Only in recent years has Ryder opened up about it all - her shoplifting in 2001, the court case that ensued, and why she disappeared from the entertainment industry. But even while opening up, Ryder has said she is still "processing a lot". Namely, she's still figuring out how to deal with fame and all that comes with it.
By the time she was 18, Ryder was a household name. Throughout the 90s, the press poured over every detail of her life - her relationship with Johnny Depp, her films, her body, and more.
"I know it's kind of like 'Oh, poor Winona'," she said. "But when you're in pain, pain is pain. But that realisation took me a while. This business is brutal. You're working constantly, but if you want to take a break, they tell you, 'If you slow down, it's going to stop'."
And stop it did.
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On December 12, 2001, Ryder was arrested for shoplifting in Beverly Hills, California after stealing $5,500 worth of designer clothing from Saks Fifth Avenue. At the time of her arrest, the then 30-year-old was a household name, with films such as Heathers, Beetlejuice, and Edward Scissorhands under her belt.
After a six-day trial in 2002, Ryder was found guilty of grand theft and vandalism, and sentenced to three years probation, 480 hours of community service, and fined $3,700.
Immediately, Ryder's long list of mainstream leading roles dwindled and she seemingly vanishing from the public eye.