Dilemma'

"It's amazing! Really one of the highlights of my career in acting," Ryder says of working with Oscar-winning director Ron Howard in the comedy, The Dilemma, in which she's caught having an affair (with Channing Tatum) by her husband's best friend (played by Vince Vaughn). "You should've seen me when I got the phone call [when I cast], I was jumping up and down like a kid."

2013

Winona Ryder

May

Back At It

Ryder returns to her indie roots – and leading lady status – with The Iceman, a drama about contract killer Richard Kuklinski. "Every time I hear 'comeback, blah, blah, blah,' it’s kind of hard for me … There is a little bit of defensiveness because I do feel like I have contributed," she tells Interview magazine, in which she also opens up about her 2011 shoplifting arrest. "I think a lot of people think that that is what sort of sent me off in another direction, but I was actually starting to have some trouble a few years before," she says. "In a weird way, it was almost like the best thing that could have happened because I’d never asked myself the question before of, 'Is it okay if I'm not going to act? Is there anything else?’ because that was all that I really knew."

Photo Credits

BIOGRAPHY (top to bottom): Columbia Pictures; Everett Collection; Eric Ryan/Getty; Everett Collection; Millennium Entertainment

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)
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Edited by Julia Wang

Winona Ryder

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